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The Word on Pop Culture's 100 Best Songs Since 2000

10/6/2025

by Charles Bell, Tyler Glover, Aprille Hanson-Spivey & Julian Spivey

100. "Mud on the Tires" by Brad Paisley (2003)
Album: Mud on the Tires
Songwriters: Brad Paisley & Chris DuBois

From 1999 to the early 2010s, Brad Paisley owned country music. He dominated radio stations with more than 50 charted singles for Billboard’s country singles chart and pumped out albums every year or two years from 1999 to 2014, with his last album dropping in 2017. With a stellar voice and remarkable guitar skills, he was the perfect combination of revering true country music, while also putting his own modern and often humorous spin on it. While he has been out of mainstream country for a while, aside from occasional appearances on award shows for duets, his impact on the genre today remains immense. I could fill up this list with stellar Paisley tunes, from the humorous “I’m Gonna Miss Her (The Fishin’ Song)” to the more profound “Welcome to the Future,” but “Mud on the Tires” is my choice. The title track of his 2003 album, one of his two albums that were certified double platinum, reached No. 1 on the Billboard country charts in 2004. It is a fun, romantic, truck-infused song that didn’t make you want to roll your eyes, written by Paisley and Chris Dubois. Lyrically, it paints a beautiful picture of a couple celebrating their purchase of “a brand new Chevrolet” and taking off to get “a little mud on the tires,” down dirt roads with crickets and campfires. It has the same Southern charm as Nitty Gritty Dirt Band’s “Fishin’ in the Dark.” Paisley’s silky drawl and superior guitar riff toward the end help solidify it as one of his best and one of the best of the genre, standing out high above a sea of clichéd truck anthems today. AHS

99. "Empire State of Mind" by Jay-Z & Alicia Keys (2009)
Album: The Blueprint 3
Songwriters: Shawn Carter, Alicia Keys, Alexander Shuckburgh, Janet Sewell-Ulepic, Angela Hunte, Sylvia Robinson & Bert Keyes

I’ve always admired how much New Yorkers appreciate their state. Nothing embodies New York pride quite like "Empire State of Mind" by Jay-Z and Alicia Keys. This song is iconic for various reasons, from the lyrics to the shots in the video. I believe the primary reason this song is iconic is the hope it brought not only to the hip-hop community but also to communities worldwide. If you go back to when this song was released, we were experiencing a once-in-a-century economic crisis. Newly elected President Barack Obama ran a campaign discussing hope for the future. Although this song was mainly about New York, I think hearing the words in Keys’s iconic voice, “There’s nothing you can’t do,” resonated with so many people at the time. If you think about some of the more iconic songs throughout our time, you can always relate them to a specific period or situation. The 2000s era of hip hop was truly special. A great argument can be made that this song capped that era. CB

98. "Crazy in Love" by Beyoncé feat. Jay-Z (2003)
Album: Dangerously in Love
Songwriters: Beyoncé Knowles, Shawn Carter, Rich Harrison & Eugene Record

A list of the best songs of the last 25 years would not be complete without including “Crazy in Love” by Beyoncé featuring her now-husband, JAY-Z. “Crazy in Love” was the lead single from Beyoncé’s first solo debut album, Dangerously in Love. It was very sad to hear that Beyoncé was leaving her incredibly successful group, Destiny’s Child. However, from the moment her first solo single played, you could argue that maybe she should have been doing this by herself all along. “Crazy in Love” went No. 1 on the Billboard Hot 100 for eight consecutive weeks and would go on to win two Grammy awards: Best R&B Song and Best Rap/Sung Collaboration. In 2018, Billboard ranked this song as the Best Song of the 21st century so far. This is the perfect song to get out on the dance floor on a Friday night after a long week at work. It isn’t just any dance song, though; “Crazy in Love” manages to do something that so many songs set out to do but don’t consistently achieve. It managed to become iconic, instantly memorable, and so catchy that it ensured everyone would go “crazy!” You would not think a song that says “uh-oh, uh-oh, uh-oh, uh-oh, uh-oh" to a specific beat would leave such a lasting impact, but it does. This song captures the feelings that we can have for someone who manages to make us become crazy and unlike ourselves. We will do things out of the ordinary because of the connection we have with this person. Music has a way of evoking a wide range of emotions, and every song serves a distinct purpose. This song brings us joy. It may have come out way back in 2003, but dance parties around the world are still completing their setlist with this blockbuster hit. TG

97. "This Land" by Gary Clark Jr. (2019)
Album: This Land
Songwriter: Gary Clark Jr.

Gary Clark Jr. has taken up the mantle as the best blues-rock guitarist of his generation, and his blues are more than the old-school “she done me wrong” trope. The modern world comes with its own kind of blues – the being treated like an other when you’re just trying to survive a crazy and cruel world. Clark experiences this in “This Land,” off his 2019 album of the same name, which was inspired by an incident with a neighbor who repeatedly asked who lived on Clark’s 50-acre property in Austin, Texas, not believing that Clark, a black man, could own the home. Clark takes on the upsurge in hate and racism experienced during the Trump years, whom he name-drops. The song, which also has a terrific remix version with The Roots, including an opening rap by Black Thought, won Clark Grammys for Best Rock Song and Best Rock Performance. JS

96. "Simple Song" by The Shins (2012)
Album: Port of Morrow
Songwriter: James Mercer

The Shins will likely forever be primarily known for their 2001 indie classic, “New Slang,” and its appearance in Zach Braff’s 2004 film, “Garden State.” While that’s a terrific song, I think the best track the band has ever produced is “Simple Song,” from its 2012 album Port of Morrow. Much like how “New Slang” hit it big after its inclusion in “Garden State,” it was the inclusion of “Simple Song” in another artform (though on a smaller scale) – the finale of the penultimate season of “How I Met Your Mother” – that introduced the song to me. I’ve been in love with it ever since. “Simple Song” tells the story of blossoming love and was inspired by frontman/songwriter James Mercer’s marriage and early relationship period leading up to the birth of their first daughter. The way the music builds to its raucous ending effectively mimics the feelings of love that often emerge early in a relationship. It’s a beauty. JS

95. "Hero" by Enrique Iglesias (2001)
Album: Escape
Songwriters: Enrique Iglesias, Paul Barry & Mark Taylor

In 2001, I was a young teenager who just wanted to be loved. I wanted to have a girlfriend like everyone else did. Looking back now, I know that I wasn’t falling for anyone. I was just in love with being in love. Every love song that hit the radio felt like it was made for this hopeless romantic and his future love. That is why when “Hero” by Enrique Iglesias came out, it was the perfect song for me. The Spanish singer-songwriter touches on the universal feeling of wanting to be the hero for the one we love. The singer is pleading with them to let them be that person for them. The song reached No. 3 on the Billboard Hot 100 and became extremely popular. While this song is a fantastic love song, the main reason it must be included on this list is the significant role it plays in American history. This song was released eight days before the September 11th terrorist attacks on the World Trade Center and the Pentagon. “Hero” is one of the few songs chosen by radio DJs in New York City to be remixed with audio from police, firefighters and civilians at Ground Zero. Iglesias was even asked to sing the song live for the televised benefit concert “America: Tribute to Heroes.” When I hear this song now as an adult, it makes me think of those we lost in those acts of violence against our country and the heroes that we saw that day. Men and women who did not come home to try to save other people, answering the call of duty. They will always be our heroes. TG

94. "Last Nite" by The Strokes (2001)
Album: Is This It
Songwriter: Julian Casablancas

When The Strokes burst onto the scene in late 2001 with “Last Nite,” it felt both of its time and timeless—maybe it was that kickass opening guitar riff that borrowed heavily from Tom Petty & the Heartbreakers’ classic “American Girl.” It was the type of rock music you want pulsating through your veins. The band openly admitted they ripped off the classic rock riff with frontman/songwriter Julian Casablancas saying, “People would say, ‘You know that song ‘American Girl’ by Tom Petty? Don’t you think it sounds a little like that?’ And I’d be like, ‘Yeah, we ripped it off. Where you been?.” Rolling Stone ranked “Last Nite” as the 155th greatest song of all time in 2001, 14 spots higher than “American Girl,” which I disagree with, but it’s still a fantastic song. JS

93. "Texas Hold 'Em" by Beyoncé (2024)
Album: Cowboy Carter
Songwriters: Beyoncé Knowles, Brian Bates, Elizabeth Lowell Boland, Atia Boggs, Megan Bülow, Nathan Ferraro & Raphael Saadiq

“Texas Hold ‘Em,” one of two singles first released off Beyonce’s country album Cowboy Carter, is one of the most important songs of the last 25 years because you have a larger-than-life artist creating an album full of Americana flavor, and at its core, a celebration of Black music. Debating whether the album is country or not misses the point. The 27-track album encompasses a diverse range of genres, from country to opera, pop to rap, and even a touch of Western influence, all with a hint of Beyoncé flair. She’s one of the most accomplished artists of our time, and this album is a big statement when it comes to genres and whether or not artists should be put in a box. Beyoncé has proven again that she can’t be contained. And unlike some country artists today who don’t get near the scrutiny she has, Beyoncé was born and raised in Houston. Written by Beyoncé and six other writers, Brian Bates, Elizabeth Lowell Boland, Atia Boggs, Megan Bülow, Nathan Ferraro, and Raphael Saadiq, it reached No. 1 on both the Billboard Hot 100 and country charts. It has a fun Texas swing to it, with lyrics like, “This ain't Texas (woo), ain't no hold 'em (hey) / So lay your cards down, down, down, down.” She dives into a few Southern cliches, like rugged whiskey and a hoedown, but there’s no mention of a truck. In this case, it’s a Lexus. A gem of the track is the masterful musician Rhiannon Giddens, who plays banjo and viola. It’s a song that hooks you with its soul, playfulness and catchy lyrics. AHS

92. "Good Luck, Babe!" by Chappell Roan (2024)
Album: Non-Album Single
Songwriters: Chappell Roan, Justin Tranter & Dan Nigro

Chappell Roan is an artist that many of my Swiftie friends began listening to last summer. They kept telling me to check into her and that if I loved Taylor Swift, I would love Chappell Roan as well. It took me a few weeks, but after hearing numerous publications proclaim Chappell Roan as “your favorite artist’s favorite artist,” I knew I had to give her a chance. Chappell Roan has quickly become one of the most exciting new artists in recent years. This past February, she won the Grammy for Best New Artist and was nominated for Album of the Year for her smash hit album, The Rise and Fall of a Midwest Princess. Her hit song, “Good Luck, Babe!” would also be nominated for Record and Song of the Year. Quite simply, it should have won at least one, if not both, of those awards. “Good Luck, Babe!” was my favorite song of 2024. In this song, Chappell Roan sings about how a girl she loves is denying the feelings she has for her. She tells her that she can “kiss a hundred boys in bars,” but she won’t get over her. My favorite lyric in the song is “You have to stop the world just to stop the feeling.” So many of us think that we can “turn off” our genuine feelings of love for someone, and it just isn’t possible. If you love someone, you love them. You only hurt yourself by denying it. This song is such a banger and will be remembered for years to come for its uniqueness and blunt honesty. TG

91. "I Am a Man of Constant Sorrow" by The Soggy Bottom Boys (2000)
Album: O Brother, Where Art Thou?
Songwriter: Traditional (Unknown)

It’s wild to think that there was such a big bluegrass craze reborn by the Coen Brothers' 2000 film “O Brother, Where Art Thou” that the film's soundtrack won the Grammy Award for Album of the Year. The highlight of that soundtrack was an, at the time, almost 100-year-old traditional folk song called “I Am a Man of Constant Sorrow,” usually called “Man of Constant Sorrow” in its previous recordings, which include one on Bob Dylan’s self-titled debut album in 1962. In the film, George Clooney’s character, Ulysses Everett McGill, is performing the song. In reality, he was lip syncing to Dan Tyminski, a performer in Alison Krauss’ talented Union Station band. Tyminski’s beautifully twangy vocals, mixed with the superb musicianship on the record, helped bring a genre and sound unknown to many outside of Appalachia to the forefront of American music. JS

90. "Slow Motion" by Juvenile feat. Soulja Slim
Album: Juve the Great
Songwriters: Juvenile & Soulja Slim

In my lifetime, the decade from 2000 to 2009 was the best for hip hop. I wasn’t around for much of the '80s, and I was just a kid in the '90s, so I might be biased toward my own era. This era was so special because of the competition not only from various artists but also the singles they were constantly producing. These days, the term “hit” is used way too loosely when it comes to music. It seems like every song released is referred to as a hit. “Slow Motion” by Juvenile is a TRUE hit. The song can be identified within its first three seconds. I have friends from all backgrounds, and even in 2025, that song is still popular. During this era of hip-hop, a shift occurred from the classic gangsta rap to a smoother, calmer approach. Juvenile took that to the next level with “Slow Motion.” If you go out to a party, bar or any similar atmosphere, there is a good chance you will hear this song and it’ll receive plenty of recognition from the crowd. I consider “Slow Motion” to be a hype song, which is wild considering its slower-paced beat. This type of song, being able to ignite a crowd, is a testament to its exceptional quality. CB

89. "American Skin (41 Shots)" by Bruce Springsteen (2001)
Album: Live from New York City
Songwriter: Bruce Springsteen

The legendary songwriters don’t shy away from the harsh realities and truths of the real world. Bruce Springsteen has rubbed some more conservative-leaning music fans the wrong way due to his political views. He’s never been more political in a song than 2001’s “American Skin (41 Shots),” which he debuted in concert in mid-2000, first appeared on the live album Live in New York City in 2001, and didn’t have a studio version until it appeared on High Hopes in 2014. The song took on the NYPD shooting death of Amadou Diallo, an unarmed Guinean immigrant, in February 1999, doing so from the perspective of a mother warning her child of color how to act around police and the perspective of the police. Despite not be an anti-police song, it sure pissed off some, with the NYPD’s police commissioner calling for a boycott of Springsteen’s New York City shows at that time. Rudy Giuliani, then the Mayor of New York City, condemned the song and asked Springsteen not to play it in New York. Not only did Springsteen play it, but it also ended up on the live album. JS

88. "Austin" by Blake Shelton (2001)
Album: Blake Shelton
Songwriter: David Kent & Kirsti Manna

I’m going to say it – long-haired Blake Shelton is my favorite version of all the metamorphoses he’s gone through as an artist. He’s never lost that deep, smooth voice, but his musical style has certainly evolved. It’s not a bad thing for artists to branch out musically but give me “Some Beach” over “Boys ‘Round Here” or “Ol’ Red” over “Hillbilly Bone,” every time. “Austin” was his debut single in 2001, hitting No. 1 on the Billboard Country charts for five weeks. Written by David Kent and Kirsti Manna, it’s about a woman who, in today’s terms, we’d say ghosted a man without even leaving her number. Of course, this was back before social media and smartphones, when ghosting was a legit thing. He suspected she went back to Austin “'cause she talked about it all the time.” So, a year later, the woman decides to call him back, but he's not home; she gets his answering machine. Then enters Shelton with his powerhouse voice, listing off the man’s voicemail greeting, “If you’re callin’ ‘bout the car, I sold it / If this is Tuesday night, I’m bowling / If you’ve got somethin’ to sell you’re wasting your time, I’m not buyin’ / If it’s anybody else, wait for the tone / You know what to do / And P.S. if this is Austin, I still love you.” Chills. It’s either deeply romantic that this man has pined for her for a year or disconcerting. Luckily for the listener, Shelton’s delivery makes it uniquely romantic. We will, for love, ignore the improbability that anyone would change their voicemail message that often. The couple gets their happily ever after, and we get one of the best songs of the last 25 years. AHS

87. "Drivers License" by Olivia Rodrigo (2021)
Album: Sour
Songwriters: Olivia Rodrigo & Dan Nigro

Olivia Rodrigo’s “drivers license” is a devastating song of young heartbreak. Rodrigo sings that she is excited to get her driver’s license so that she can drive to her boyfriend’s house in the suburbs. However, by the time she gets it, he has moved on to that “blonde girl” who always made her doubt. This song has two lyrics that gut me every time I hear them: “I just can’t imagine how you could be so okay now that I’m gone,” and “I know we weren’t perfect, but I’ve never felt this way for no one.” Even as an adult, it is devastating to love someone who will never choose you. For them, it may be easy to move on, but for you, it may have meant that they were your soulmate. How do you even remotely start to get past those conflicting emotions, knowing that there is nothing that can happen in reality about it? “drivers license” is the song that launched Olivia Rodrigo’s career. It reached No. 1 on the Billboard Hot 100, making her the youngest artist to ever debut at the top spot. Rodrigo went on to win Best New Artist at the 2022 Grammys, and this song won Best Pop Solo Performance. “drivers license” was also listed in 2024 in Rolling Stone’s 500 Greatest Songs of All Time list at No. 377. TG

86. "Crazy" by Gnarls Barkley (2006)
Album: St. Elsewhere
Songwriters: CeeLo Green, Danger Mouse, Gian Franco Reverberi & Gian Piero Reverberi

“Crazy,” the 2006 debut single from Gnarls Barkley – the duo of singer-songwriter CeeLo Green and producer Danger Mouse – is a perfect mixture of soul, funk, R&B and electronica to form a great pop single. The lyrics came from a conversation between Green and Danger Mouse in which Danger Mouse was talking about how artists are not taken seriously unless they’re insane. Green took the conversation and turned it into a song. The song's music was inspired by Spaghetti Western scores, especially those made famous by composer Ennio Morricone. Rolling Stone magazine named “Crazy” the best song of the decade from 2000 to 2009. JS

85. "Don't Know Why" by Norah Jones (2002)
Album: Come Away With Me
Songwriter: Jesse Harris

Norah Jones briefly made jazz pop one of the biggest sounds in popular music with her 2002 debut album Come Away with Me, which hit No. 1 on the Billboard albums chart and featured the lovely single, “Don’t Know Why,” which surprisingly looking back only peaked at No. 30 on the Billboard Hot 100. The smooth, jazzy ballad by Jones, written by Jesse Harris and originally appearing on his 1999 album Jesse Harris & the Ferdinandos cleaned up at the Grammy Awards in early 2003, winning Record of the Year, Song of the Year, and Best Female Pop Vocal Performance. Come Away with Me won Album of the Year. More than 20 years later, “Don’t Know Why” is still one of the sweetest-sounding vocal performances you’ll ever hear. JS

84. "Get the Party Started" by Pink (2001)
Album: Missundaztood
Songwriter: Linda Perry

I would never claim to be a major Pink fan. I have great respect for her as an artist, the way she champions the underdog and just her masterful way of entertaining a crowd – singing while doing acrobatics will always be impressive. “Get the Party Started,” written by Linda Perry, was released in 2001 on her second album, Missundaztood. It reached the top 10 on charts in several countries internationally, and No. 4 on the Billboard Hot 100 in 2001. If you were a pre-teen or teenager in the early 2000s, all you had to do was hear her laugh and that opening bouncy melody, and you knew what song it was, kicking it off with “I’m comin’ up so you better get this party started.” It’s a party pop song, but it’s also got that signature edge Pink is known for. That’s really what makes it stand out years later. There are a lot of cliché party pop songs, but not many say things like, “I’ll be burnin’ rubber, you’ll be kissin’ my ass.” It’s not like the lyrics are anything spectacular but combine it with her rasp-tinged voice and the melody, and it’s just a badass party song. The song was initially meant for Madonna on her 2000 album Music, but she declined. Nothing against Madonna, but this song was perfect for Pink. AHS

83. "Copper Canteen" by James McMurtry (2015)
Album: Complicated Game
Songwriter: James McMurtry

James McMurtry is one of the best storytellers in the music business. Perhaps it runs in his family, as his father, the novelist Larry McMurtry, is known for his works, such as Lonesome Dove. McMurtry writes the kind of songs that you can see in your mind’s eye as if you’re watching a film. My favorite story-song by McMurtry is “Copper Canteen” from his 2015 album, Complicated Game. “Copper Canteen” is the tale of an aging married couple nearing retirement age, struggling with the ups and downs of small-town life. Although their love may not be as bright as it once was, they depend on each other to get by. It’s a lyrical masterpiece. - JS

82. "Roar" by Katy Perry (2013)
Album: Prism
Songwriters: Katy Perry, Lukasz Gottwald, Max Martin, Bonnie McKee & Henry Walter

Sometimes, the world needs a great anthem song. It requires a song to sing to help us exude confidence, feel pumped up, and find the resilience we need to face the harshness of the world we live in. Katy Perry had already proven herself to be a huge pop star with her second studio album, Teenage Dream, tying Michael Jackson’s record for the most No. 1 hit singles on the Billboard Hot 100 from one album with five. “Firework,” especially, had proven that she had a massive talent for producing epic anthem songs. I thought “Firework” would honestly be the best she ever had, but I was proven wrong with her next hit from her third album: “Roar.” “Roar” is the absolute perfect song to play when you are trying to prepare yourself for difficult stuff. When you sing, “I got the eye of the tiger, the fire, dancing through the fire cause I am a champion, and you’re gonna hear me ROAR,” you KNOW everything is going to be OK. You begin to feel sorry for the person who will have to deal with you. TG

81. "Truth Hurts" by Lizzo (2019)
Album: Cuz I Love You (Deluxe)
Songwriters: Melissa Jefferson, Eric Frederic, Jesse Saint John, Steven Cheung & Amina Bogle-Barriteau

It’s hard to believe “Truth Hurts” by Lizzo was initially released in 2017 with not much fanfare. In 2019, it found new life on TikTok, making it Lizzo’s first No. 1 hit on the Billboard Hot 100. It had a historic seven-week run at the top. It won a Grammy for Best Pop Solo Performance in 2020 after being included as a bonus track for the deluxe release of her third album, Cuz I Love You, in 2019. The song was penned by Melissa Jefferson (Lizzo), Eric Frederic, Jesse Saint John, Steven Cheung and Amina Bogle-Barriteau and fits Lizzo’s badass-girl-power persona perfectly. The opening lines create the perfect earworm: “Why men great ’til they gotta be great / Woo! / I just took a DNA test, turns out, I’m 100% that bitch / Even when I’m crying crazy / Yeah I got boy problems, that’s the human in me / Bling, bling then I solve ’em, that’s the goddess in me.” “Truth Hurts” is incredibly catchy, and if a woman needs a pick-me-up, it’s a go-to. Lizzo has a way of making every woman listening feel invincible. AHS

80. "Outlaw Band" by Jason Boland & the Stragglers (2010)
Songwriters: Bob Childers, Randy Crouch & Layle Stagner
Album: High in the Rockies: A Live Album

“Outlaw Band” is probably my favorite live show closer ever, and it’s one I’ve seen many times from red dirt country legends Jason Boland & the Stragglers. They cut the song, written by Bob Childers, Randy Crouch and Layle Stagner, for their sixth studio album Comal County Blue in 2008, but the best recording is the live version that wraps 2010’s High in the Rockies: A Live Album. The song tells the tale of a group of friends – all of them loners – who formed a band in the ‘60s and like to play all night long. The song culminates in one of my all-time favorite fiddle performances by Noah Jeffries, on the record (though I never saw him play it live), who also plays exquisite mandolin on the song. JS

79. "Work It" by Missy Elliott (2002)
Album: Under Construction
Songwriters: Melissa Elliott & Timothy Mosley

When Missy Elliott released “Work It” in 2002, it further solidified her as a top star in Hip Hop. I’ve said previously that I think the 2000-2008 era was the best in Hip Hop, due to the quality of music and the caliber of artists. Notice I said it solidified her as a top star and not a top female star. The song “Work It” is known for its iconic hook and, most notably, how she recites the lyrics in reverse. You can hear this song in various places in 2025, which demonstrates its enduring popularity. A few years ago, Missy Elliott surprised us as she was on stage at the Super Bowl and saw her streaming numbers increase due to the performance of “Work It.” You even had those who thought Missy was a new artist and the song was a new hit, talk about a generational gap. That shows how powerful that song is, especially for my generation, 20-plus years later. CB

78. "Thinking Out Loud" by Ed Sheeran (2014)
Album: x
Songwriters: Ed Sheeran & Amy Wadge

Ed Sheeran is my current favorite male artist. With Sheeran, you always feel his heart and authenticity in every song he releases. Whether it's a love ballad or a song about the death of a loved one, he knows how to infuse the lyrics and arrangement with maximum sentimental value. I have found myself crying through many of his incredible songs over the years. It was "Thinking Out Loud," though, that managed to take Sheeran's career to new heights. In 2016, Sheeran won the Grammy for Song of the Year and Best Pop Solo Performance for "Thinking Out Loud." It is such a beautiful love song. Every lyric sounds like it could be in a poem written by someone madly in love or part of a monologue in a romantic comedy film. Shockingly, "Thinking Out Loud" did not go to No. 1 on the Billboard Hot 100; it did peak at No. 2. In an age of music where lyrics are sexually explicit and feel devoid of emotion, Sheeran excels at showing us that old-fashioned romance is not dead. TG

77. "American Idiot" by Green Day (2004)
Album: American Idiot
Songwriter: Billie Joe Armstrong

Green Day’s “American Idiot,” the title track off their Grammy-nominated punk rock opera album of the same name, was both of its time and, unfortunately, still completely relevant more than 20 years after its release. It came about as a protest of President George W. Bush's administration and its controversial war in Iraq, and the rah-rah patriotic media coverage following 9/11 that helped ramp up American interest in such a war. More than two decades later, the band has updated the once-relevant lyric, “I’m not a part of a redneck agenda,” to the now-relevant, “I’m not a part of a MAGA agenda,” referencing how some things may not change or even worsen with time. JS

76. "Anything But Mine" by Kenny Chesney (2004)
Album: When the Sun Goes Down
Songwriter: Scooter Carusoe

Kenny Chesney has demonstrated a remarkable talent for selecting outstanding songs that match his sound and vibe, and Scooter Carusoe’s “Anything but Mine” stands out as the best of his career. The No. 1 hit from 2004’s When the Sun Goes Down tells the story of a fleeting summer romance and the final night of that relationship, where the narrator hopes to create a lasting memory before heading back home. It’s one of the most powerful portrayals of young love and raw emotion set to music. JS

75. "Since U Been Gone" by Kelly Clarkson (2004)
Album: Breakaway
Songwriters: Max Martin & Lukasz Gottwald

Kelly Clarkson has the unique honor of being the first “American Idol” winner in a sea of artists who have since captured that once-coveted title. While many winners have faded into obscurity, Clarkson’s powerful voice and artistry have built a lasting legacy, making ‘Idol' a distant memory. When I think of classic Clarkson, I always think of "Since U Been Gone.” Written by Max Martin and Lukasz Gottwald and released in 2004 on her second album, Breakaway, it’s a female empowerment song about feeling free to “breathe for the first time” after a breakup. Although many songs like this have existed over the years, Clarkson’s strong, crystal-clear vocals and wide range make it stand out. The choruses match the mood of heartbreak, with her low alto conveying sadness, then exploding into high notes as the song intensifies. She practically screams the bridge, “You had your chance, you blew it / Out of sight, out of mind / Shut your mouth, I just can’t take it / Again and again and again and again," on pitch. The song was initially rejected by Pink, then Hilary Duff when she couldn’t hit the high notes. Clarkson made it her own by adding heavier guitar sounds and drums, which proved to be a perfect choice. With Clarkson as the lead, these decisions turned this song into one of the best since 2000. AHS

74. "Not Ready to Make Nice" by The Chicks (2006)
Album: Taking the Long Way
Songwriters: Martie Maguire, Natalie Maines, Emily Robison & Dan Wilson

There is no doubt: we are living in a very divided country. It had long been a tradition for celebrities and musicians to stay silent about their political views to avoid alienating their fans or harming their careers. In 2025, it may not be surprising for a celebrity to share their politics, but in 2003, the lead singer of the Chicks, Natalie Maines, told a crowd she was ashamed that then-President George W. Bush was from their home state of Texas. The backlash was almost immediate. The Chicks faced death threats and people shouting that they should just "shut up and sing." Their careers seemed headed for an early end. However, on March 20, 2006, they released their powerful song, "Not Ready to Make Nice," in response to the criticism they endured. It took courage to express their beliefs when doing so wasn't the popular choice. "Not Ready to Make Nice" captures their complex feelings during the backlash. Most of us are told it's okay to accept an apology, but when you’re receiving death threats for sharing your opinions, overcoming that is much harder. This song states that the Chicks were not ready to forgive or forget. They remained "mad as hell" and believed "it's too late to make it right," and they probably wouldn't even if they could. "Not Ready to Make Nice" went on to win Record and Song of the Year at the Grammys, along with Best Country Performance by a Duo or Group With Vocals. TG

73. "It's Five O'Clock Somewhere" by Alan Jackson feat. Jimmy Buffett (2003)
Album: Greatest Hits, Vol. II
Songwriters: Jim "Moose" Brown & Don Rollins

Jimmy Buffett was one of the artists who was always kind of on an island of his own —figuratively and sometimes literally. Musically, he doesn’t really fit into country, rock or folk, but has a more beach-Americana flavor, but it’s not like he only sang about tropical life. Any way you want to characterize the late legend, he finally received more widespread acclaim 26 years after his massive hit “Margaritaville” with the Alan Jackson duet, “It’s Five O’Clock Somewhere.” Released in 2003 and written by Jim “Moose” Brown and Don Rollins, it was released on Jackson’s compilation album, “Greatest Hits Volume II.” It was No. 1 for eight non-consecutive weeks on the Billboard Hot Country Songs in the summer of 2003. It earned Buffett his first award in his career at that time with the Country Music Association (CMA) Award for Vocal Event of the Year. It was also honored with two awards from the Academy of Country Music. What makes the song stand out as one of the best ever is the relatability. Any working person has felt the same way Jackson does when he kicks the song off, singing, “The sun is hot and that old clock is movin’ slow / and so am I / Workday passes like molasses in the wintertime, yeah, but it’s July.” Every lyric hits home for an overworked and underpaid individual, culminating with the brilliant chorus: “Pour me somethin’ tall and strong / Make it a hurricane before I go insane / It’s only half past 12, but I don’t care / It’s five o’clock somewhere.” This song became a mantra for people. And I can’t imagine a better ode to Buffett than to bring him in at the end, when Jackson sings about possibly going back to work for the day, but contemplates, “What would Jimmy Buffett do?” Which, we all know, he’s going to pick the good time. Sure, we can’t always live out this song, but we can sing along and dream about it being “five o’clock somewhere.” AHS

72. "The Next Episode" by Dr. Dre feat. Snoop Dogg, Nate Dogg and Kurupt (2000)
Album: 2001
Songwriters: Andre Young, Calvin Broadus, Melvin Bradford, David Axelrod, Brian Bailey & David McCallum

When a song has one memorable thing about it, usually it’s a good song. When it has two memorable things, it’s a hit. When a song has three or more memorable things, it’s iconic. Iconic is the only word needed to describe “The Next Episode.” Intro, video, hook, lyrics are all things you think of instantly when you think of this song. If someone says the next episode, I instantly hear “da da da da da”. This song also featured three legendary artists at the prime of their careers, which never hurts. ‘TNE’ also has crossover appeal with other fans who may not be hardcore hip-hop listeners. I’ve heard this song played at multiple sporting events. This song's appeal across various types of entertainment makes it one of the most essential hip-hop songs in history. CB

71. "Love Yourself" by Justin Bieber
Album: Purpose
Songwriters: Justin Bieber, Benjamin Levin & Ed Sheeran

The first time I heard "Love Yourself" by Justin Bieber, it instantaneously became my favorite song in his entire discography. Like many fans around the world, I had Bieber fever from the moment I first heard his breakout hit, "Baby." However, this song felt more mature and discusses many of the complex emotions that result from a breakup. Bieber realizes that he must have been so caught up in his job that he did not realize what was right in front of his face the whole time. It is a song with lyrics that bluntly tell this ex what he has been thinking about them. The most savage lyric is "My mama don't like you and she likes everyone." Bieber is telling this ex that they need to just love themselves because that is what they ultimately do anyway. "Love Yourself" was nominated for two Grammy Awards: Song of the Year and Best Pop Solo Performance. It went to No. 1 on the Billboard Hot 100, replacing another Justin Bieber song, "Sorry!" He was only the twelfth artist in Billboard history to accomplish this feat. While there was no denying the superstardom of Bieber at a young age, "Love Yourself" was such a refreshing song for him. Some stars who become famous at a young age struggle to make the transition from child stars to mainstream pop stars with lasting success. This song proved that Justin Bieber was going to have no trouble at all with that transition. "Love Yourself" proved that Bieber is here to stay. TG

70. "The Cave" by Mumford & Sons (2010)
Album: Sigh No More
Songwriters: Mumford & Sons

Mumford & Sons emerged out of nowhere in late 2009 with their folk-rock album Sigh No More, which brought a stripped-down, “we actually play instruments” vibe back into popular music. “The Cave,” the third single off that debut album, is my favorite release of their career. Do you know how awesome it is to hear banjo as a primary instrument in a hit pop song? The lyrics to the song are rather dark, but there’s such a foot-stomping, anthemic feel to the music you can’t help but belt it at the top of your lungs like it’s filled with happiness. JS

69. "Ho Hey" by The Lumineers (2012)
Album: The Lumineers
Songwriters: Wesley Schultz & Jeremiah Fraites

In their heyday, the Lumineers were often likened to the “American Mumford & Sons,” and they undoubtedly rode a wave made popular in the U.S. and worldwide by their British counterparts. But to be perfectly honest, I’ve always enjoyed The Lumineers' discography more than that of Mumford & Sons. The Lumineers’ stardom began with 2012’s “Ho Hey,” off their self-titled debut album, which started as a kiss-off to disinterested audience members at their shows. Wesley Schultz told American Songwriter: “The song was an effort to get under people’s skin at shows in Brooklyn, where everyone is pretty indifferent. And I figured if we could punctuate it with shouts, we might get someone’s attention.” It might be the shouts of “ho hey” that draw your attention, but the story in the verses in between of a songwriter struggling to hold it down in a life of hardships is what immediately won me over. JS

68. "Stay With Me" by Sam Smith (2014)
Album: In the Lonely Hour
Songwriters: Sam Smith, James Napier, William Phillips, Tom Petty & Jeff Lynne

“Stay With Me” by Sam Smith is a song about heartbreak that truly lingers with you forever. In this crazy life we are living, the main thing we seek is human connection. We all want to be loved, seen and heard. In 2014, this song became a breakout hit for rising British pop star Sam Smith. They said that they wrote this song about the morning after a hookup. The fling is putting on their clothes and leaving, but sometimes all you want is for that person to stay. You are not even in love with them per se. You want that connection to last a little longer. This song really connected with music lovers everywhere. It went on to win Record and Song of the Year at the Grammys. Smith said when they won, “I want to thank the man who this record is about who I fell in love with last year. Thank you so much for breaking my heart because you got me four Grammys.” TG

67. "Yeah!" by Usher feat. Lil Jon & Ludacris (2004)
Album: Confessions
Songwriters: Jonathan Smith, Christopher Bridges, Sean Garrett, Patrick Smith, James Phillips, LaMarquis Jefferson & Robert McDowell

If you were to teleport to 2004 and tell my 16-year-old self that you don’t like the song “Yeah!” by Usher, I might judge you. And argue with you. And I’ll even argue today that it’s one of the best hip-hop songs for my millennial generation. Or label it “crunk&B,” according to Lil Jon, mixing both crunk and R&B. Released in 2004 off of his Confessions album, the song features Lil Jon and Ludacris. It was written by a team: Jonathan Smith, Christopher Bridges, Sean Garrett, Patrick Smith, Robert McDowell, James Phillips and LaMarquis Jefferson. “Yeah!” became the longest-running No. 1 single on the Billboard Hot 100 chart in 2004, spending 12 weeks on top. The song is about a man spotting a “shorty” at the club who seems familiar, only to find out she was best friends with his girl. But no matter, she’s soon “up on” him, screamin’ “Yeah.” Probably not great for his girl, but the song sure is catchy. While I wasn’t exactly “up in the club with my homies” as a teenager, the beat combined with the raging hormones made the chorus lines, “Next thing I knew / she was all up on my scream’ / Yeah, yeah, yeah, yeah, yeah, yeah” (and another six yeah’s) a total banger to sing along to. My generation is programmed to know this song by the first “Peace up, A-Town down” and the “synth riff” that kicks the song off. The song is completed with Luda and Lil Jon’s killer verses, which are, yes, crass. However, no matter what, it remains one of the best from the past 25 years. AHS

66. "I Saw God Today" by George Strait (2008)
Album: Troubadour
Songwriters: Rodney Clawson, Monty Criswell & Wade Kirby

George Strait will always be country music royalty. Whether he’s singing about heartbreak, real life or love, he’s doing it with a smooth Southern drawl and amazing lyrics, even if he didn’t actually write the songs. And that ear for a good song never faltered throughout his long career beginning in the early 1980s. He released “I Saw God Today” in 2008, the second single off his phenomenal Troubadour album. Written by Rodney Clawson, Monty Criswell and Wade Kirby, the song follows a man taking a walk while waiting for his wife to have their baby. Don’t read too much into that – the man has been “by her side for 18 hours straight,” it explains, so it’s not like he’s just willy-nilly taking a stroll while his wife is in active labor. Instead, it’s a sweet ballad about a man recognizing God in the everyday things of life – a flower growing up through the sidewalk, a couple expecting a child of their own and then, of course, seeing his beautiful miracle of a daughter for the first time. It’s a simple song of faith that anyone who believes in God can relate to. The chorus lines, “I’ve been to church, I’ve read the book, I know he’s here but I don’t look / Near as often as I should / Yeah, I know I should / His fingerprints are everywhere / I just look down to stop and stare / Opened my eyes and man I swear / I saw God today.” The song has always taken on a more profound significance for me, knowing that Strait’s only daughter, Jenifer, was killed in a car accident at 13. So, when he sings lyrics like, “Got my face pressed up against the nursery glass / She’s sleeping like a rock / My name on her wrist / Wearing tiny pink socks,” it makes the song a bittersweet testament to his personal faith. It goes beyond just a beautiful song, but one that you believe he believes. That makes it so much more powerful and important in his legendary discography. AHS

65. "Falling Slowly" by Glen Hansard & Marketa Irglova (2006)
Album: Once
Songwriters: Glen Hansard & Marketa Irglova

One of four Academy Award Best Original Song winners on this list, “Falling Slowly,” the collaboration between singer-songwriters Glen Hansard and Marketa Irglova for director John Carney’s 2007 romantic-musical drama “Once,” is one of the most beautiful songs and performances of the last 25 years. Hansard and Irglova, who performed at the time as the duo The Swell Season, essentially played themselves in the film, and their creation of “Falling Slowly,” is one of the most beautiful musical scenes in film history. Irglova would say in an Oscars acceptance speech: “This song was written from a perspective of hope, and hope at the end of the day connects us all, no matter how different we are.” You can hear the hopefulness bursting forth in the beautiful crescendo of the song. JS

64. "Leave the Door Open" by Silk Sonic (2021)
Album: An Evening with Silk Sonic
Songwriters: Bruno Mars, Brandon Anderson, Dernst Emile II & Christopher Brody Brown

Bruno Mars is one of the most exciting artists of this generation. His retro style has the unique ability to transfer you back to the peak of soul music in the ‘60s and ‘70s while also feeling fresh, new and current. His music is timeless. His versatility and powerhouse vocals have garnered him many fans, young and old. In 2021, Mars partnered with Anderson .Paak to form the superduo Silk Sonic. “Leave The Door Open” was their debut single, and it was met with massive critical acclaim and commercial success. It hit No. 1 on the Billboard Hot 100 in its sixth week. The song depicts a man at his house, ready for his lover to join him, but they are not coming. Silk Sonic sings that they will leave the door open, hoping she will change her mind and come over. The song went on to a surprise win for Record and Song of the Year at the Grammys, upsetting presumed frontrunners Billie Eilish and Olivia Rodrigo. TG

63. "Stick Season" by Noah Kahan (2022)
Album: Stick Season
Songwriters: Noah Kahan

I was a little late to the Noah Kahan train. But when I first heard “Paul Revere” off the extended We’ll All Be Here Forever version of his 2022 album Stick Season on my husband’s playlist while driving one day, I remember asking, “Who is this?” From there, the rest of that album earwormed its way into my mind. I was completely drawn to his folk-emo-pop vibe. I don’t know if it’s the state of the world or his beautiful, heartbreaking lyrics, but his music just speaks to me. I was a big fan of ‘Revere’ and “Dial Drunk” before I fully understood the mastery of the title track, “Stick Season.” At its surface, it’s a song about lost love. But it’s rich with descriptions of anger, fear and longing in a way that’s deeper than normal smash hits go. You mix those haunting lines with his voice that catches at certain points in the incredibly catchy chorus and it’s just gold: “And I love Vermont, but it’s the season of the sticks / And I saw your mom, she forgot that I existed / And it’s half my fault, but I just like to play the victim / I’ll drink alcohol ’til my friends come home for Christmas / And I’ll dream each night of some version of you / That I might not have, but I did not lose / Now you’re tire tracks and one pair of shoes / And I’m split in half, but that’ll have to do.” You don’t have to be in Vermont to get “season of the sticks,” because everyone experiences this season, metaphorically at least, in their life. AHS

62. "The Story" by Brandi Carlile (2007)
Album: The Story
Songwriters: Phil Hanseroth

I knew there would be a Brandi Carlile song on this list – but I think I surprised myself in going with what’s probably considered her breakthrough song, 2007’s “The Story,” instead of something like “The Joke,” “The Mother” or “Right On Time,” all released after I’d become a fan and helped me to become a fan. But “The Story,” is such an important song in the history of Carlile that I couldn’t help but settle on it. The song is one of the few in her repertoire that she didn’t have a hand in writing; it was written by her guitarist Phil Hanseroth and played by him and his brother Tim, also in Carlile’s band, before they even met and began collaborating with Carlile. But the intensity Carlile infuses into these wonderfully cathartic lyrics from Hanseroth gives the song an authenticity that makes it sound like she’s baring her soul – and, though they weren’t her words initially, they’ve become hers throughout two decades of incredible performances. JS

61. "Tennessee Whiskey" by Chris Stapleton (2015)
Album: Traveller
Songwriters: Dean Dillon & Linda Hargrove

Chris Stapleton has had such an incredible career that I almost hate to select a cover song for his selection on this list of the greatest songs of the last quarter-century, especially when he’s written so many fantastic songs himself. But his cover of “Tennessee Whiskey,” written by Dean Dillon and Linda Hargrove, and taken to No. 2 on the Hot Country singles chart in 1983 by George Jones, is both what put Stapleton on the stage as a grand performer and is probably his most beloved song. Stapleton takes the already terrific song about a man who compares his love to that of a fine-tasting whiskey and ups the sexiness of it with his silky-smooth vocals that show Stapleton would’ve been one of music’s finest crooners no matter what genre he performed. JS

60. "Ocean Eyes" by Billie Eilish (2015)
Album: Non-Album Single
Songwriters: Finneas O'Connell

Billie Eilish burst upon the music scene seemingly out of nowhere, and in a big way, in 2019 with her studio debut When We All Fall Asleep, Where Do We Go?. The album and its single “Bad Guy” would make her the second artist ever to sweep the big four Grammy Awards (Album, Record, Song and Best New Artist) in the same year. However, it was her debut single, “Ocean Eyes,” which was first released on Soundcloud in late 2015 and commercially in 2016, that I still consider her greatest work to this day. Written by her brother and producer, Finneas O’Connell, “Ocean Eyes” was recorded by Eilish when she was just 13 years old. It’s amazing someone so young could capture the essence of falling in love with someone, and the vocals and production make “Ocean Eyes” an essential piece of dream-pop. JS

59. "Take a Bow" by Rihanna (2008)
Album: Good Girl Gone Bad: Reloaded
Songwriters: Mikkel S. Eriksen, Tor Erik Hermansen & Shaffer Smith

When people are cheating on their partner, most of the time, they do not want to leave the relationship they are in. They just want to “have some fun” on the side, but want to hide that part of them as if it does not exist. They pretend to be a good person, and in some cases, they give Oscar-worthy performances. That’s the subject that Rihanna’s “Take A Bow” takes. Rihanna tells her lover to take a bow to his standing ovation, but the curtain is finally falling. Using the imagery of a theater performance to allude to a man giving a performance in their relationship was genius. It seems the public agreed. “Take A Bow” was the first single released on Rihanna’s third studio album, Good Girl Gone Bad: Reloaded. It became Rihanna’s third No. 1 on the Billboard Hot 100. This song resonates with anyone who has ever felt like a fool for trusting someone they loved. It's unfortunate that it's been eight years since Rihanna released new music. However, it is great to know that we have gems like this in the world that continue to resonate for years after their release. TG

58. "Before He Cheats" by Carrie Underwood (2006)
Album: Some Hearts
Songwriters: Josh Kear and Chris Tompkins

The hit TV reality competition series, “American Idol” has been around for years. While there have been many winners that got record deals, most of their careers have not really taken off the way they probably expected. There are two exceptions to that rule: Kelly Clarkson (who has already appeared on this list) and Carrie Underwood. Underwood is arguably the most popular winner of “American Idol.” Underwood’s debut album, Some Hearts, produced hit after hit. The biggest one, though, was her fourth single, “Before He Cheats.” It became the first ever country song to sell over two million digitally and was once THE best-selling country song of all time. The song is really a revenge fantasy anthem for anyone who has been cheated on. In the song, Underwood is a woman who has just found out that her partner was unfaithful and has decided to take a Louisville slugger to his car in retaliation. While most people aren’t going to literally do this, it does feel like therapy in a way to listen to this song. “Before He Cheats” won the Grammy Award for Best Female Country Vocal Performance and Best Country Song. It even contended in the general field category of Best Song of the Year. TG

57. "Colors" by Black Pumas (2019)
Album: Black Pumas
Songwriter: Eric Burton

Rarely does a song from an artist I’ve never heard of knock me off my feet like “Colors” by Black Pumas did in 2019. Everything about the song – the vocals and lyrics by Eric Burton and the musicianship and production by guitarist/producer Adrian Quesada – just oozed joy. It was a song inspired by multicolored tones in the sky in Alamagoro, N.M., where Burton had just woken from a nap atop his uncle’s home. The song has a throwback sound, a blend of soul, R&B, blues, and gospel, which makes for an uplifting pop track. It was the kind of sound we needed around its release – and quite possibly need even more right now. Black Pumas were nominated for Record of the Year at the 2021 Grammy Awards for “Colors.” JS

56. "Ms. Jackson" by Outkast (2000)
Album: Stankonia
Songwriters: Andre Benjamin, Antwan Patton & David Sheats

If this song were made in any other era of hip-hop, you could legitimately say it had a case for being the best hip-hop song ever. This is how tough this era of hip hop was. “Ms. Jackson” was a classic for many reasons, but the hook(chorus) of the song is what makes it stand out. Andre 3000 and Big Boi are both great as solo artists, but in my opinion, this is their best work. I remember first listening to this song during the Ice Storm we had in December of 2000. It was rumored that the name “Ms. Jackson” was chosen as the title for this song because it is a common name and can be related to personal situations in life. This is yet another reason why this song and this specific era of hip hop were special. These songs actually had meaning and told stories rather than just having a catchy beat. Currently, it seems as though Andre 3000 and Big Boi are enjoying themselves as solo artists, which is understandable given the talent level of both. Regardless of whether these artists create another Outkast album or continue down their own path, "Ms. Jackson" will always be a top hip-hop song. CB

55. "Cover Me Up" by Jason Isbell (2013)
Album: Southeastern
Songwriter: Jason Isbell

Jason Isbell was already known to some of us before 2013’s excellent Southeastern, but it was that album that truly marked his breakthrough point for many who would come to call him one of their favorites. The standout on that album is “Cover Me Up,” a super emotional and vulnerable ballad, inspired by his then-wife, Amanda Shires, who truly helped save his life by being the impetus for him going into alcohol rehab and kicking a demon that had taken over his life. The vulnerability of loving somebody enough to break out of such a hold on your life comes through perfectly in the stripped-down song that is probably the best vocal of Isbell’s career. JS

54. "Summer's End" by John Prine (2018)
Album: The Tree of Forgiveness
Songwriter: John Prine & Pat McLaughlin

John Prine was one of the greatest singer-songwriters who ever lived. He had everything you could want from a songwriter – story songs that could tear you apart, witty, humorous songs that could both make you laugh and think, and just a supreme knack for saying things in ways seemingly no one else could. His self-titled debut album, released in 1971, is one of the greatest albums ever recorded. Due to the kind of music he recorded – he was essentially Americana long before the term was created – he was never a huge pop success with radio airplay, which led to him being a unheralded and underknown artist to many, but a songwriting hero to those within the industry or extended musical knowledge outside of the mainstream. Luckily, in the 2000s, there was a new interest in Prine’s music with singer-songwriters like Jason Isbell, Sturgill Simpson and Kacey Musgraves singing his praises and leading more and more fans to find his discography. This interest in his music led to his first album of original songs in over a decade, when he released The Tree of Forgiveness in 2018. The best song on that record was “Summer’s End,” which he penned with friend Pat McLaughlin, and told the heartbreaking story of someone who has been kicked down by life and found themselves away from the one’s they loved, and having a loved one reach out and let them know it’s OK to come on back. It’ll have you reaching for a box of tissues. Unfortunately, we lost Prine at age 73 in 2020, one of the many victims of the COVID-19 pandemic. His 2018 release showed there was so much more to look forward to from him. JS

53. "I Hope You Dance" by Lee Ann Womack (2000)
Album: I Hope You Dance
Songwriters: Mark D. Sanders & Tia Sillers

“I Hope You Dance” is one of the most universal songs ever written. The Grammy-winning hit appears to be from the perspective of a parent offering advice to their children about the world and how to approach it. However, it is advised that they need to be giving themselves as well. The truth is that this world is a very cruel place. Sometimes, the bad guy wins, you don’t get the person you love, you don’t end up being an Oscar-winning actor, and you may not be a pop superstar. This song is truly a song of hope. Womack sings, “I hope you never lose your sense of wonder” and “May you never take one single breath for granted.” The greatest moment, though, is going into the chorus that “when you get the chance to sit it out or dance, I hope you dance!” Womack wants us to fully embrace living, take risks, pursue our dreams, and smile and dance through all the good and the bad. “I Hope You Dance” has become Womack’s signature song. It won the Grammy for Best Country Song and the Country Music Association (CMA) Single of the Year. It is truly a timeless song that will matter to people in 3000 just as much as it did in 2000. TG

52. "Lose Yourself" by Eminem (2002)
Album: 8 Mile
Songwriters: Marshall Mathers, Jeff Bass & Luis Resto

At the 2003 Academy Awards, I was a big supporter of the blockbuster musical, “Chicago.” That night, “Chicago” won six Academy Awards, including Best Picture. One of the categories it was up for was Best Original Song for “I Move On.” It was the song I was rooting for to win the category. When the envelope was opened, it was a shocking upset that Eminem’s “Lose Yourself” from his film, “8 Mile” had claimed the top prize. It was the first rap song to ever win this category. Despite its commercial success and award nominations, few industry experts expected it to win the Oscar. After winning, I listened to the song as many do out of curiosity. What was this song that had managed to do something that had never been done before in Academy Award history? As someone who has always been a dreamer, I grew to love the song so much. The lyrics that really resonated with me is “You only get one shot. Do not miss your chance to blow. This opportunity comes once in a lifetime.” I am someone who doesn't listen to rap in my everyday life, and this song managed to break through to my list of Liked Songs on Spotify. “Lose Yourself” also became the very first rap song to be nominated in the Best Song category at the Grammys. This history-making rap song’s crossover appeal makes it an essential entry on this list. TG

51. "The World is On Fire" by American Aquarium (2018)
Album: Things Change
Songwriter: BJ Barham

At this point, there have been plenty of songs written about the questionable moral direction of the United States thanks to the Trump presidency. But in the middle of the president’s first term in 2018, alternative country/rock band American Aquarium released “The World Is on Fire,” and it really resonated with those disillusioned by what was happening. The song, featured on their album Things Change, was written by the group’s brilliant band leader, BJ Barham, who began writing it the night after Trump’s 2016 election. According to an interview with American Songwriter, Barham finished it in 2017 when he found out his wife was pregnant, which moved the song from hate to hope, he explained. This perspective solidified the song's longevity and moving nature. It perfectly captures anger and confusion, focusing first on a couple discussing what the world is coming to and how there were no words to convey the hurt. It then moves into deeper reflection, with powerful lyrics like, “When did The Land of the Free become The Home of the Afraid?” and Barham’s demanding tone on the lines, “This ain’t the country my grandfather fought for / But I still see the hate he fought against.” The last verse encapsulates hope for the future, focusing on his “baby girl comin’ in the spring,” and how if “anyone builds a wall in her journey / Baby, bust right through it.” The chorus is also hopeful, recognizing that the “load is heavy and the road is long,” but we must “be the light.” It was a song I had on repeat for a long time after it was released. And it’s one I’ve gone back to when politics start to erode morality because it lets me express my frustration, while tapping into hope for the future. It’s one of the best songs ever written for this time in history. AHS

50. "Heaven Sent" by Parker Millsap (2016)
Album: The Very Last Day
Songwriter: Parker Millsap

It’s always fascinating to me how a songwriter can put themselves in someone else’s shoes – someone who isn’t like them – and create a story of such empathy and grace. One of my favorite examples of this is “Heaven Sent,” from Americana singer-songwriter Parker Millsap. He puts himself in the shoes of a gay son of a preacher who is wondering why his father can’t seem to love the person he is, despite telling him all of those years how Jesus loves everyone. Millsap’s vocals wring every bit of the pain and hurt felt by his narrator, to the point that it’s almost surprising it’s a song from a fictional point of view. It’s a mesmerizing, heartbreaking and thought-provoking song. JS

49. "Shallow" by Lady Gaga & Bradley Cooper (2018)
Album: A Star Is Born
Songwriters: Lady Gaga, Andrew Wyatt, Anthony Rossomando & Mark Ronson

Lady Gaga had acted in the FX series, “American Horror Story: Hotel.” She had even won a Golden Globe for the role. However, the Hollywood Foreign Press Association had started to develop a reputation for being overly fond of stars and celebrities, rather than focusing on the actual work when deciding winners. That is why Gaga’s win wasn’t widely respected. This was even more evident when Gaga failed to even be nominated in the same category for the Primetime Emmy Awards. However, when Bradley Cooper’s remake of “A Star Is Born” came out, it was clear that Gaga was a star. Gaga received her first Oscar nomination for Best Actress for “A Star Is Born.” She was also nominated for Best Original Song for writing the epic power ballad, “Shallow.” “Shallow” was a song that blew up everywhere. You would hear it on every radio station, it hit No. 1 on the Billboard Hot 100, it won the Golden Globe for Best Original Song and also won Lady Gaga her first Academy Award in the Best Original Song category. “Shallow” was even nominated for Record and Song of the Year at the Grammys, and it won the category for Best Pop Duo/Group Performance. This beautiful song reminds us that we are all seeking deep connections in this lifetime. We don’t want to be superficial or shallow in our relationships. We want our lives to mean something. This song really connected with movie and music lovers everywhere. TG

48. "Enchanted" by Taylor Swift (2010)
Album: Speak Now
Songwriter: Taylor Swift

You will notice that most of the songs that are on this list of the Best Songs of the 2000s were released as singles. They played in high rotation on the radio, topped the Billboard Hot 100, and were even nominated for and/or won Grammys. “Enchanted” by Taylor Swift is a rare entry on this list that did not achieve any of this. However, a list would not be complete without “Enchanted” on it. Swifties, her loyal fan base, made this song the song most associated with her third studio album, Speak Now. It is everything you could ever want from not only a Taylor Swift song, but from music in general. This beautiful, epic power ballad that journeys into country, rock and pop documents that moment in life where we see someone for the first time. Our heart begins to flutter and we almost instantaneously are smitten. We find it difficult to breathe being in their presence. We begin to fantasize about that person and start hoping that they are not romantically involved with anyone because we are hoping for a future with this person. At The Eras Tour, one of my favorite moments was screaming the bridge to this song along with 65,000 other Swifties. I was telling the one I loved to “Please don’t be in love with someone else!” “Enchanted” is a song that truly captures the magic of falling in love with someone at first sight. No other song comes close. TG

47. "Zip City" by Drive-By Truckers (2001)
Album: Southern Rock Opera
Songwriter: Mike Cooley

The Drive-By Truckers, primarily songwriters Mike Cooley and Patterson Hood, are perhaps the best group at crafting songs about less-than-stellar members of society, while making you feel their point of view by truly getting into the minds of these characters. I like to refer to much of their best works as “greasy and sleazy,” and nothing represents that better than Cooley’s “Zip City,” off 2001’s Southern Rock Opera. The song, which features the band’s epic dueling guitars of Cooley and Hood, is from the point of view of a Southern teenage boy who doesn’t have many interests other than getting laid and having been a teenage boy in the South – though certainly not like this one – I’ve seen first-hand through classmates how well Cooley knows this character. JS

46. "DNA" by Kendrick Lamar (2017)
Album: Damn
Songwriters: Kendrick Duckworth & Michael Williams II

You can make a case for other songs, such as “Humble” or even “Not Like Us,” to be included on this list, but “DNA” is our Kendrick Lamar selection. True hip hop songs are coded with a story, and I think the meaning behind this song, being the frustration Black people feel due to racism, is too important to pass up for a list such as this. This song is significant due to its role in combating racism and advocating for one's beliefs, even if it's not the ideal outcome. Lamar was already an established artist, but this song took him to another level, as it was used for promotional items for the NBA and TV shows, among other things. Songs that are relatable to true hip hop fans but have the ability to crossover usually can stand the test of time. If Lamar continues on his current path, we could look at this song being even more important a few years down the road. CB

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45. "7 & 7" by Turnpike Troubadours (2010)
Album: Diamonds & Gasoline
Songwriters: Evan Felker

Turnpike Troubadours was one of those bands that I thought was my little secret for a while, around 2012 when they released their second album, Goodbye Normal Street, and I heard them on a local radio station that used to play “red dirt country music.” I loved that album, as well as their previous one, Diamonds & Gasoline. When I saw them live at a small club show in Little Rock, I was impressed by the intensity with which they performed on stage; they instantly became one of my favorite bands. They’re no longer a secret – they now play packed arenas - but are still somewhat under the radar because they play actual country music in an era when country mainstream has gone to a more pop or bad rock sound. “7&7,” off Diamonds & Gasoline, has always been my favorite Turnpike song. It has an infectious, rebellious spirit to it of a kid who never completely grew up, and still affectionately looks back at running around with a girl, who moved on when he never did. The chorus: “I had no clue/I’d be the boy who/your mama warned you about” is one I’ve always loved scream-singing, whether at a live show or just in my car via Spotify. JS

44. "Small Town Southern Man" by Alan Jackson (2007)
Album: Good Time
Songwriter: Alan Jackson

Alan Jackson seemed to understand the life of a Southern man better than most country music stars of his era. I’m sure it came naturally to him, as a Georgia-born and bred son to a Southern man and family. “Small Town Southern Man” is one of my all-time favorite Jackson songs, and one I believe to be underrated among his discography. It was inspired by Jackson’s father and grandfather and Georgian ancestry, in general, with some lines closer to home than others, like the truthful: “First there came four pretty daughters for the Small Town Southern Man, then a few years later came another, a boy, he wasn’t planned.” Jackson told Country Weekly: “Wherever you go, there are rural people that are working for a living and raising families. They all have the same qualities and goals as a small-town Southern man.” Perhaps this is why this song has always reminded me of my own father, a Georgia-born and bred Southern man himself. “Small Town Southern Man” was Jackson’s 23rd No. 1 country hit of his career. JS

43. "Oops! ... I Did It Again" by Britney Spears (2000)
Album: Oops! ... I Did It Again
Songwriters: Max Martin & Rami Yacoub

Growing up in the rural South, I listened to mostly country music: George Strait, Reba McEntire, Dolly Parton, and Garth Brooks, to name a few. I did not listen to pop music at all. This all stopped immediately when pop superstar Britney Spears walked onto the scene. I remember my cousin and I making up a dance to her song, “Sometimes,” from her debut album. My absolute favorite song of her entire career, thus far, is her hit song “Oops! ...I Did It Again.” The titular song of Spears’ second studio album told audiences and critics everywhere that she was here to stay. The iconic music video remains one of the best of all time. The song was nominated for Best Female Pop Vocal Performance at the Grammys, but surprisingly, it only reached No. 9 on the Billboard Hot 100. “Oops! ... I Did It Again” remains to this day a song that, if it ever comes on the radio or a Spotify playlist, it simply cannot be skipped. In the song, Spears is singing about flirting with a guy who mistakes her intentions as more serious. She does not want anything serious, but he is ready for a relationship. She is apologizing for messing with his heart. This song will always represent a highlight from an iconic pop superstar. TG

42. "Troubadour" by George Strait (2008)
Album: Troubadour
Songwriters: Leslie Satcher & Monty Holmes

George Strait had already had one of the greatest careers in the history of country music by 2008, to the point where he’d already had the nickname “King George” for quite a while, which is truly saying something since George Jones was one of the icons of the genre. “Troubadour,” the second single off the album of the same name (also the second single from that album on this list), was the perfect summation of his, at that time, already more than a quarter-century-old career. Despite being written by Leslie Satcher and Monty Holmes, a lyric like: “I was a young troubadour when I rode in on a song/And I’ll be an old troubadour when I’m gone.” “Troubadour” felt like a nice bow on Strait’s career, and though he’s still recording new music nearly 20 years later, it still feels like the one song most representative of it. JS

41. "Fallin'" by Alicia Keys (2001)
Album: Songs in A Minor
Songwriter: Alicia Keys

In 2001, I was completely obsessed with soap operas. One afternoon, I recall a promo that came on, showcasing the drama that would unfold in the coming week. The song being used in the background was one I had never heard before, but I was instantly hooked. I remember going to my computer and typing in the lyrics to look up the song that had just played. I discovered this song was called “Fallin’” by newcomer Alicia Keys. This was a testament to how music being used for promotions can benefit the artist. I became a fan of Alicia Keys that day. “Fallin’” is such a soulful R&B song that really captures that feeling of being so head over heels in love with someone one day, and then the next, you fall out of love with them just as hard – the same level of intensity. It captures the tumultuous nature of first love perfectly. “Fallin’” was a hit critically and commercially. It went No. 1 on the Billboard Hot 100 in its eighth week for six non-consecutive weeks. The song would go on to win three Grammys: Song of the Year, Female R&B Vocal Performance and Best R&B Song. It was also nominated for Record of the Year but lost to U2’s “Walk On.” TG

40. "Alexander Hamilton" by Original Broadway Cast of "Hamilton"
Album: Hamilton (Original Broadway Cast Recording)
Songwriter: Lin-Manuel Miranda

Sometimes songs just feel right – they fit with the times culturally, maybe to kick off a movie or in that earworm way where you know you’ll never forget it. And then, on top of that, there’s perfection. The song, “Alexander Hamilton,” is both. It’s the opening number of the 2015 phenomenon Broadway musical “Alexander Hamilton.” The musical changed Broadway, changed people’s relationship to theater and what it could be, and solidified the genius of Lin-Manuel Miranda, who wrote and performed in it. ‘Hamilton’ sets up the musical perfectly, encapsulating the tragic upbringing of founding father Alexander Hamilton while introducing the characters who will shape his life. Lasting just three minutes and 56 seconds, it’s a masterclass in storytelling, balanced with the challenge of setting up the whole production. It sets the mood from the first drum beats to the opening delivered by rival Aaron Burr (Leslie Odom Jr.): “How does a bastard, orphan, son of a whore and a Scotsman, dropped in the middle of a forgotten spot in the Caribbean by providence, impoverished, in squalor grow up to be a hero and a scholar?” There are numerous standout songs in this musical that awaken a love of history in young people by telling the story through people of color and incorporating rap and hip-hop. Its influence and impact outweigh any critical voices 10 years later. And this song will always be seared into my brain as one of the best ever written, even beyond the musical itself. AHS

39. "Bye Bye Bye" by NSYNC (2000)
Album: No Strings Attached
Songwriters: Kristian Lundin, Jake Schulze & Andreas Carlsson

“Bye Bye Bye” by NSYNC was released just two weeks into 2000, but every time it comes on the radio, we say “hi, hi, hi” and dance like we did the very first time we heard it. I have been to many weddings and dance parties in my lifetime, and every time this song is played, people lose their minds. They could have been just sitting down having a conversation with the previous song, but when “Bye Bye Bye” comes on, it turns the dancing switch on for them. The song’s lasting legacy is undoubtedly due to the iconic music video, in which all the bandmates are puppets controlled by model Kim Smith. This song was so huge for NSYNC that it is crazy to think it only reached No. 4 on the Billboard Hot 100. “Bye Bye Bye” was so insanely popular that it was even nominated for Record of the Year at the Grammys, as well as Best Pop Duo/Group Performance with Vocals. “Bye Bye Bye” captures those moments of a crazy relationship where they know it is time to go, and they have had enough of the person. This anthem for saying good riddance to a horrible relationship still resonates more than 25 years later. TG

38. "The Cowboy in Me" by Tim McGraw (2001)
Album: Set This Circus Down
Songwriters: Al Anderson, Jeffrey Steele & Craig Wiseman

If one were to expect a Tim McGraw song to be on such a list as this, they would probably assume the choice to be his 2004 Grammy, Country Music Association and Academy of Country Music award-winning “Live Like You Were Dying.” That song is great, but also one that, through massive overplay, should also be retired. I’ve gone with more of a personal McGraw selection with his 2001 country No. 1 hit, “The Cowboy in Me,” written by Al Anderson, Craig Wiseman and Jeffrey Steeler. The lyrics to “The Cowboy in Me,” especially its chorus of: “The urge to run/the restlessness/the heart of stone/I sometimes get/the things I’ve done for foolish pride/the me that’s never satisfied/the face that’s in the mirror when I don’t like what I see/I guess that’s just the cowboy in me,” speak so much to me. They speak to one’s anxieties, especially from a man’s perspective, so perfectly that I couldn’t help identifying with them – and have from my teenage years to my late 30s. One doesn’t have to be a cowboy of the roping and riding variety to understand what McGraw means by “The Cowboy in Me.” JS

37. "A Little Bit of Everything" by Dawes (2011)
Album: Nothing is Wrong
Songwriters: Taylor Goldsmith

Taylor Goldsmith, the songwriter and vocalist for Los Angeles band Dawes, is one of the most literary songwriters around today, and, though his lyrics certainly have led to some criticisms of being pretentious, I’ve always simply viewed them as the works of a genius. His best composition, in my mind, is “A Little Bit of Everything,” off the group’s 2011 album Nothing is Wrong. The song focuses on the things in life – both major and minor – that can have a large impact on people in ways both tragic and joyful, and does so in a series of vignettes that remind us of real-life situations, like a man contemplating suicide and a woman preparing for her wedding. - JS

36. "The Pretender" by Foo Fighters (2007)
Album: Echoes, Silence, Patience & Grace
Songwriters: Dave Grohl, Taylor Hawkins, Nate Mendel & Chris Shiflett

I love good rock music. I wouldn’t consider myself a hard rock fan, and I generally don’t enjoy screaming unless it fits in well with a song. “The Pretender,” the first single off of Foo Fighters’ 2007 album Echoes, Silence, Patience & Grace, is a song where it fits beautifully. Written by the band’s founder and lead singer, Dave Grohl, the late Taylor Hawkins, Nate Mendel and Chris Shiflett, it’s one of the hardest songs that became a hit for the band. The song is an anthem against being manipulated and deceived. It’s something everyone can relate to. It starts with a low, haunting melody in the intro lines, “Keep you in the dark, you know they all pretend / Keep you in the dark and so it all began,” and then just takes off. It’s full throttle in the chorus and bridge, screaming things like “What if I say I will never surrender?” and “Yeah, who are you?” It’s a song you can listen to if you’re in a rock mood or need some catharsis. Grohl’s voice is the standout, holding up brilliantly in the quieter moments and intense angst. It’s one of Foo Fighters’ best. AHS

35. "The Weary Kind" by Ryan Bingham (2009)
Album: Crazy Heart: Original Motion Picture Soundtrack
Songwriters: Ryan Bingham & T Bone Burnett

I don’t think I could ever get away with saying Ryan Bingham’s “The Weary Kind” is the greatest Oscar-winner ever for Best Original Song, especially when “Over the Rainbow” from “The Wizard of Oz” is in existence … but it is my favorite. Give me a movie about a grizzled country singer struggling to make it in the modern world, and I’m going to be a happy man. Director Scott Cooper’s 2009 film “Crazy Heart,” featuring Jeff Bridges in such a role (one for which he won Best Actor), is one of my favorites of that specific type of movie. Bingham wrote “The Weary Kind,” along with T Bone Burnett, as the theme for Bridges’ “Bad” Blake, and it is a masterpiece of a downtrodden, hard-lived life on the road as a traveling musician. Bingham’s voice wrings every bit of emotion possible out of these words that’ll put you in “Bad” Blake’s shoes. JS

34. "Gold Digger" by Kanye West feat. Jamie Foxx (2005)
Album: Late Registration
Songwriters: Kanye West, Ray Charles & Renald Richard

Due to Kanye West’s behavior over the past few years, it was tough for me to include him on this list. I'm typically not the type of person who separates artists from their craft. If you are a shitty person, it's just easier not to deal at all. However, due to his contribution to this era of hip hop, it's hard to leave out Kanye West. Like Kendrick Lamar, I could've picked multiple songs (“Jesus Walks,” “Can't Tell Me Nothing,” “Amazing”) for this list. I picked “Gold Digger” due to its blend of old school sound with the sample of Ray Charles’ “I Got a Woman,” as well as the feature of Jamie Foxx. If you go back to this song, Foxx was already an established actor, thanks to his TV show and movies, such as his recent (at that time) Oscar-winning role as Charles in “Ray.” Up to this point, Foxx hadn’t reached superstar status as a music artist. This is a top song because it ushered in a new superstar in Foxx, and it also gave us a different sound for hip hop songs. Artists had used samples in other songs, but “Gold Digger” revolutionized that style of music. CB

33. "All of Me" by John Legend (2013)
Album: Love in the Future
Songwriters: John Legend & Toby Gad

“All of Me” is the first song that I ever heard from John Legend. My wife had heard this song and, knowing my adoration of love songs, she recommended it to me. After listening to it, I was hooked. Legend’s beautiful song for his wife touched me in ways music doesn’t do very much anymore. The line “All of me loves all of you” really signifies that this person loves everything about you – not just the things that are easy to love, but all of the complexities around that person as well. “All of Me” is so romantic that it almost feels like a song that should be in a romantic comedy where our expectations for what love can be can never be met. Legend’s love for his wife, Chrissy Teigen, made me realize that true love is possible in ways I had not considered before. The song was nominated for the Grammy for Best Pop Solo Performance in 2015 and became Legend’s first No. 1 on the Billboard Hot 100. It’s one of the most timeless love songs of the last quarter-century. TG

32. "Vice" by Miranda Lambert (2016)
Album: The Weight of These Wings
Songwriters: Miranda Lambert, Josh Osborne & Shane McAnally

Miranda Lambert has been my favorite female country artist pretty much since her 2005 debut single, “Kerosene.” Lambert has always had an edge and ear for picking or writing songs that just connect to her style. For a good period, she and her then-husband, Blake Shelton, were kind of the king and queen of country music, something she poked fun at on her Platinum album. So, when news of their divorce hit in 2015, I knew the next album would likely be both a breakup album and, even more, a cathartic, deeply introspective listening experience. And it came true in the form of The Weight of These Wings, a double album with 24 songs released in 2016 that ranked in 2020 as one of Rolling Stone’s 500 greatest albums of all time. “Vice” was the lead single, and it’s still one of her best in an impressive discography. Written by Lambert, Josh Osborne and Shane McAnally, the song kicks off with a crackling record player sound and haunting acapella lines from Lambert: “Sting of the needle dropping on a vinyl / Neon singer with a jukebox title full of heartbreak / 33, 45, 78 / When it hurts this good you gotta play it twice / Another vice.” Then come the drums and guitar, and we journey with Lambert talking about the vices of alcohol, sex and addiction to goodbye. It was her most raw song then (before “Tin Man”), and the listener can just hear the painful cut into her reputation that she’s acutely aware of, and how far she fell. Anyone who has hit rock bottom can relate to this song, and I came to respect her even more as an artist after this one for her vulnerability. This album was Lambert’s turning point, and “Vice” was the perfect song for that moment. AHS

31. "Big Pimpin'" by Jay-Z feat. UGK (2000)
Album: Vol. 3... Life and Times of S. Carter
Songwriters: Shawn Carter, Chad Butler, Bernard Freeman & Timothy Mosley

I am completely biased when it comes to this song because it is my favorite of all time, regardless of genre. “Big Pimpin’” by Jay-Z feat. UGK has everything you want in regard to an iconic song. The music video, beat, lyrics, features and cultural relevance are all at the top when it comes to this song. I mentioned in a previous paragraph that Lil’ Wayne had an Iconic run in the mid-2000s. The same can be said for Jay-Z. He had a run from the mid-90s that spanned over a decade, during which he dominated the music scene. Jay-Z by himself has plenty of hits, but once you add a group like UGK (Underground Kings), it can only enhance the song. Another thing that makes this song great is the blend of Jay-Z's East Coast style with UGK's Southern sound. Being from the South myself, I was familiar with UGK before they were mainstream. UGK is one of the best hip hop duos in history, and their verses on this song only add to that legacy. “Big Pimpin’” is one of those songs that was definitely a product of its time, and listening back to some of the lyrics, you can make the case that it aged poorly. With that being said, you can't deny the impact the song had on the careers of Jay-Z and UGK, as well as hip-hop overall. CB

30. "Merry Go 'Round" by Kacey Musgraves (2012)
Album: Same Trailer, Different Park
Songwriters: Kacey Musgraves, Josh Osborne & Shane McAnally

Few artists tell the truth about life in their debut single. Country music has the tagline, “Three chords and the truth,” but too often, the genre has centered on the cliche and surface level, like “country living” is all about beer, trucks and a Mayberry fantasy. When Kacey Musgraves burst onto the scene with “Merry Go’ Round,” she blew up this narrative. It was released in September 2012 as the lead single off of her debut album, Same Trailer Different Park. Written by Musgraves, Josh Osborne and Shane McAnally, the song talks about the realities of small town life that aren’t always picturesque: Forced upon religion, drug addiction, affairs, young pregnancy and being stuck. The song was shocking from the first lines: “If you ain’t got two kids by 21 / You’re probably gonna die alone / At least that’s what tradition told you / And it don’t matter if you don’t believe / Come Sunday mornin’, you best be there / In the front row like you’re supposed to.” From there, the song paints a heartbreaking snapshot of how people get trapped in generational cycles with the “same hurt in every heart / same trailer, different park.” The lines that always get me the most are, “Just like dust, we settle in this town / On this broken merry go ’round.” It’s an important song in country music history because it went places few commercially successful artists go. And people took notice — it won her the Grammy for Best Country Song. Coupled with her silky smooth country voice, it was the perfect song to establish that she wasn’t going to put out typical country music. And while she’s experimented with more pop sounds in recent years, she’s always going to have a place in country because of this song. AHS

29. "Wrecking Ball" by Bruce Springsteen (2012)
Album: Wrecking Ball
Songwriters: Bruce Springsteen

What began as a tribute to a concert and sports venue wound up an ode to defiance and tenacity. Bruce Springsteen wrote “Wrecking Ball” in 2009 as an ode to Giants Stadium in Rutherford, N.J., where the New York Giants football team played its home games, and Springsteen had performed many times, when it was set to close and be demolished. When it became the title track to his 2012 album, it served as a message to never back down and never give in, even when life throws troubles your way. The Hollywood Reporter called the album Springsteen’s “angriest yet,” as it included themes of poor, hard-working folks being taken advantage of by the rich – something that still rings true more than a decade later. JS

28. "Single Ladies (Put a Ring On It)" by Beyoncé (2008)
Album: I Am ... Sasha Fierce
Songwriters: Beyoncé Knowles, Christopher "Tricky" Stewart, Terius "The-Dream" Nash & Thaddis Harrell

This powerful song by superstar Beyoncé is an anthem for all single ladies who are tired of men and their unwillingness to commit to long-term, serious relationships. It is a song about women's empowerment, encouraging women to recognize their worth and not let a man make them feel less than in any way. Beyoncé knows her worth, and she is saying, “If you like it, you should have put a ring on it!” This song is one that, when mentioned, you almost immediately think of the iconic music video. The video was shot in black and white and has Beyoncé dancing with two other backup dancers. Millions have replicated the choreography in videos over the years, demonstrating its enduring appeal and impact on pop culture. The music video went on to win the MTV Video of the Year Award and the song went on to win the Grammy for Song of the Year. Even though Beyoncé has been widely successful for at least two decades, when her name is mentioned, tons of people immediately think of this iconic song from 2009. We like it, and we are putting it on this list! Oh, oh, oh!!!! TG

27. "Times Like These" by Foo Fighters (2003)
Album: One by One
Songwriters: Dave Grohl, Taylor Hawkins, Nate Mendel & Chris Shiflett

The Foo Fighters have been the ultimate rock band of the 2000s. No rock act has consistently put out as much and as good music as the Dave Grohl-fronted band during that time. “Times Like These,” off the group’s 2003 album One by One, is their best track of this quarter-century. “Times Like These” is an uplifting song about overcoming difficult times and moving into a new day. Grohl was inspired to write the lyrics when he “felt like I wasn’t entirely myself,” during a hiatus in the band’s recording of the album after an unsatisfying first recording session, and his uncertainty about the band's future. It’s the type of song you just want to belt at the top of your lungs, especially as a means of telling yourself everything is going to be OK. JS

26. "Blinding Lights" by The Weeknd (2019)
Album: After Hours
Songwriters: Abel Tesfaye, Ahmad Balshe, Jason Quenneville, Max Martin & Oscar Holter

“Blinding Lights” by The Weeknd is a song that has garnered universal acclaim from critics and topped the Billboard Hot 100 for four non-consecutive weeks. It became the song with the most weeks spent in the top five and top 10 and the first song to hold a spot in the top 10 for an entire year. On November 23, 2019, it was named as the chart's best-performing song of all time. This song feels like it was made in the 1980s, yet it also feels fresh and current. It tells the story of how this person is alone at night, and while they may be slightly impaired by alcohol, they are not stopping until they get to the person they are longing for. While it does have a dark undertone of driving while drunk or under the influence, it captures the way that we all long for and love people in desperate ways. We cannot live without them if we can’t have them in that moment. Before the Grammy nominations came out in 2021, it was widely believed that “Blinding Lights” would be nominated and win for Record and Song of the Year. And why not? It was THE SONG of the year. However, on Grammy nominations morning, it was NOT even nominated for the award it should have been winning. The injustice of this song persists, but some justice is found in its inclusion on this list of the best songs of the 2000s. TG

25. "Whiskey Lullaby" by Brad Paisley & Alison Krauss (2004)
Album: Mud on the Tires
Songwriters: Bill Anderson & Jon Randall

Throughout the history of country music, there have always been stunningly tragic ballads that would make listeners weep with sadness, and Brad Paisley and Alison Krauss’s collaboration on the Bill Anderson and Jon Randall-penned “Whiskey Lullaby” is certainly one of the greatest and most tragic examples of this. The ballad, which is just accompanied by an acoustic guitar and a dobro relying mostly on the beauty of the vocals, is the story of the painful separation of a couple, which first leads to a heartbroken man drinking himself to death, as told from Paisley’s perspective, and then the similar demise of a guilt-ridden woman, as told from Krauss’s perspective. “Whiskey Lullaby” would be the Country Music Association’s (CMA) Song of the Year for 2005. JS

24. "Lollipop" by Lil Wayne feat. Static Major (2008)
Album: Tha Carter III
Songwriters: Dwayne Carter, Stephen Garrett, Darius Harrison, Jim Jonsin & Rex Zamor

Lil Wayne had an eight-to-10-year stretch of music that was simply better than everyone else's in hip-hop. These were not only songs he released, but also songs on which he was featured. Most of the time during that stretch, if Wayne was featured on a song, he had the best verse, and the song was guaranteed to be a hit. The song “Lollipop,” released in 2008, was the epitome of that run. Sometimes songs are hits, and other times they are HITS! “Lollipop” was undoubtedly a HIT! Wayne had better songs lyrically during this time, but overall, this was the best. The music video was simple yet powerful and was also dedicated to Static Major, who died a few weeks before the song was released. As I mentioned, during this time, Lil Wayne was on one of the greatest runs in the history of hip-hop, and then he released this song, which topped the charts. This is equivalent to a great athlete in their prime delivering an all-time performance on the biggest stage. CB

23. "Boulevard of Broken Dreams" by Green Day (2004)
Album: American Idiot
Songwriters: Billie Joe Armstrong, Mike Dirnt & Tre Cool

One of the biggest albums since 2000 was, without a doubt, Green Day’s 2004 concept album (or punk rock opera, if you will), American Idiot, which told the story of a lower-middle-class adolescent named Jesus of Suburbia during the era of 9/11 and the Iraq War. Somehow this album lost the Grammy Album of the Year to a duets record by Ray Charles – the always timely Grammy Awards, ladies and gentlemen! The best track on American Idiot, “Boulevard of Broken Dreams,” is a perfect encapsulation of the disillusionment and distress felt by America’s youth during President George W. Bush’s first term. Its emo power ballad sound makes it a perfect number for a punk rock opera and theme for a loner trying to make it on their own. JS

22. "Springsteen" by Eric Church (2011)
Album: Chief
Songwriters: Eric Church, Jeff Hyde & Ryan Tyndell

“Funny how a melody sounds like a memory” is the key lyric in Eric Church’s 2011 No.1 country hit “Springsteen,” in how he captures so eloquently the feeling of how music has the ability to stir emotions and bring people back to certain places in their past simply by hearing a song. Church, who wrote the song with Jeff Hyde and Ryan Tyndell, initially had the idea from another artist’s song, reminding him of a girl from his past, but chose Bruce Springsteen to convey the message because he admired the legendary performer. I’ve never heard a song that so perfectly captures the nostalgia that music from an artist you love can evoke. JS

21. "Blank Space" by Taylor Swift (2014)
Album: 1989
Songwriters: Taylor Swift, Max Martin & Shellback

Good songwriters are observant, pulling tidbits out of the everyday realities of life and crafting lyrics that resonate. When that tidbit is criticism or even personal attacks, you either rise above the noise and ignore it or turn it into something creative. Great songwriters get creative, and Taylor Swift is a great songwriter. One of her best examples of this is 2014’s “Blank Space.” When Swift’s popularity was high, but not to the off-the-charts global stardom she has today, she released her fifth album, 1989, transitioning her country sound to a more pop one. It was a turning point in a career that’s had quite a bit of musical exploration. “Blank Space” was her second release following the forever catchy “Shake It Off.” Written by Swift and album producers Max Martin and Shellback, “Blank Space” centers on the caricature Swift’s critics made her out to be – a glamorous seductress who is a hot mess when it comes to relationships. The lyrics immediately play into the temptress satire, as the character meets a man and promises to show him “incredible things / magic, madness, heaven, sin.” It’s really an empowering song for her and every woman who has been judged because of their relationships in the way men never would. It’s a lyrical and musical earworm and holds one of the best lines she’s ever written: “‘Cause, darling, I'm a nightmare dressed like a daydream.” Songs like this really paved the path for her next album, Reputation, and solidified her talent for turning the noise into something magical. It was No. 1 on the Billboard Hot 100 chart for seven weeks and made Rolling Stone's 500 Greatest Songs of All Time list in 2024. It remains one of Swift’s best songs in a very impressive discography. AHS

20. "Uptown Funk" by Mark Ronson & Bruno Mars (2014)
Album: Uptown Special
Songwriters: Mark Ronson, Bruno Mars, Philip Lawrence & Jeff Bhasker

My husband and I got married in June of 2015. We are big music lovers, and we had already crafted a good wedding reception playlist. But then we heard “Uptown Funk,” which was released in November 2014, and we knew immediately that we’d add it to the set. The instant pop classic was written by producer Mark Ronson, Bruno Mars, Jeff Bhasker and Philip Lawrence. In my research, I discovered some copyright issues that necessitated adding more writers to the track, but I won’t bore you by listing more names. The sing-rapping style song was released on Ronson’s Uptown Special album. The song topped the Billboard Hot 100 for 14 consecutive weeks and topped charts in 19 countries. It’s a perfect song for Mars because of his insane charisma and the old-funk style he’s brought to a new generation. It’s incredibly catchy with its “doh-doh-doh’s” and “Girls hit your hallelujah (Woo)” lines, culminating with “’Cause uptown funk gon’ give it to you / Saturday night and we in the spot / Don’t believe me, just watch.” The perfect blend of rhythm, lyrics and fun makes for a cool pop song. Every time I hear it, I’m instantly in a better mood. AHS

19. "Where Were You (When the World Stopped Turning)" by Alan Jackson (2001)
Album: Drive
Songwriter: Alan Jackson

When 9/11 happened, two songs became the soundtrack for a grieving nation: “Where Were You (When the World Stopped Turning),” by Alan Jackson and “Courtesy of the Red, White and Blue (The Angry American)” by Toby Keith. Both spoke to the mood of America at the time, devastated and angry. Looking back, ‘Courtesy’ isn’t a song I find myself returning to, but ‘Where Were You’ forever preserves one of the saddest moments in U.S. history. Jackson wrote the song a little more than a month after the attacks, explaining he “didn’t want to write a patriotic song” or a “vengeful” one, but something to reflect on real people’s feelings. That makes it wildly different from Keith’s contribution to this moment. Jackson said at the time he woke up at 4 a.m. with some of the lyrics and melody, which I believe was divine intervention, truly a lightning-in-a-bottle gift. The lyrics “Where were you when the world stopped turnin’ / That September day?” will get me even today, because we all remember where we were. It takes you back to that time. Jackson goes on to poignantly describe different perspectives of the day, from sitting down to cry, huddling around TVs with strangers, being alone driving on the interstate, going out and buying a gun or one of my favorite lines, “Did you turn off that violent old movie you’re watchin’ and turn on ‘I Love Lucy’ reruns?” The chorus is the song’s most beautiful part, explaining that God gave us faith, hope and love, “and the greatest is love.” The song served as a reminder of our humanity, a gift from our Creator, during a horrific moment. It’s one of the greatest songs — not just in the country genre — ever written about a turning point in history. AHS

18. "Kerosene" by Miranda Lambert (2005)
Album: Kerosene
Songwriter: Miranda Lambert & Steve Earle

There are a few artists who, right out of the gate, release a song that will cement their career, or at least continue to be one of their best. Miranda Lambert’s single, “Kerosene,” one of three singles off her debut album of the same name, falls into that category. Written by Lambert (with co-writer credit also given to Steve Earle after the fact), it’s an edgy song that defined the music she’d make throughout her career. From electric guitar licks to the harmonica sounds, the song is a kickass tribute about love gone wrong. In the music video, she’s walking while draining a can of kerosene as she angrily sings about her cheating boyfriend. Some of the hardest-hitting lyrics are when she sings, “Forget your high society / I’m soakin’ it in kerosene / Light ’em up and watch them burn / Teach them what they need to learn, ha” with that “ha” packing a punch. And then, of course, her twangy voice bellowing the lyrics, “Now I don’t hate the one who left / You can’t hate someone who is dead” is pretty perfect. Lambert has always excelled with songs like this, and releasing this one early in her career was a bold move. She wouldn’t be a pop-country artist, but one that will dig a little deeper and go a little darker. It’s one of my favorite Lambert songs, and one that made me a forever fan of hers. It’s one of the most important songs of her career. It became her first top 20 hit, reaching No. 15 on the Hot Country Songs Chart, and she earned her first Grammy nomination for Best Female Country Vocal Performance. AHS

17. "When I Was Your Man" by Bruno Mars (2013)
Album: Unorthodox Jukebox
Songwriter: Bruno Mars, Philip Lawrence, Ari Levine & Andrew Wyatt

Bruno Mars is such a remarkable artist in that he feels like a throwback to soul, R&B and pop of the past but also feels so current. His music is simply timeless. Arguably, my favorite song from Bruno Mars is “When I Was Your Man.” It is such a self-reflective song of a man who has been reflecting on what he did wrong in a relationship. His girl is gone and all he has left to think about is what he could have done to keep her. He sings to us about all the things he should have done when he was blessed to have her in his life. “When I Was Your Man” went to No. 1 on the Billboard Hot 100 and was nominated for the Grammy Award for Best Pop Solo Performance. This song even inspired Miley Cyrus’ Grammy-winning “Flowers.” TG

16. "In Color" by Jamey Johnson (2008)
Album: That Lonesome Song
Songwriters: Jamey Johnson, Lee Thomas Miller & James Otto

Jamey Johnson was a breath of fresh air in 2008 with his traditional country music and terrific story songs, at a time when pop music was beginning to infiltrate the Nashville scene. His 2008 album, That Lonesome Song, will go down as one of the greatest country music albums of all time, in my opinion. My first moment with the album was its first single, “In Color,” a top-10 hit in early 2009. Johnson, who wrote the song with James Otto and Lee Thomas Miller, exquisitely tells the tale of a grandfather showing old photographs to his grandson, and remarking about living those moments “in color,” or in person, while remembering times – both grand and horrific – like his wedding and his time fighting in World War II. “In Color,” which won Song of the Year at both the Country Music Association Awards and the Academy of Country Music Awards, is exactly what country music is supposed to be – tales of real life. JS

15. "Bad Romance" by Lady Gaga (2009)
Album: The Fame Monster
Songwriters: Lady Gaga & Red One

Lady Gaga’s “Bad Romance” is one of those songs that has such an iconic music video that every time you hear the song, the images from the video instantaneously pop into your head. The video tells the story that Gaga is kidnapped by supermodels who drug her and sell her to the Russian mafia. The setting is a white bathhouse. The fashion, choreography, set design, and a hit song combined to make this video a winner of the MTV Award for Video of the Year. The song also performed well on the Billboard Hot 100, topping out at No. 2, which, in retrospect, is surprising that it never reached No. 1. However, the song did go on to win Best Female Pop Performance at the Grammy Awards. Also, while Gaga has been in the business for almost 20 years, “Bad Romance” is still one of the first songs you think of when you say her name. TG

14. "Wagon Wheel" by Old Crow Medicine Show (2004)
Album: O.C.M.S.
Songwriters: Bob Dylan & Ketch Secor

“Wagon Wheel” has one of the most fascinating backstories of any popular song. The song was initially partially written by Bob Dylan in 1973 during sessions for the soundtrack of director Sam Peckinpah’s movie “Pat Garrett & Billy the Kid.” It was just a chorus, left as an unfinished song, but wound up on a Dylan bootleg that ended up in the hands of Old Crow Medicine Show member Chris “Critter” Fuqua. Fuqua gave the bootleg to Ketch Secor, the primary songwriter for O.C.M.S., who wrote verses around the chorus and melody to Dylan’s old sketch. The combination of Secor’s verses with Dylan’s chorus wound up as an epic travelogue song describing a hitchhiking trip south along the eastern coast of the U.S. Old Crow Medicine Show’s version became sort of a cult hit among music listeners outside mainstream radio, with its combination of folk, bluegrass and alt-country. That version remains the ultimate one and would’ve found its spot on this list regardless of mainstream popularity, which the song found in 2013 when country singer Darius Rucker had a smash hit with it, and took it to both No. 1 on the Billboard country charts and a Grammy Award win for Best Country Solo Performance in 2014. JS

13. "Mr. Brightside" by The Killers (2003)
Album: Hot Fuss
Songwriters: Brandon Flowers & Dave Keuning

I’m genuinely shocked as I type this. I had no idea that 2003’s “Mr. Brightside” was the first release from the American rock band The Killers, off their debut album, Hot Fuss, released in 2004. It’s not unusual for a first song to catapult groups into stardom, but it’s a whole other dimension to have your first single be a generational anthem, as it’s been referred to for millennials. I’m also shocked that in America, it only peaked at No. 10 on Billboard’s Hot 100 chart. Written by band members Brandon Flowers and Dave Keuning, the song was born out of Flowers' paranoia one sleepless night that his girlfriend was cheating on him. Turns out, she was, and “Mr. Brightside” was born, mixed with crazy, catchy musical composition by Keuning. The lyrics center on a man who's sick over the prospect of imagining his lover with someone else. The song feels like a boxing match for your emotions, complete with pleading lyrics like, “It was only a kiss / it was only a kiss,” punk beats and a sarcastic sense of looking on the bright side — Flowers was right after all. It’s one of my favorite songs of all time to sing along with, whether I’m jamming in my car or dancing my face off to it after requesting it at a wedding. I truly believe that for the 2000s and beyond, it’s one of the best songs ever recorded. AHS

12. "Good Lord Lorrie" by Turnpike Troubadours (2012)
Album: Goodbye Normal Street
Songwriter: Evan Felker

“Lorrie lit a cigarette and smiled and waved the smoke out of her face
With her black hair brown from the summer sun
Green eyes looked around the place
And she told me that she loved me
And I grinned and grabbed her hand and said, ‘I know’
Let's get from here, now darling if we're going, let's go on and go”

It’s vital to begin this song review of “Good Lord Lorrie” with its opening lyrics to show how Evan Felker is a king of observational storytelling. It’s always the seemingly minor details for Felker, the frontman for the now massively popular red dirt band, Turnpike Troubadours. In this instance, waving the smoke out of her face, her green eyes, her black hair brown from the summer sun – he just sets this scene so perfectly. His lyrics are poetry. The song appeared on the band’s second album, Goodbye Normal Street, released in 2012. ‘Lorrie’ follows Lorrie, a recurring character in Turnpike songs, and her boyfriend as their doomed relationship from the start begins to unravel as he drunkenly makes a fool of himself. Beyond the lyrics, the melody itself is captivating with guitars, fiddle and drums. The opening drumbeats uniquely grab the listener's attention, almost announcing, “Get ready, you’re about to hear something amazing.” Felker’s southern drawl and pleading vocals on lines like, “Well, good lord Lorrie, I love you, could it go more wrong,” and practically yelling, “Guess your folks were right,” add to the song’s intensity. Felker has written many unique and beautiful songs since their first album 15 years ago, but “Good Lord Lorrie” will always be one of their best and one of the best in country music. AHS

11. "Living the Dream" by Sturgill Simpson (2014)
Album: Metamodern Sounds in Country Music
Songwriter: Sturgill Simpson

I credit Sturgill Simpson’s “Living the Dream” with helping me through a rough time in life. I was out of a job, didn’t know where I’d be headed in my life, and something about the sarcasm of the lyric, “I don’t have to do a goddamn thing, except sit around and wait to die,” proved to be a rallying cry for me. I didn’t take the line literally – I don’t think Simpson meant for it to be taken literally – I took it as a challenge to get out there and find something better in life. It obviously doesn’t help that a crying guitar line hits my soul like few other sounds, and I love Simpson’s Kentucky slurring drawl so much, and “Living the Dream” has it at its full peak. JS

10. "Grindin'" by Clipse feat. Pharrell Williams (2002)
Album: Lord Willin'
Songwriters: Gene Thornton, Terrence Thornton, Pharrell Williams & Chad Hugo

Songs can be iconic for various reasons, including their lyrics, cultural impact, and record sales. The single thing that makes “Grindin’” by Clipse feat. Pharrell Williams so iconic in the beat. “Grindin’” is one of the best beats in the history of music. You can hear the beat and instantly recognize the song without hearing a word. This was Clipse's debut single, and it instantly became a favorite among hip-hop fans —a rarity in itself. Featured on this song was Pharrell Williams of the iconic group the Neptunes, so it's no surprise that this beat was so iconic with his involvement. This song peaked at No. 30 on the Billboard Hot 100 in 2002. That's not bad, but it also shows that there is more to an iconic song than its position on the Billboard charts. This is not only one of the best songs in hip-hop over the last 25 years, but it is also one of the greatest overall tracks in the history of the genre. CB

9. "Hey Ya!" by Outkast (2003)
Album: Speakerboxxx/The Love Below
Songwriters: Andre Benjamin

Whether you’ve listened to it once or hundreds of times, “Hey Ya!” by hip-hop duo Outkast is always fun. From the catchy lyrics to the infectious dance beat, it’s a song that you just knew would last, even when it first came out in 2003. It was the second single off their fifth album, Speakerboxxx/The Love Below, and while the song is bouncy and cool, it’s not fluff. It’s a party song with a message. The lyrics, written by André 3000, discuss love and the dissatisfaction with the pressures society puts on relationships. He points this out with one of the best lyrics in the song: “If what they say is 'Nothing is forever' / Then what makes, then what makes / Then what makes, then what makes (what makes, what makes) / Love the exception?” It's ironic because it's a banger of a wedding song. The fun beat paired with the darker-toned lyrics makes it an extremely clever song. André 3000 even alludes to it by singing, “Are we so in denial when we know we’re not happy here? / Y’all don’t want to hear me, you just want to dance.” It’s societal commentary that's also asking listeners to “Shake it like a Polaroid picture.” The effort to record the song is fascinating for music production fans, as he heavily experimented with the sounds, recording each line dozens of times. In 2021, “Hey Ya!” was No. 10 in Rolling Stone’s list of the “500 Greatest Songs of All Time.” AHS

8. "Someone Like You" by Adele (2011)
Album: 21
Songwriters: Adele & Dan Wilson

British pop singer Adele is quite simply one of the best vocalists of all time. Her heartbreaking lyrics matched to her incredible vocals have brought many to tears for nearly two decades. Adele has universal appeal. Six-year-old girls love her as well as 85-year-old great-grandfathers. That makes it no surprise that her hit song, “Someone Like You,” would make it on the list of the best songs of the 2000s. The song went to No. 1 on the Billboard Hot 100 and won the inaugural Grammy Award for Best Pop Vocal Performance. The song is a relatable one about a woman who has been left by the love of her life, and she has recently learned that he is with another woman. She tells him that she will find someone like him and wishes him nothing but the best but still wants him to remember her and the time they shared with fond memories. Anyone who has experienced heartbreak will relate and fall in love with this song. It is difficult to find a song like this that is this good. TG

7. "Hurt" by Johnny Cash (2003)
Album: American IV: The Man Comes Around
Songwriters: Trent Reznor

Few legendary artists get to go out with such an emotional and iconic song as Johnny Cash did with his cover of the Nine Inch Nails song “Hurt,” which appeared on his 2002 album, American IV: The Man Comes Around, the final album released during his life. Many believe it to be the greatest cover song of all time, as Cash’s devastatingly heartbreaking vocals pull every bit of emotion out of Trent Reznor’s lyrics. The epic music video, directed by Mark Romanek, featured an aged and frail Cash, interwoven with images from his entire life and career, which helped certify it as timeless and one of the greatest music videos ever made. The music video won the Grammy Award for Best Video of the Year, and in 2011, NME magazine ranked it as the greatest ever made. It’s the perfect combination of lyrics, performance and film all wrapped into one to make one of the most haunting songs ever released. JS

6. "What Was I Made For?" by Billie Eilish (2023)
Album: Barbie the Album
Songwriters: Billie Eilish & Finneas O'Connell

I did not get the hype around Billie Eilish at all. In fact, I rolled my eyes when she managed to win all four of the General Field awards at the Grammys (Album, Song, Record, and Best New Artist of the Year). I did not get her. I never thought I would. Then, in 2023, Eilish released the song, “What Was I Made For?” from the “Barbie” soundtrack. I was haunted by complex emotions that I had kept within for far too long. It stirred something in me in a way that music hopes to do for its listeners. This song prompts us to reflect on our actions, our purpose and our emotions, and encourages us to contemplate what our lives are and what we aspire for them to be. This incredible song went on to win the Academy Award for Best Original Song. It shockingly only went to No. 14 on the Billboard Hot 100. It was met with universal acclaim from critics, and in my opinion, it is Eilish’s best song to date. TG

5. "Alabama Pines" by Jason Isbell & the 400 Unit (2011)
Album: Here We Rest
Songwriters: Jason Isbell

Jason Isbell has been one of the best singer-songwriters of the last quarter-century. His 2011 Americana Awards Song of the Year, “Alabama Pines,” from his and his band the 400 Unit’s Here We Rest album, was my introduction to his music, and remains my favorite song of his all these years later. Isbell has a way of writing emotional lyrics that feel completely lived in, and speak to listeners like me who can identify with soul-crushing lyrics like, “the AC hasn’t worked in 20 years/probably never made a single person cold/but I can’t say the same me/I’ve done it many times” and “No one gives a damn about/the things I give a damn about/liberties that we can’t do without/seem to disappear like ghosts in the air/when we don’t even care/it truly vanishes away.” Everything Isbell has done since the songs has been terrific, but nothing has spoken to me personally in quite the same way. JS

4. "Seven Nation Army" by The White Stripes (2003)
Album: Elephant
Songwriters: Jack White & Meg White

There has been no sound in pop music more ubiquitous in the last quarter-century than the amazing opening guitar riff of The White Stripes’ “Seven Nation Army,” released in 2003, played by Jack White. The riff and song are everywhere, including becoming a staple at sporting events around the world. Interestingly, the riff doesn’t even sound like a guitar – but rather a bass – which was created by Jack White playing his guitar through a pitch-shifting effect and lowering the pitch by an octave. It’s just Jack White playing guitar and Meg White playing a simple drumbeat, and somehow they created potentially the sound of the century. The winner of the Best Rock Song Grammy ranked No. 36 on a recent Rolling Stone magazine list of the 500 Greatest Songs of All Time. It’s the rare case, in my opinion, of a song that might appear on such a list even if it didn’t have any lyrics. Those lyrics, however, were actually written the night before the song’s recording, and see the band fighting against their rising stardom and the rumors surrounding the duo, who were actually married and divorced before their band hit it big. JS

3. "Long Walk Home" by Bruce Springsteen (2007)
Album: Magic
Songwriter: Bruce Springsteen

Bruce Springsteen has always had a dream for a greater America, while being painfully aware of times when it's been less than it could and should be. Some of the tunes can seem rather dour on the surface, but there’s always a bit of hopefulness within to give us hope heading into the future. None of his output of the last quarter-century has this mix of “things are tough, but we’ll make it through” theme better than “Long Walk Home,” from 2007’s Magic. “Long Walk Home” came about out of some of the toughest times of the President George W. Bush administration, when it looked like America might be losing its way with an unnecessary war and struggles through recession, but it has almost lived on to a greater degree in today’s America, where things have somehow gotten worse. “Long Walk Home” – like Springsteen’s “My Hometown” two decades prior – features the conversation of a father and a son, that’s always struck me as the heart of the song, in which the father says, “You know that flag flying over the courthouse/means certain things are set in stone/who we are, what we’ll do and what we won’t.” There’s no telling what our leaders will do anymore, but we don’t have to stand around and follow blindly. It’s going to be a long walk home, indeed. Springsteen has hope we’ll get back to where we belong. Because of songs like this, I do too. JS

2. "The House That Built Me" by Miranda Lambert (2009)
Album: Revolution
Songwriters: Tom Douglas & Allen Shamblin

“The House That Built Me” will always be country singer Miranda Lambert’s best song. Despite her impressive discography, she caught lightning in a bottle with this one. The song was supposed to be recorded by her ex, Blake Shelton, but Lambert was immediately drawn to it. Because of her vulnerability, it has become something uniquely intimate to her fans. It’s a song with such soulful nostalgia, this desire to visit where we came from when the world gets overwhelming. Written by Tom Douglas and Allen Shamblin, it was the second release off her third studio album, Revolution. It’s country music storytelling at its finest, centering on a person visiting their childhood home to recapture a sense of innocence and see if “this brokenness inside me might start healing.” Lambert’s Southern voice leans into the ache of yesteryear on chorus lines like, “If I could just come in, I swear I'll leave / Won't take nothin' but a memory / From the house that built me.” It became the song that built her career as her first No. 1 hit on the Billboard Hot Country Songs chart, where it stayed for four weeks. It’s a powerful one to see performed in concert because, as fans sing every word, she is genuinely tearful and grateful for it. AHS

1. "All Too Well" by Taylor Swift (2021)
Album: Red (Taylor's Version)
Songwriter: Taylor Swift

“All Too Well” was already ranked as Rolling Stone magazine’s No. 1 Taylor Swift song of all time before the extended 10-minute version was released in 2021. It was a song from Swift’s fourth studio album, Red, that, despite never being released as a single, grew a massive following. It became one of the Swifties’ favorite songs in her catalog. She had been interviewed years prior, where she mentioned that the song originally was 10 minutes long before she trimmed it down to the length of a typical album song. When Swift famously started re-recording her first six albums to gain ownership of her work, she decided to release the full 10-minute version of the song for her fans. I don’t think anyone was in for what we were given. The almost near-perfect song became simply perfect. With more gut-wrenching, poetic and heartbreaking lyrics, the 10-minute version gave us all a clearer picture of the story we were previously only given a glimpse of. When Red (Taylor’s Version) came out in 2021, “All Too Well” went No. 1 on the Billboard Hot 100, becoming the longest song to ever top the chart. The song went on to be nominated for Song of the Year at the Grammys and has cemented itself in history as one of THE best breakup songs of all time. It is a song we will always cry to, and even when the memories start to fade, we will still remember it, “All Too Well,” because it is the best song of the last quarter-century. TG

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