It’s no stretch to say that reigning ACM Entertainer of the Year, Chris Stapleton, has already achieved legend status in the genre. The Tennessee Whiskey singer has already won 10 Grammys, including two for his latest #1 hit, White Horse, earlier in the month.
With that being said, I don’t think that Stapleton has released a bad or even a mediocre song over the course of his career, meaning that this list felt nearly impossible to compile.
Without further ado, here are all 63 Chris Stapleton’s songs ranked “worst” to best.
63. Friendship
62. South Dakota
61. Old Friends
60. Hillbilly Blood
59. Crosswind
58. Whiskey Sunrise
57. Without Your Love
56. What Am I Gonna Do
55. Watch You Burn
54. The Fire
53. Was It 26
52. Hard Livin’
51. Nothing Else Matters
50. Outlaw State of Mind
49. Nobody’s Lonely Tonight
48. Mountains in My Mind
47. It Takes A Woman
46. Last Thing I Needed, First Thing This Morning
45. Death Row
44. Might As Well Get Stoned
43. Drunkard’s Prayer
42. I’m A Ram
41. Tryin’ to Untangle My Mind
40. Devil Always Made Me Think Twice
39. Joy of My Life
38. Weight Of Your World
37. When I’m With You
36. Worry B Gone
35. The Bottom
34. The Day I Die
33. Arkansas
32. Loving You On My Mind
31. Up to No Good Livin’
30. Sometimes I Cry
29. Trust
28. Them Stems
27. Nobody to Blame
26. The Devil Named Music
25. I Was Wrong
24. Higher
23. Second One to Know
22. Broken Halos
21. More of You
20. Millionaire
19. Starting Over
18. Think I’m In Love With You
17. White Horse
16. When the Stars Come Out
15. Daddy Doesn’t Pray Anymore
14. Whiskey and You
13. A Simple Song
12. Nashville, TN
11. Midnight Train to Memphis
10. Tennessee Whiskey
Coming in at #10 is none other than Stapleton’s 14x platinum cover of David Allan Coe’s Tennessee Whiskey. Sure, you can argue this song is the most over-played country song of the 21st century, but that doesn’t take away from the magic present in this cover.
Like all of Stapleton’s songs, his vocals are simply off-the-charts here. Each and every single run on the track is just as smooth as the titular liquor, resulting in Stapleton’s cover to be the definitive version of the song.
9. You Should Probably Leave
You Should Probably Leave hits the ground running from the first note with that slick, bluesy electric guitar lick, resulting in one of the easiest-to-recognize intros in the past few years.
To me, Stapleton is in his sweet spot when he is blending his country and blues sensibilities, and this track is a shining example of it. The production is off the charts here in a very subtle way. His voice has so much soul, and the guitarwork has a distinct presence to it. The track could have easily had one overshadow the other, but the masterful mix allows both to shine through equally.
8. Scarecrow In the Garden
I’ve always found Scarecrow In the Garden to be Stapleton’s most underrated song in his deep discography. There’s something so different compared to his discography here, borrowing gothic elements from Irish/Celtic folk throughout.
There’s a tangible amount of darkness and dread throughout the track despite it being a mid-tempo song. The way Stapleton vaguely describes the titular scarecrow that “looks like Lucifer” really lets your mind wander and conjure up what it could possibly look like.
Like any effective horror story, Stapleton leaves it up for interpretation, leaving you to wonder what horrors could possibly be hiding in the garden. He ends the song with a perfect, open-ended note, making you ponder the fate of the narrator.
7. Parachute
One of Stapleton’s early hits still remains one of his best to this day. Like You Should Probably Leave, Parachute also hits the ground running with one of the best intros you’ll hear from any country song.
The electric guitar layered with the mandolin sounds absolutely incredible, paving the way to a moody first verse that builds to one of Stapleton’s patented big choruses.
Lyrically, I would say that there are plenty of Stapleton songs that are stronger, but the instrumentation coupled with his gritty vocals make Parachute a delight to listen to.
6. What Are You Listening To?
Stapleton’s debut single from all the back in 2013 remains one of his best songs to date. It’s one of the most fresh takes on missing your ex that I’ve heard. I absolutely adore the way that he frames the very stereotypical song archetype of missing your ex through the lens of wondering what she’s listening to.
I love the way that he ultimately tries to hide his wondering where she is by guessing what she’s listening to. It’s like he’s trying to suppress his feelings of loneliness and abandonment through his love of music.
What Are You Listening To is an expertly penned track by Stapleton and Lee Thomas Miller and proves that familiar country song tropes can be elevated through clever writing.
5. Traveller
The title track of Stapleton’s legendary debut album perfectly sets the stage for one of the greatest country records of all time. Traveller is simply country gold, filled to the brim with steel guitar throughout. It’s one of Stapleton’s most reserved songs from a vocal standpoint, but it fits the song’s tone perfectly.
The track is one of the best travel songs in country music, right up there with Willie Nelson’s On the Road Again, Johnny Cash’s I’ve Been Everywhere and George Strait’s Amarillo by Morning. It’s a must-have on any road trip playlist.
4. Cold
Cold might very well be Stapleton’s greatest vocal performance to date. While he might not be hitting the ridiculous notes that he does on Higher or hitting those iconic growls on songs like Midnight Train to Memphis, Cold is easily one of his most soulful performances.
The orchestral nature of this song coupled with the piano gives it a unique identity compared to the rest of his discography, resulting in one of the most brooding, raw songs he’s released to date.
3. Fire Away
If there was any doubt that Stapleton could deliver some of the most brutal songs you’ve ever heard, Fire Away puts those doubts to rest. There’s such a tangible sense of apathy and desperation throughout the track.
Stapleton paints a picture of an incredibly toxic relationship throughout Cold and juxtaposes it with a desperate feeling of being wanted. No lyric encapsulates this better than, “Your love might be my damnation, but I’ll cry to my grave.” It’s simply one of the most brutal lyrics ever penned in a country song.
2. Either Way
Another contender for best vocal performance by Stapleton is none other than Either Way. If you’re looking for an absolutely brutal depiction of a broken relationship, this track is one of the best depictions of one.
The entire chorus is an absolute masterclass from Stapleton from both a lyrical and vocal perspective. The vocal runs throughout are nothing short of jaw-dropping. The way he hits the first three lines of the chorus with so much strength and then delicately delivers, “But I won’t love you either way.“ is one of my favorite moments in any country song ever.
1. Maggie’s Song
If you want a song that can make you cry each and every time you listen to it, look no further than Maggie’s Song. Depicting the life and eventual death of Stapleton’s dog, Maggie, the track is sure to hit home for any animal lover.
Sure, it might not have the raw emotion vocally of Either Way or Cold, but the storytelling present in Maggie’s Song is fantastic. As someone who’s owned dogs throughout my life, this song is one of the few that gets a little misty-eyed nearly every time I listen to it.
Even putting aside the personal connection to the song as a dog owner, Maggie’s Song is exactly what a country song should be: one that is about the mundane and relatable. It’s a simple song about how much Stapleton loved his dog, nothing more, nothing less. Yet it still delivers a moving story due to his beautiful songwriting throughout.