As Chris Stapleton is about to release his long awaited fourth album, Starting Over, we decided to go through his discography — his entire discography — to figure out what his best songs are. So we pulled from his first three albums, plus the songs that we’ve heard, so far, from Starting Over. But we also reached back to his old rock band, the Jompson Brothers, and his ex-bluegrass band, the Steeldrivers. We also dove into his career as a songwriter for other artists, and pulled some of those songs, as well. So this list collects songs that were either written, or sung, by Chris (or both). Of course, once we hear the rest of the new album, we’ll probably have to update the list!
40. “Tryin’ To Untangle My Mind” – ‘From A Room: Vol. 2’ (2017)
ShareAren’t we all? Here, Stapleton sings about -- we presume -- his wilder, younger days. “Well I drank a lot of whiskey in my time/And I've held a lot of women that were fine/And I made a little money, I blew every dime/Tryin' to untangle my mind.” As a presumably wealthy, family man these days, it seems he’s mostly untangled.
39. “Crash And Burn” – Thomas Rhett – ‘Tangled Up’ (2015)
ShareCo-written by Stapleton and Jesse Frasure. Frasure said that the song came out of sessions where they were trying to write Motown-like songs, with artists like Bruno Mars in mind. Apparently, Rhett was kind of nervous about singing the song after hearing Stapleton sing it on the demo. But the song, like so many of Stapleton’s, translates really well to different singers and different formats.
38. “Say Something” – Justin Timberlake featuring Chris Stapleton – ‘Man Of The Woods’ (2018)
ShareWe’d be remiss not to include a Timberlake collaboration here; after all, it was Stapleton and Timberlake’s performance of “Tennessee Whiskey” and “Drink You Away” at the 2015 CMAs that launched Stapleton to national stardom. And their collaboration on Timberlake’s 2018 country-leaning album was a high point for both artists.
37. “Amanda” – Chris Stapleton and Morgane Stapleton – ‘Gentle Giants: The Songs of Don Williams” (2017)
ShareThis live recording is just Chris singing and playing his acoustic and Morgane, Chris’s wife and bandmate, singing along, paying tribute to Don Williams. Although Stapleton’s shows with his band are legendary, it would be interesting to see Chris and Morgane tour as a duo one day.
36. “Front Porch Thing” – Little Big Town – ‘Tornado’ (2013)
SharePhillip Sweet sings lead on here, leading Little Big Town through an upbeat party stomper. Stapleton’s always-prominent blues influence comes out in the lyrics: “Work's been slow, money's been tight/But that's alright, honey, that's alright/Sometimes you won't, but sometimes you will/And when she do what she do, it's a doggone thrill.”
35. “Arkansas” – ‘Starting Over’ (2020)
ShareA rocker that was co-written by Chris Stapleton and Mike Campbell, the guitarist from Tom Petty & The Heartbreakers, it’s a nice union of two great six-stringers. Stapleton has cited not only Petty, but also Campbell, as a huge influence.
34. “Gonna Come Back As A Country Song” – Alan Jackson – ‘Thirty Miles West’ (2012)
ShareCo-written by Stapleton and Terry McBride, it shows Stapleton’s sense of humor: “Let me just say for the sake of conversation /If it's hard to think as reincarnation /But don't you go crying for me when I'm gone /Told them I'm gonna come back as a country song.”
33. “Hey Girl” – The Jompson Brothers – ‘The Jompson Brothers’ (2010)
ShareThose who were surprised to hear Chris Stapleton playing a straight up hard rock song, “Blow” (with Ed Sheeran and Bruno Mars, of all people) clearly weren’t familiar with his short-lived rock band, the Jompson Brothers, who put out one self-titled album in 2010, after he left the bluegrass group the Steeldrivers. “Hey Girl” is a pretty timeless breakup jam with pretty simple lyrics: “Hey, Girl! I want you to know/I'm gonna miss you so much if you go/And, Hey, Girl! I tell you no lie/Something deep inside of me's going to die.” So, they weren’t Stapleton’s best lyrics, but they’re definitely fun to rock out to.
32. “Tell Me When It’s Over” – Sheryl Crow featuring Chris Stapleton – ‘Threads’ (2019)
ShareStapleton and Crow previously wrote “Homesick” for Crow’s 2013 country album, ‘Feels Like Home,’ but this song, which they also co-wrote, was their first duet on a studio album. “Tell Me When It’s Over” is like an edgier ‘70s R&B hit. Had Stapleton and Crow’s 2020 tour gone on as scheduled, it would have been cool to see the duo singing this one.
31. “If The Devil Don’t Want Me” – Ashley Monroe – ‘The Blade’ (2015)
ShareCo-written by Stapleton, Monroe and Jessi Alexander, it’s a classic country waltz, and one of the saddest ones you’ll ever hear. The narrator has been dumped, and although she knows that her ex- (“the Devil”) was terrible, she wants him back. “I'm at rock bottom with a smoke and a sin/When the party is over, then I'm lonely again.”
30. “Blow” – Ed Sheeran featuring Chris Stapleton and Bruno Mars – “No. 6 Collaborations Project” (2019)
ShareRock music doesn’t crank out guitar heroes like it used to, and hard rock bands don’t produce many classic party jams anymore, either. Enter Ed Sheeran, Chris Stapleton and Bruno Mars with this gem, showing how much fun it is to rock out. Co-written by Sheeran and Stapleton, among others, and produced by Mars, it makes you wish that this trio did a few more jams together.
29. “Them Stems” – ‘From A Room: Volume 1’ (2017)
ShareA mid-tempo rocker about running out of a certain recreational substance. Perhaps you’ve been there!
28. “Death Row” – ‘From A Room: Volume 1’ (2017)
ShareA straight-up slow-burn blues song about being on, well, death row. The lyrics are as dark as Johnny Cash at his most desolate: “When it's time for my last request/Tell my mama that I did my best/Tell my baby that I love her so.”
27. “The Reckless Side Of Me” – The Steeldrivers – ‘Reckless’ (2010)
ShareThe opening track from the Steeldrivers’ second album, and their final album with Stapleton. His lyrics, as is so often the case, are poetic yet easily relatable: “There's two angels sittin’ on my shoulders/All they ever do is disagree/One sits on the side of rhyme and reason/The other on the reckless side of me.”
26. “Was It 26” – ‘Traveller’ (2015)
ShareStapleton is such a good songwriter, it’s surprising that he often covers other people’s songs. But as a singer, he’s a great interpreter: exhibit A :his cover of the Charlie Daniels Band’s “Was It 26.” In it, the narrator tries to recall what happened while he was 25… or was it 26.
25. “Daddy Doesn’t Pray Anymore” – ‘Traveller’ (2015)
ShareA somber acoustic song featuring the mournful harmonica of Mickey Raphael (from Willie Nelson’s band). The narrator in the song watches as his father loses his belief in God; the son, however, never seems to lose faith.
24. “Nobody To Blame” – ‘Traveller’ (2015)
ShareStapleton’s first top 10 country single as an artist is an epic breakup jam. His ex- tore their wedding photograph in half, she puts his guns in hock, poured his whiskey down the drain, burned his guitars, broke his fishing rods, threw his clothes in the yard and then changed the locks. She even drove his hot rod into a pond. You’d think that would make most guys angry. But as Stapleton sings, “I got nobody to blame but me.”
23. “Drinkin’ Dark Whiskey” – The Steeldrivers – ‘The Steeldrivers’ (2008)
Share“Drinking dark whiskey/Telling white lies/One leads to another/On a Saturday night.” You know how it goes! Stapleton helpfully notes, “When the bottle’s talking/Be careful what he might say/It talks in the dark/Like it never would in the day.” You’ve been warned!
22. “There’s More Where That Came From” – Lee Ann Womack – ‘There’s More Where That Came From’ (2005)
ShareA classic country cheating waltz. The narrator laments over the fact that she’s cheated. As she lays and/or lies in bed and begs the Lord to get cheating off of her mind, “He'll call to say that he sure had fun/Just so I know/There's more where that came from.”
21. “You’ve Got To Hide Your Love Away” – Chris Stapleton, Kris Kristofferson and Willie Nelson – ‘Imagine: John Lennon 75th Birthday Concert’ (2019)
ShareStapleton covers a Beatles classic, backed by two country legends at a 2015 tribute concert. At that point, the older rock audience wasn’t necessarily familiar with Stapleton, but many were asking “Who *was* that guy?” Stapleton also performed “Don’t Let Me Down” with Sheryl Crow and Killers frontman Brandon Flowers.
20. “Nobody’s Fool” – Miranda Lambert – ‘Four The Record’ (2011)
ShareMost post breakup songs are from the perspective of the dumped, and Stapleton has certainly written some of those. But on “Nobody’s Fool,” the narrator watches an ex- walk into the bar: “Day I left is my only regret/And now it's become his biggest thrill.” When her friends ask about him, Lambert sings, “I'll just say, ‘He's nobody’/And me, well, I'm nobody's fool.” But she doesn’t sound so sure about it.
19. “Last Thing I Needed, First Thing This Morning” – ‘From A Room: Volume 1’ (2017)
ShareYou gotta hand it to Stapleton, he doesn't blink when it comes to recording country classics. This song is an iconic Willie Nelson hit, and Stapleton even uses Willie’s harmonica player, Mickey Raphael, on this song! But like other great song interpreters, from Wille to Aretha Franklin to Ray Charles, when Stapleton sings a song, it’s *his* song.
18. “Outlaw State Of Mind” – ‘Traveller’ (2015)
ShareOver 40 years ago, the great Waylon Jennings asked, “Don’t You Think This Outlaw Bit’s Done Got Out Of Hand?” He wasn’t wrong, to ask. But Stapleton isn’t wrong, either, when he points out that being an outlaw is just a state of mind.
17. “Might As Well Get Stoned” – ‘Traveller’ (2016)
Share“Since my whiskey’s gone, I might as well get stoned,” Stapleton sings on this jam. The guy got kicked out of his house by his ex-, and then he watches the news, where he sees the hell that soldiers, and their families at home, go through. We are not advocating getting stoned, but we’re not judging him for it either.
16. “Drink A Beer” – Luke Bryan – ‘Crash My Party’ (2013)
ShareIt’s one of Stapleton’s most devastating songs: it’s about the unexpected loss of someone close: it could be a family member, a friend or a lover. Bryan, who had lost both of his siblings, delivers the song absolutely perfectly.
15. Blue Side Of The Mountain – The Steeldrivers – ‘The Steeldrivers’ (2008)
ShareSurely, there aren’t too many bluegrass classics written since 2000, but this would certainly be one of them. This song, which kicked off the Steeldrivers’ debut LP, feels like it could have been written and recorded five or six decades earlier.
14. “I Want Love” – ‘Restoration: The Songs of Elton John and Bernie Taupin’ (2018)
ShareProbably Elton’s best song of this millennium, the lyrics reflect Taupin’s sorrow after going through a third divorce. Happily, Stapleton hasn’t been through that, but he still delivers the song perfectly.
13. “Starting Over” – ‘Starting Over’ (2020)
ShareAn honest look at a relationship, likely based on Chris and Morgane Stapleton. He admits, “This might not be an easy time/There's rivers to cross and hills to climb/Some days we might fall apart/And some nights might feel cold and dark.” But through all of the difficulties of a long term relationship, “Wherever we are is where I wanna be.”
12. “I Was Wrong” – ‘From A Room: Volume 1’ (2017)
ShareAnother song that sounds like it could have been an R&B hit in the ‘70s, with another singer (and quieter guitar).
11. “The Devil Named Music” – ‘Traveller’ (2015)
ShareAs good of a “road song” as Bob Seger’s “Turn The Page,” but coming from an older perspective. “Sometimes I'm drunk/And sometimes I'm stoned/And yes, I get tired of being alone/I miss my son/And I miss my wife/But the devil named music is taking my life.” Surely every touring musician and crew member in any genre of music can identify.
10. “Whiskey And You” – ‘Traveller’ (2015)
ShareThis solo acoustic lament starts out with Stapleton in full-on heartbreak mode: “There's a bottle on the dresser by your ring/And it's empty so right now I don't feel a thing/I'll be hurting when I wake up on the floor.” Of course, he notes that he can pick up more whiskey whenever he wants. “But your forgiveness/ Well, that's something I can't buy.”
9. “Midnight Train To Memphis” – ‘From A Room: Volume 2’ (2017)
ShareOriginally a bluegrass jam from his days in the Steeldrivers, Stapleton revisited the song as a hard-driving rocker for his 2017 album, ‘From A Room: Volume 2.’ The narrator here is sentenced to 40 days in jail, and notes that the 39th day is the hardest.
8. “If It Hadn’t Been For Love” – The Steeldrivers – ‘The Steeldrivers’ (2008)
ShareWhile many Stapleton songs end up on albums by other country singers, this one was later covered by Adele. Apparently, her bus driver turned her on to the song and she recorded it as a bonus track for her '21' album.
7. “When The Stars Come Out” – ‘Traveller’ (2015)
ShareStapleton co-wrote this one with Dan Wilson of alternative rock band Semisonic (you might know their big hit, “Closing Time”). It’s a moving tale of a couple leaving their small town for the city lights. They’re “running on hope and a tank of gas,” and we never really find out if they find what they were looking for. But you get the impression that, at least they’ got close: “ I got a feeling tonight might be the night/Yeah, tonight might be the night.”
6. “Millionaire” – ‘From A Room: Volume 2’ (2017)
ShareThe opening track from ‘From A Room: Volume 2,’ it’s a cover of a song written by country singer/songwriter Kevin Welch which was recorded by soul legend Solomon Burke in 2006 (it’s worth seeking that version out too, BTW). Stapleton more than does the song justice, and it sounds like something he might have written.
5. “Tennessee Whiskey” – ‘Traveller’ (2015)
ShareAgain, Stapleton isn’t shy about taking on country classics: this one, co-written by Dean Dillon and Linda Hargrove, was first recorded by David Allan Coe and later by George Jones. But as always, Stapleton made it his own and one day when his “greatest hits” album is compiled, this is sure to make the tracklisting.
4. “Second One To Know” – ‘From A Room: Volume 1’ (2017)
ShareAs we’ve established, Stapleton has written some of the best country songs of all time. But with songs like this, you realize that if he was around in the ‘70s or ‘80s, he could have had a great side gig writing for rock bands like ZZ Top or Lynyrd Skynyrd.
3. “Traveller” – ‘Traveller’ (2015)
ShareThe title track and lead song from his solo debut, Stapleton wrote this one by himself. Some people just don’t fit in, and they can’t settle down. But just when you think that the song is about being alone, he flips the script a bit: “Somebody else will have to feel this wrong/ Somebody else will have to sing this song/Somebody else will have to sing along.” There are *other* travellers like you out there, too! And when Stapleton tours again, you’ll sing along with a few thousand of them.
2. “Broken Halos” – ‘From A Room: Volume 1’ (2017)
ShareWas ‘Traveller’ a flash in the pan? “Broken Halos,” the lead track and first single from the follow-up, quickly shushed anyone who doubted that Stapleton had more classics in him. Like “Drink A Beer,” this song sadly recalls a friend who left this earth too early.
1. “Fire Away” – ‘Traveler’ (2015)
ShareA love song, but the kind you can only write when you’ve been in a relationship for a while; it’s when you’re at a point in your relationship where it’s strong enough to endure disagreements and fights. Some of Stapleton’s songs see him looking at his mistakes and realizing that he deserves his fate; he’s earned his loneliness, it serves him right. But here, he’s in a relationship that will last; they’re in it for the long haul. This song acknowledges that that road can be bumpy.
