Tom Petty's 40 Greatest Songs

by Julian Spivey
Tom Petty and the Heartbreakers embarked on a nationwide tour in April that includes over 50 shows in 25 states with the occasional show in Canada and the United Kingdom to celebrate the group’s 40th anniversary. The Rock & Roll Hall of Famers will wrap up their tour in late September with three shows at the Hollywood Bowl in Los Angeles. The group has become one of the most popular classic rock bands in America with 13 studio albums, three Petty solo albums and almost 70 singles.

Tom Petty once told The Telegraph: “Music is probably the only real magic I have encountered in my life. There’s not some trick involved with it. It’s pure and it’s real. It moves, it heals, it communicates and does all these incredible things. It’s been so good to me that I want to be good to it. I want to make music that’s worth making.”
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For 40 years Petty has made music worth making and his music has been pure and real. It’s moved and it’s healed. It’s made people scream at the top of their lungs in concert and with the windows rolled down on the highway. It’s made the lives of all of us graced with its presence just a little bit better and that’s something that honestly just can’t be appreciated enough.

Here are the 40 greatest Tom Petty songs of all-time:

40. "Scare Easy"
Before the Heartbreakers was Mudcrutch. And, Mudcrutch could’ve been one of the greatest country-rock bands there ever was. Petty formed the band in the early ‘70s in his hometown of Gainesville, Fla. with Tom Leadon, brother of original Eagles member Bernie Leadon. The band also consisted of guitarist Mike Campbell and keyboardist Benmont Tench, both of whom would later join Petty’s Heartbreakers. Mudcrutch broke up in the mid-70s, but reformed in 2008 with a self-titled debut featuring the rootsy “Scare Easy,” kind of an “I Won’t Back Down” with a twangier vibe. 

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39. "It's Good to Be King"
“It’s Good to Be King,” from Petty’s solo 1994 album Wildflowers, is the 66-year old artist’s go to jam song in concert. It’s a laid-back vibe with Petty dreaming about how he’d run the world if he could be king. It sounds like a blast, but as Petty relents, “Can I help it if I still dream from time-to-time?” “It’s Good to Be King” features one of the best guitar solos in Petty’s discography, likely played by Heartbreakers guitarist Mike Campbell, and showing some beautiful maturity wraps up with an orchestra of strings conducted by Michael Kaman. 

38. "The Apartment Song"
Sometimes you just want something fun and mellow to jam along with and Petty hit that perfectly with “The Apartment Song,” off his first solo release Full Moon Fever in 1989. It sounds like a fun little two-and-a-half-minute pop song, but if you listen to the chorus: “Oh, yeah, I’m alright/I just feel a little lonely tonight/I’m okay, most of the time/I just feel a little lonely tonight” you realize it’s not all that fun, just catchy. Good pop-rock songs can almost trick you into enjoying loneliness with a bouncy groove. 

37. "Shadow of a Doubt (Complex Kid)"
I’ve never heard Tom Petty referred to as a punk rocker, but some of his output from the late ‘70s when he was first hitting the scene comes off that way to me. It’s in the sneering growl he has in his voice when he sings stuff like the chorus: “Yes, she likes to keep me guessing/She’s got me on defense/With that little bit of mystery/She’s a complex kid/And, she’s always been so hard to figure out/Yes, she always likes to leave me with a shadow of a doubt.” I don’t believe this song off 1979’s Damn the Torpedoes would’ve sounded foreign on an Elvis Costello album of the same era. 

36. "Melinda"
Tom Petty could’ve been a legend at any specific genre whether rock, pop, country or blues – he’s proven that with a wide variety of songs throughout his illustrious career. “Melinda,” which appears on his The Live Anthology release from 2009, shows Petty’s blues prowess. The song recorded live in August of 2003 in New Orleans about going down to see this mysterious Melinda is one of the great deep cuts never released on any Petty studio album. It turns into an eight-plus minute jam session on the live record featuring terrific piano playing from co-writer (with Petty) Benmont Tench. 

35. "Friend of the Devil"
I realize that it’s unusual and probably not the “cool” thing to do to include a cover on such a list, but dammit Tom Petty & the Heartbreakers’ live cover of the Grateful Dead classic “Friend of the Devil” from The Fillmore in San Francisco (Grateful Dead territory) in 1997, which appears on The Live Anthology, is one of the all-around best covers I’ve ever heard. It’s a typical Dead story/travel song written by Jerry Garcia, Robert Hunter and John Dawson and the Heartbreakers get the jam-band, hippie feel down pat. I believe Deadheads everywhere would be pleased. 

34. "A Thing About You"
Already on this list I’ve compared Tom Petty’s brand of rock to punk music and country music and said he could’ve done any genre he set his mind to do, and honestly, he has. “A Thing About You,” from the Heartbreakers’ fourth studio album Hard Promises in 1981 is terrific proof of this. Petty’s version is hard-charging, especially in the chorus that can come off punkish with his Southern drawl. Country band Southern Pacific with a little help from the legendary Emmylou Harris took a slowed down, countrified version to the top 20 on the country charts in 1985. 

33. "Trailer"
Sticking with the Petty as a country singer theme there’s my favorite Mudcrutch song “Trailer” from 2016 (the most recent song to appear on this list). I was happy to see Petty’s original group Mudcrutch return last year with Mudcrutch 2, eight years after the band’s debut. “Trailer” is a nostalgic country-rocker about falling in love with a girl and giving everything to her, even the titular home, where they spend their years together. Petty evidently had been holding on to this one for a while, as “Trailer” was intended for his 1985 Southern-themed album Southern Accents before failing to make the album. 

32. "A Woman in Love (It’s Not Me)"
Tom Petty did moodiness very well in the late ‘70s/early ‘80s, which really set his rock music apart from some of the other popular acts of the time. The almost noir-ish moodiness of “A Woman in Love (It’s Not Me),” off 1981’s Hard Promises, really comes off in the spoken twangy drawl of the verses about a woman who used to love our narrator and is in love once again – but with someone new. It’s a very cinematic track and one pianist Benmont Tench calls “brilliant.” He told Songfacts: “I like the way the track breathes. There is a lot of space, there are a lot of places where there’s only drums, bass and one guitar playing with a vocal. I like the air in that song. I like the way that the beat picks up a little and then drops down in tempo and picks up for the chorus and then drops back down for the verses. I really like that. I thought it was a brilliant song.”

31. "Listen to Her Heart"
One of Tom Petty’s obvious heroes is the legendary Bob Dylan and the two would become friends as members of the ‘80s supergroup Traveling Wilburys (along with George Harrison, Roy Orbison and Jeff Lynne). One thing Petty seems to do as well as Dylan is the kiss-off song. “Listen to Her Heart,” a short, catchy rocker from 1978’s You’re Gonna Get It!, is a song about a man trying to steal the narrator’s woman and how he’s irritated by this, but knows she’ll remain with him. Petty reportedly said during a radio interview that “Listen to Her Heart” was in response to musician/songwriter Ike Turner making advances upon his then wife Jane Benyo. 

30. "I Should Have Known It"
Tom Petty and Mike Campbell always loved the sound of bluesy-rock and finally set out to make a blues-rock record in 2010 with Mojo. Petty told Rolling Stone the album wasn’t music for radio or big arenas, but “for the band to play.” Though, having seen the band perform “I Should Have Known It,” the best of Mojo, twice in concert it goes over swimmingly in big arenas. It’s a sound of the Yardbirds era, another influence on the Heartbreakers, and shows the band can still get loud and raw into their fifth decade of performing together. 

29. "The Waiting"
“The Waiting,” off Tom Petty and the Heartbreakers’ 1981 album Hard Promises, was one of the group’s biggest hits topping the newly-founded Billboard Rock Tracks chart for six weeks and making the top 20 overall on the Billboard Top 100. It’s easy to see how it became one of the group’s biggest hits being a catchy, sing-along type with its chorus. Petty said to Rolling Stone: “It was about waiting for your dreams and not knowing if they will come true. I always felt it was an optimistic song.” He may have also borrowed the title from the famous Janis Joplin quote: “I love being onstage, everything else is just waiting.” 

28. "You Got Lucky"
“You Got Lucky” was the first single from Tom Petty and the Heartbreakers’ 1982 release Long After Dark and became a hit in the MTV era with a “real groundbreaker” of a video, according to Petty, that was influenced by the hit 1981 film “Mad Max 2: The Road Warrior.” Like “The Waiting” the year before, “You Got Lucky,” a perfectly and arrogantly machismo romp about how a woman got lucky when she found the narrator and giving him up would be her mistake, topped the Billboard Rock Tracks chart and went top 20 overall on the singles chart. The song would feature a synthesizer, which Petty would tell an interviewer that Benmont Tench was angry about having to play. The synth would come in handy a few years later … 

27. "Don’t Come Around Here No More"
Tom Petty set out to sort of record a concept album about living in the South with 1985’s Southern Accents, but when he also set out to record “a single that sounded like nothing anybody had ever done” he ended up with “Don’t Come Around Here No More” (reportedly taken from a breakup line Stevie Nicks used on Joe Walsh) and the concept kind of went out the window. Petty and the band did accomplish something that sounded completely new with the synth-y, sitar-aided (played by producer and Eurythmics member Dave Stewart) track that became a huge hit with its Alice in Wonderland inspired music video that would become one of the most famous in MTV history. 

26. "You Wreck Me"
Tom Petty went solo for his mid-‘90s hit Wildflowers, but the terrific track “You Wreck Me” sounds completely Heartbreakers-ish and rightfully so as it was co-written with Mike Campbell and featured every member of the Heartbreakers, except for drummer Stan Lynch. The drummer on the track was Steve Ferrone, who would soon replace Lynch in the Heartbreakers. The song as Petty has stated sounded like it could’ve come straight out of 1980 for the Heartbreakers, though as Rolling Stone pointed out its “ragged riffs fit with the alt-rock ‘90s too.” 

25. "Anything That’s Rock & Roll"
You’ve got to go all the way back to the debut of Tom Petty and the Heartbreakers and their self-titled album, released at the end of 1976, for “Anything That’s Rock & Roll” (the group’s second single after “Breakdown”). Petty and the Heartbreakers were as American rock as you could be coming from Florida with a Southern twang, but surprisingly made a name for themselves initially on the charts in the United Kingdom with this track (one that was never released in the U.S.) – a quick romp about any kind of rock ‘n’ roll music being just fine by them. We know that the group was inspired by acts like The Byrds, but this track was sort of New Wave-ish and sounded like it could’ve been right at home in the discography of another great American rock band debuting around that time The Cars. 

24. "I Need to Know"
Kind of keeping with that New Wave rock sound of the late ‘70s comes 1978’s “I Need to Know,” the lead single off the group’s second album You’re Gonna Get It!. It’s another simple, short rocker (actually the same length as “Anything That’s Rock & Roll”) about the narrator needing to know whether his lover is going to skip town on him. Petty’s vocal intensity on the record with the narrator’s impatience really gives the song a needy drive to it. The group fresh off their first American top 40 single, the re-release of “Breakdown” from their debut album, wanted to get something out hot and succeeded with this one. 

23. "Yer So Bad"
“Yer So Bad,” off Petty’s solo effort Full Moon Fever in 1989, is one of the artist’s more fun tunes, even though (especially because?) of its black humor that sees the narrator talking of things such as his “sister’s ex-husband who can’t get no lovin’” and the incredibly catchy chorus. It’s incredibly simple – just two verses and a chorus – but didn’t catch on with fans as well as “Free Fallin’,” “I Won’t Back Down” and “Runnin’ Down a Dream” when released as a single. Still, it’s one of the more fun tunes in Petty’s repertoire to sing and he frequently breaks it out in concert to this day. 

​22. "Square One"
In 2006 Tom Petty released Highway Companion, which saw him reunite with producer and Traveling Wilburys compadre Jeff Lynne who had produced his most successful solo release Full Moon Fever nearly 20 years prior. The album featured the contented “Square One,” which had debuted on the soundtrack of Cameron Crowe’s film “Elizabethtown” the year before and earned Petty a Grammy nomination for Best Song Written for a Motion Picture. The softly performed track sees Petty in a happier mood than we had seen in the years prior after his marriage ended and he battled drug addiction, “I’ve gotten through the dark tunnel and come out the other side” he remarked at the time of its release. 

21. "Down South"
Also appearing on Highway Companion was “Down South,” which I like to think is somewhat of a sequel to his brilliant “Southern Accents” from 20 years before in that it expertly captures the essence of Southern life. The album had a great listen-while-driving vibe to it with its heartland rock and sing-along qualities and “Down South” includes terrific lines like “impress all the women/pretend I’m Samuel Clemens/wear seersucker and white linens” along with an extremely catchy chorus. In 2005, Rolling Stone named it the third best song written about the South. 

20. "Saving Grace"
I didn’t intentionally place three songs from Highway Companion consecutively on this list, but that just goes to show how great of a sound Tom Petty had on that album. “Saving Grace” is a terrific driving song. It just feels like the kind of track you want to put on while going over the speed limit with the windows down and wind whipping through your hair. “Saving Grace” has a nice rockabilly feel to it, while also throwing in some John Lee Hooker “Boom Boom”-esque riffs. Next time you’re driving put this one on and let it be your highway companion. Just keep an eye on that speedometer. 

19. "Here Comes My Girl"
I totally wanted the chorus of Tom Petty and the Heartbreakers’ “Here Comes My Girl,” from their stupendous 1979 Damn the Torpedoes album, to play at my wedding when my wife walked down the aisle. It was a Catholic wedding though, so that didn’t happen. It’s such a badass song about how awesome the narrator’s girl is – simple, but perfect in its simplicity. Petty has said the chorus was inspired by one of his favorites, The Byrds, but guitarist Mike Campbell said Petty had trouble with the verses – singing them at first before eventually going with a Shangri-Las influenced spoken word. 

​18. "Crawling Back to You"
Tom Petty has said a few times in interviews that he’d love to tour the Wildflowers album after he and the Heartbreakers are done with their 40th anniversary tour. It’s such a damn good album I hope he gets his wish. “Crawling Back to You” feels like one of the most open songs on the album. Petty’s marriage was falling apart around this time and it really comes through in the vocal. Before recording Wildflowers, Petty’s cousin had sent him a book of great phrases. One such phrase Petty really liked, “Most things I worry about never happen anyway,” which he worked into this song. In a 2016 readers’ poll conducted by Rolling Stone this was named the greatest Tom Petty deep cut by fans. 

17. "Don’t Do Me Like That"
Believe it or not, “Don’t Do Me Like That” is the highest charting hit for Tom Petty and the Heartbreakers (his solo “Free Fallin’” would chart higher in 1989). That’s probably because its brisk pace and rapid vocals by Petty make it perfect for radio consumption. “Don’t Do Me Like That,” the first single off Damn the Torpedoes, topped out at No. 10 in 1979. As these things often go, Petty thought it was kind of a lightweight track and producer Jimmy Iovine even initially dismissed it. The title came from something Petty’s father used to say. “I thought it was humorous,” Petty would later say. 

16. "Learning to Fly"
“Learning to Fly” was written by Tom Petty and producer/collaborator Jeff Lynne after Petty was inspired by a televised interview with a pilot who said, “There’s not much to learning to fly; the difficult thing is coming down.” It’s a pretty good metaphor for life. The song, which would become a No. 1 hit on the Billboard Rock Tracks chart, is one of Petty’s more reassuring and inspirational song. “I wanted that song to be a kind of redemptive song,” he told Rolling Stone. Guitarist Mike Campbell lauded the simplicity of it: “That’s the miracle of the song. There’s really not much to it. It’s really simple music, simple lyrics.”

15. "Into the Great Wide Open"
Tom Petty really isn’t known for story songs. He just doesn’t write many songs that would be considered as such, but “Into the Great Wide Open,” from the 1991 album of the same name, ranks as one of the best in rock history. “Into the Great Wide Open” is the tale of Eddie, a guitar slinging “rebel without a clue” who goes to Los Angeles and experiences a rather quick rags-to-riches-to-rags story in the music industry. The song is one of Petty’s most notable music videos and features two Hollywood superstars Johnny Depp, playing Eddie, and Faye Dunaway. Petty portrays four different characters in the video, including Eddie’s roadie named Bart. “Into the Great Wide Open” is likely the story of many one-hit wonders who’ve gone through the music industry ringer. 

14. "Wildflowers"
Tom Petty isn’t really known for sweet songs – ones that will tug at your heartstrings, but “Wildflowers,” the title track from his solo 1994 album, will hit you in the feels. “Wildflowers,” a gentle folk-influenced tune has Petty singing to someone close in his life – potentially a child (the song has become a popular father of the bride dance number at wedding receptions). Like with many folk songs, it’s beautiful in the simplicity of its lyrics like, “you belong among the wildflowers/you belong in a boat out at sea/run away, kill off the hours/you belong somewhere you feel free.” 

13. "Louisiana Rain"
“Louisiana Rain,” the final track off Tom Petty and the Heartbreakers’ breakthrough 1979 album Damn the Torpedoes, is definitely one of my favorite Petty deep cuts. A Rolling Stone readers’ poll conducted in 2016 had it ranked as his fourth greatest deep cut behind “Luna,” “Straight Into Darkness” and “Crawling Back to You” (No. 18 on this list). It’s so deep a cut Petty has played it fewer than 10 times in his touring career, though a live version from London’s Wembley Stadium in 1982 did make The Live Anthology release. Producer Jimmy Iovine scoured through every bit of Petty’s vault when recording the album to make the cut. He came across this Mudcrutch-era song and loved it. The emotional ballad is a great way to finish out a breakthrough release of triumphant songs. 

12. "Even the Losers"
“Even the Losers” is one of those triumphant songs off Damn the Torpedoes. “Even the losers get lucky sometimes” is one of the most stellar lyrics ever when it comes to someone who isn’t maybe the most popular person in his class or world still being able to fall in love. Like in the song, though, unfortunately it doesn’t always last. The first verse, in particular, is so perfectly cinematic it showed Petty was going to be a songwriter for the ages: “It was nearly summer, we sat on your roof/Yeah, we smoked cigarettes and we stared at the moon/I showed you stars you never could see/It couldn’t been that easy to forget about me.” 

11. "Walls"
“Walls” is one of the most beautiful songs Tom Petty has ever written. And as Petty once said, “It probably should have been a hit.” The song was written for the Edward Burns movie “She’s the One,” for which Petty did the soundtrack. Part of the reason why it probably wasn’t a hit or released as a single is there are multiple version of the song that appear in the film: “Walls (Circus)” and “Walls (No. 3). My favorite version is “Walls (No. 3),” which has a more beautiful melody and vocal and is the version played by Petty live to this day. The song was based on something Johnny Cash said to Petty that ended up as a lyric: “some days are diamonds and some days are rocks.” 

10. "The Last DJ"
I love artists when they have something important to say or get off their chest. Tom Petty’s 2002 release “The Last DJ,” from the studio album of the same name, really seems to have that going for it. On its surface “The Last DJ” seems like an anti-radio establishment song about a DJ who doesn’t want to go corporate and wants “to play what he wants to play and say what he wants to say.” This got the song banned from stations owned by Clear Channel Communications (which seemed to really like to ban songs – Petty’s “Free Fallin’” was among many songs banned briefly following 9/11). Petty told Mojo magazine in 2010 that the song was often misunderstood as “Radio was just a metaphor. [The song] was really about losing our moral compass.” 

9. "Refugee"
“Refugee,” from 1979’s Damn the Torpedoes, is one of Tom Petty and the Heartbreakers hardest rocking songs and still one of their most popular today among fans – believe me I saw the reaction firsthand at Little Rock’s Verizon Arena in April. Around the time of the songs release traditional rock music was struggling – it was under siege from subgenres like punk rock or new wave (both of which Petty and the Heartbreakers had been considered and often with good reason), but Petty wanted to show people that the group was an old-fashioned rock band and did so with this track that reached No. 15 on the Billboard singles chart. Doing so took a lot of recordings though – guitarist Mike Campbell says 100 takes were recorded; Petty says it could have been as high as 200. In 2014, Rolling Stone ranked it as Petty’s second greatest song of all-time, behind “American Girl.”  

8. "You Don’t Know How It Feels"
“You Don’t Know How It Feels,” from Tom Petty’s 1994 solo album Wildflowers, was his last top 40 hit – reaching No. 13 on the Billboard singles chart. It also made it all the way to the top spot on Billboard’s Rock Tracks chart. “You Don’t Know How It Feels” is a laid back rootsy song with a terrific harmonica solo that has one of my favorite snarky Petty lyrics of all-time: “My old man was born to rock/He’s still tryin’ to beat the clock/Think of me what you will/I’ve got a little space to fill” before breaking into a small guitar solo. It’s the greatest way to finish a verse when you don’t have a rhyme. 

7. "Southern Accents"
“Southern Accents,” from the 1985 album of the same name, is without a doubt my favorite Tom Petty and the Heartbreakers deep cut and it has always felt like one of the more personal and maybe biographical songs in his discography. It’s one he doesn’t play very often in concert. The song is about being proud of who you are and where you come from. “I came from a real Southern family, and I wanted to address that world,” Petty, a native of Gainesville, Fla., said. Fellow Southern musician Johnny Cash liked the song so much he recorded it for his 1996 Unchained album, which featured Petty and the Heartbreakers as his studio band. Cash told Petty the song was so good he could see it replacing “Dixie” as the region’s unofficial anthem. I believe it’s the greatest song ever written about the South. 

6. "Runnin’ Down a Dream"
Even though 1989’s Full Moon Fever was billed as a Tom Petty solo release every member of the Heartbreakers would play on it except for drummer Stan Lynch and it’s Mike Campbell’s heavy opening guitar riff that really makes “Runnin’ Down a Dream,” the album’s second single and a top 25 Billboard hit, stand out. It’s likely one of the most memorable rock guitar riffs of all-time. “Runnin’ Down a Dream,” like much of Petty’s heartland rock-sounding tracks, makes for a perfect driving song as it makes you want to roll down the windows and break the speed limit like the narrator in the song. The song includes a lyrical tribute to Del Shannon’s “Runaway,” a No. 1 hit in 1961, that Petty loved as a kid. 

5. "Breakdown"
“Breakdown” was the very first single Tom Petty and the Heartbreakers ever released when they made their debut in 1977 with their self-titled album. It didn’t go anywhere. But, one year later when the band re-released the song, after “Anything That’s Rock ‘n’ Roll” and “American Girl” had success in the U.K., it became the group’s first Billboard Top 40 hit. One of the group’s greatest jams the single features one of Mike Campbell’s best guitar licks and one of Petty’s most passionate and even somewhat menacing vocals. The version you’ll hear on the radio is barely over two-and-half-minutes, but when performed in concert the group turns it into the seven-to-10-minute jam session it was originally meant to be – which can be heard on The Live Anthology. The song was inspired by R&B songs of the early ‘60s and Petty will often incorporate Ray Charles’ “Hit the Road Jack” into performances. 

​4. "I Won’t Back Down"
“I Won’t Back Down,” a No. 12 charting single off 1989’s Full Moon Fever, is Tom Petty at his most defiant and straight-forward. This bugged him when he finished the song. “That song frightened me,” he told Rolling Stone. “There’s not a hint of metaphor in this thing. It’s just blatantly straight-forward. I had a lot of second thoughts about recording that song. But everyone around me liked [it], and it turns out everyone was right.” Because there really isn’t a culprit of what’s trying to get the narrator to back down the song really works for anyone trying to stand tough in a bad situation. Maybe straight-forward, but that bit of vagueness was brilliant, as it leads to it meaning different things to different people. One of the most emotional performances of the song came after 9/11 when Petty performed a quieter version of it on television’s “America: A Tribute to Heroes” just two weeks after the tragedy. 

3. "Mary Jane’s Last Dance"
Tom Petty and the Heartbreakers’ greatest rockers are owed just as much to Mike Campbell’s fantastic guitar licks as they are to Petty’s songwriting and vocal performances. “Mary Jane’s Last Dance,” a single tacked onto 1993’s Greatest Hits compilation, is a great representation of this. It wasn’t even a new song and we almost never got to hear it. Petty’s record company wanted him to record new songs for the compilation, against his will, a practice often done to entice fans who may already have all an artist’s recordings, to spend their money. Petty had producer Rick Rubin go through old demos from his Full Moon Fever sessions and this one was the winner. According to Rolling Stone, the song’s “haunting chorus and bluesy guitar” were added and Petty had his first top 20 hit of the ‘90s. 

2. "Free Fallin’"
Even if you’re not a fan of Tom Petty and the Heartbreakers or hell even if you’ve never heard of Tom Petty and the Heartbreakers (you have serious problems, but still) you’ve heard “Free Fallin’.” “There’s not a day that goes by that someone doesn’t hum ‘Free Fallin’’ to me, or I don’t hear it somewhere,” Petty told Rolling Stone. The song off his 1989 solo release Full Moon Fever is the highest charting release of his career peaking at No. 7 on the Billboard singles chart (if you don’t include “Stop Draggin’ My Heart Around,” his duet with Stevie Nicks). The song pulls from what Petty witnessed on his frequent drives through Ventura Boulevard in the San Fernando Valley of California, but it was meant as a joke between him and producer Jeff Lynne until Lynne, liking the riff and verses, said randomly the words “free falling,” according to a Billboard interview with Petty. The rest is history. 

1. "American Girl"
It’s incredible to think that a band’s greatest song could come off its very first album, but that just goes to show what kind of songwriter Tom Petty has always been and what kind of a kickass band the Heartbreakers have always been. Now a classic radio staple and considered to be one of Petty’s greatest hits the song got little airplay when released in 1977, but after appearing on an episode of the BBC’s music series “The Old Grey Whistle Test,” the song charted in the United Kingdom. Petty and the Heartbreakers took a fast-charged jangling guitar riff and rapid vocals and made a song that sounded almost like a punk rock track while mixing ‘60s rock of The Byrds with a New Wave energy, according to Rolling Stone. It’s a song about trying to escape the monotony of daily life in a small town and trying to find something greater in the world. “The American Girl is just one example of this character I write a lot about – the small-town kid who knows there’s something more out there, but gets fucked up trying to find it I always felt sympathetic to her,” Petty told Rolling Stone. The song, which was fittingly recorded on July 4, 1976, is one you just can’t help but bob your head to and sing at the top of your lungs every time you hear it. It’s not Tom Petty and the Heartbreakers’ only masterpiece, but it’s their best one.