100 Best Americana & Country Songs of 2020 (Part 2: 75-51)

by Julian Spivey

75. "All in One Place" by Chicago Farmer
According to an article in American Songwriter, singer-songwriter Cody Diehkoff, who goes by the recording/stage name Chicago Farmer, thought he may have a small fortune headed his way in royalties when his song “Everybody In This Town” hit 10,000 plays on TouchTunes Jukeboxes. He received a check form TouchTunes for $11. That’s where the humor in the outlaw country-esque “All in One Place” come about. How you think you’re going to make something as a recording and traveling musician, but then the royalties or T-shirt sales or album sales can barely buy you dinner. Good thing most musicians aren’t in it for the money. 

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74. "Whiskey Kinda Night" by William Michael Morgan
Drinking songs have always and will always be part of country music and one of the best of 2020 was William Michael Morgan’s “Whiskey Kinda Night.” With a smooth vocal reminiscent of someone like Joe Nichols, Morgan tells of a love who’s left and how the only remedy for his pain is whiskey. Hey, it’s pretty simple and the type of theme that’s been done time and time again, but the vocal and laid back contemplative sound make the track, written by Morgan with Doug Johnson and Adam Wood, soothing to the ears. 

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73. "Crows and Buzzards" by Andy Brasher
One of the strangest recurring themes in particularly the genres of country and folk music has been the murder ballad, specifically the murder ballad of a man killing a cheating spouse or partner, which is admittedly jarring and I can understand why some people find it problematic, but dammit if there aren’t a lot of really well-written murder ballads and Andy Brasher’s “Crows and Buzzards” is one of them. The most unique aspect of “Crows and Buzzards” is just how mellow it sounds given its dark theme, which gives it that originality and different sound you’re always looking for from an often-used theme. 

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72. "Loving Her" by Katie Pruitt
“Loving Her” is a terrific love song by Katie Pruitt about her girlfriend and how she doesn’t care if anybody has a problem with the fact that she’s in love with a woman. She told The Boot: “I feel like this is one of those songs I’ve been trying to write my whole life. I’ve been trying to say a certain thing in a certain way, without coming across as upset or angry, because it’s really hard to talk about that and not be, you know, angry about it.” This song came from a hard conversation Pruitt had with her father about being in love with a woman and how he just didn’t understand it and how that made her feel. 

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71. "Can't Do Much" by Waxahatchee
Katie Crutchfield, who records solo as Waxahatchee, has recorded what she calls, “an extremely unsentimental love song, a love song with a strong dose of reality.” Her vocal is terrific and the song has a really lovely, relaxing melody to it that undoubtedly came from influences like Linda Ronstadt and Emmylou Harris. Crutchfield told Rolling Stone: “[The song] was written early on in a relationship, where the feelings were super intense, but also fear or apprehension were sort of keeping m from totally relaxing in it yet. Sort of like, ‘it’s annoying that I love you so much.’ Totally unromantic, which sort of makes it really romantic to me.” 

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70. "The First Thing I Reach For" by Ashley McBryde
“The First Thing I Reach For,” off Ashley McBryde’s Grammy-nominated album Never Will, is country as hell. McBryde and co-writers Mick Holland and Randall Clay pretty much wrap all your usual country music vices into one great song about knowing all these things are bad for you, but also knowing their easy – hence “the first thing I reach for is the last thing I need.” It’s a terrifically twangy number by one of the best mainstream country music has had to offer of late. 

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69. "Black Like Me" by Mickey Guyton
Once again, this year we saw that there are real disparities in the way some people live compared to others and how we can’t start to even things out until we realize the situation some folks are in. Mickey Guyton shouldn’t be an outsider, but simply being African-American (and a woman) in the country music genre has essentially made her one. Her song “Black Like Me” does a lot to help some folks who may be oblivious to the disparities faced in this country by folks who don’t look like them realize those disparities. Guyton sings about how “it shouldn’t be twice as hard” just to live in this country as a black person and how the fact that black folks shouldn’t have to do so in “the land of the free.” 

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68. "The Overthrow" by Will Hoge
I have to admit that if Joe Biden had not won the 2020 Presidential Election over President Donald Trump that this song would not have made this list. That seems like a weird reason to either add or leave a song off a year-end best of list, but the song is basically about the American people overthrowing President Trump, so had that not have happened it just would’ve been an awkward placement on the list and, frankly, I probably could not have bared listening to Will Hoge’s “The Overthrow” again. “The Overthrow” sees Hoge at his most punk (something I’ve likened him to in the past) as he basically is looking forward to the American people saying “enough is enough” to the “Darth Vader with a spray tan” in charge of the country. It would’ve been perfect for Hoge’s politically-charged 2018 release My American Dream, but as it stands makes for a great victory anthem. 

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67. "Knowing You" by Kenny Chesney
Kenny Chesney always seems to be at his best when singing nostalgic songs about lost loves or past love. His latest track featuring this theme is “Knowing You,” the highlight of his 2020 release Here and Now. The song, written by Adam James, Brett James and Kat Higgins, finds Chesney in that sweet spot vocally where he’s no longer with this woman, but just having spent time with her and known her will leave lasting memories for the rest of his life. 

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66. "Starts with You" by American Aquarium 
American Aquarium’s “Starts With You” is a fun listen with some awfully good lines like the opening “they say you’re only as sick as your secrets/if that’s the truth then, friend, I’m dying” and a verse about sad songs making the narrator (presumably AA front B.J. Barham himself) happy, but how he’s found a woman that’s made him smile than “every sad song ever written.” It’s the kind of love song I believe even the gruffest or most jaded among us could dig. 

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65. "On Borrowed Time" by Bryan James
If any year could make you believe every single word of Bryan James’s “On Borrowed Time” it’s certainly 2020. The song from his album Politics or Religion talks about the after-life and how nobody really knows what’s to come and how our time on Earth is just us being on borrowed time and how we should learn to live life like we only have a finite amount of it. It’s certainly a great lesson for us this year. 

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64. "Old Man" by Zach Bryan 
Zach Bryan sort of popped up out of nowhere in 2019 with videos of his stripped down country music just his vocal and a guitar going viral, which lead to a debut album DeAnn, which sounded much of the same. Bryan must have had the songs stacked up (or either he’s a real quick songwriter) as he was already onto releasing his sophomore album Elisabeth (definitely seems to be a theme developing with his album titles), which was just as stripped down as the first (which wasn’t necessarily by design, rather circumstances as Bryan is an active member of the U.S. Navy without as much free time as your average musician). The highlight of Elisabeth is “Old Man,” which honors fathers who sacrifice a lot by working hard and long hours to provide everything for their families. I would imagine Bryan’s inspiration was his own father, but it’s a beautiful tribute that anyone with a blue collar, hard-working dad can appreciate. 

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63. "The Cure" by Watkins Family Hour
The Watkins family is mighty damn talented when it comes to bluegrass and American roots type music as siblings Sara and Sean Watkins (both originally in the Grammy-winning bluegrass trio with Chris Thile) are incredibly talented and proficient at multiple string instruments. Watkins Family Hour, their group when not working on other projects, released the aptly titled Brother Sister this year that features the lovely “The Cure.” The first time I heard “The Cure” I felt it had religious meaning to it with the line “I avoided the cure, but it found me anyway,” as in I avoided God and religion, but it eventually found me instead of the other way. That was a misreading. I was hooked on the song either way. According to the group’s website “The Cure” was inspired by Sean watching “Tidying Up With Marie Kondo” on Netflix, while being in a bad relationship and hitting on the concept of throwing away those things you don’t need and love. 

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62. "exile" by Taylor Swift & Bon Iver
The most shocking thing on this year’s list for me is the inclusion of a Taylor Swift song. It wasn’t all that long ago when I thought Swift was one of the biggest problems with country music and bringing pop influences into the genre. Then she completely left country music behind to go pop (which I always felt she was anyway). And then this year she came out with folklore, an indie-folk release that showcases her songwriting in a more singer-songwriter fashion than any of her previous releases. There are multiple tracks on the album that could’ve made this list, but I’ve settled on “exile,” a duet with Bon Iver (another artist I’ve never cared much for as I thought he always sounded pretentious) as my choice. “exile” isn’t new territory for Swift, it’s a breakup song, but unlike much of her past breakup songs it sees things from both sides and really shows a maturation in the now 31 year-old’s work. 

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61. "Put On Your Brave Face Mary" by Reckless Kelly
One of the sad hypocritical realities of this country is how we send brave men and women off to war to fight for their country, calling them heroes and patriots all along, and then completely forget about them when they come home, often with wounds that can’t be seen. Reckless Kelly’s “Put On Your Brave Face Mary,” is a passionate telling of this problem and how the V.A. is understaffed and ill-equipped to deal with “demons they don’t understand” and how the politicians in Washington are just full of hot air and don’t seem to truly care about the tragic number of veterans who commit suicide on a daily basis. Willy Braun is at his most Bruce Springsteen-esque on this track that speaks to one of our nation’s least talk about and important issues. 

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60. "Outlaw Blood" by Ray Wylie Hubbard feat. Ashley McBryde
Ray Wylie Hubbard writes songs with so much specificity in them that I just can’t help, as a writer, but love. He also writes lyrics that seemingly only he could write or get away with like “her mama got a tattoo says, ‘free Sonny Barger’ or “She got mascaraed eyes and raven black hair, buys her shoes at Kim’s Exotic Dancewear.” I can’t say that I’d actually be interested in the type of women with the “outlaw blood” that Hubbard writes about in “Outlaw Blood,” but he sure makes them seem fun. I love that Hubbard not only features Ashley McBryde on harmony vocals, but also tributes her in a verse with the line, “loves to hear Ashley McBryde sing.” It’s cool that McBryde has already drawn that kind of love from one of outlaw country’s greatest. 

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59. "Her" by Randy Rogers & Wade Bowen
In 2015, Texas Country stars Randy Rogers and Wade Bowen teamed up for the terrific collaborative album Hold My Beer, Vol. 1, which featured one of my favorite songs of that year “Standards.” I was thrilled the two got together again to release Hold My Beer, Vol. 2 early this year and the album might even be better overall than their first effort. My favorite track off Vol. 2 is “Her,” which feels like an instant classic drinking song and story song wrapped into one like the kind of humorous thing Bobby Bare might have recorded in his heyday. It makes perfect sense that the song is a co-write between Buddy Cannon and Dean Dillon. The narrator of “Her,” sees a couple at the bar and has an eye for the woman, so he pulls up beside them on the next barstool, chats up the man and keeps supplying him with drinks until the guy is good and drunk, passes out and our narrator runs off with “her.”   

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58. "Marie" by Lori McKenna
Lori McKenna writes a country story song as good, if not better, than anybody else currently within the Americana or country music genres. Her latest album The Balladeer is “in some ways her life story,” according to her website. One of the most heartbreaking, but also resilient, songs on the album is “Marie,” about her older sister’s influence on her after the death of their mother at an early age. It’s a reminder of just how important one’s family can be during the hard times.  

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57. "Sometimes" by H.E.R.
For the second year in a row while watching the Grammy Awards, I was floored by a performance by H.E.R. In 2019 it was her performance of “Hard Place.” This year it was the performance of “Sometimes” and it has stuck with me all year. Let’s get one thing straight – H.E.R. is a R&B artist. So if you want to scoff at me passing her off as Americana for the purpose of this list go for it – but honestly isn’t Americana supposed to be this huge melting pot of musical forms that developed in this country and R&B and soul belong as much as country, folk, blues and what have you within the community. The vocals and guitar playing by H.E.R. on this track, which is an inspirational anthem about getting through life even when things aren’t going your way. 

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56. "Small Town Hypocrite" by Caylee Hammack
You wouldn’t know Caylee Hammack was merely 26 years old upon hearing “Small Town Hypocrite,” with such a maturity and knowing to it when it comes to someone dreaming of getting out of their small-town feeling their too good for it only to find themselves trapped there for seemingly eternity. The fact that such a song comes on her debut album, If It Wasn’t For You, is also remarkable. “Small Town Hypocrite” sees its narrator give up on her dreams at a young age to marry a high school sweetheart, only to settle down and have kids and have the guy leave. There’s much reality to Hammack’s song who gave up a music scholarship to Belmont University for a boy who told her he couldn’t go on without her. She may have given up on that particular dream, but something tells me Hammack is going to be OK. 

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55. "Someone to Use" by Hellbound Glory
Hellbound Glory is certainly no stranger to debauchery, but his most recent album proudly called Pure Scum makes debauchery sound smoother and classic countrier than he ever has on record before. One of the biggest highlights of the record is “Someone to Use,” a loving tribute to sex with no strings attached as a means of soothing away his loneliness. Sure, it’s not going to make any list of “true love” songs, but it’s something many in the age of Tinder booty calls can identify with.  

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54. All the Pretty Colors" by Sturgill Simpson
​In May Sturgill Simpson told his followers on Instagram that if they raised $1 million for a multitude of charities in a matter of two weeks, he would repay their philanthropy with two records this year. His fans lived up to their side of the bargain and in mid-October Simpson released Cuttin’ Grass – Vol. 1 (Butcher Shoppe Sessions, which saw the Grammy-winning Kentuckian re-record many of his best songs from his previous albums in a bluegrass style. Many of my favorite Simpson songs were recorded for this album, including my all-time favorite “Living the Dream” (which topped this yearly list in 2014), but I wanted to feature something new to me and to many of Simpson’s fans – one of the three songs Simpson on the album that he did with his previous band Sunday Valley that are really hard to find these days. My favorite of these threes is “All the Pretty Colors,” which features exquisite lines like: “all the colors are bleeding/where’s ol’ Van Gogh when you need him/I bet you my left ear he can relate.” Simpson got some of the best pickers in the world to play with him on this album and he continues to show he can pretty much do it all and in many different sounds. 

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53. "Clotilda's On Fire" by Shemekia Copeland
One of the great blues tracks of 2020 is “Clotilda’s On Fire,” from Shemekia Copeland’s latest release Uncivil War. The song tells the tale of the last slave ship to smuggle African captives to American shores, long after the practice was outlawed, and how fire was set to the ship after delivering its captive passengers to destroy any evidence of the deed near the shores of the Alabama coast. The wreckage of the ship was just uncovered last year. Copeland sings about how the descendants of Clotilda, after being emancipated at the end of the Civil War, prospered by founding the all-black community of Africatown, just north of Mobile, Ala. It’s a true rags-to-riches story and Copeland absolutely nails the vocal, with some fine guitar playing behind it. 

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52. "Hanging Tree" by Drew Moreland
I’m a sucker for a Western cowboy ballad – you know like the kind Marty Robbins popularized – and Texas country artist Drew Moreland released a good one this year in “Hanging Tree.” The song finds our outlaw narrator, who grew up in a good family with big plans, who went wayward and now finds himself waiting at the hanging tree for his impending execution. There’s some fine mandolin and fiddle on this track, especially the twang of the fiddle at the song’s end that signifies the bottom of the gallows has given way and the rope has dropped. 

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51. "Song for Sam Cooke (Here in America)" by Dion feat. Paul Simon
One of the most touching and heartbreaking songs of 2020 is “Song for Sam Cooke (Here In America)" by Dion on his latest album Blues With Friends. Dion writes about touring the United States in the early ‘60s as one of the nation’s top pop stars with fellow superstar singer and friend Sam Cooke and how it took doing so for him to see things in this country were completely different for a white Italian-American than they were for an African-American. It’s a great tribute to his friend and a good listen for anybody needing an explainer about “white privilege.” Dion is joined by the legendary Paul Simon on the track, who gives the song some terrific harmonies. 

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