Sturgill Simpson Songs, Ranked
In an eight-year time span (2013-2021), Sturgill Simpson gave us five great records, plus two bluegrass albums reinventing songs from his catalog. The Kentucky native and Navy vet has managed to nab Grammy noms in four different genres (Americana, rock, country and bluegrass). Now that Simpson has delivered his promised five original albums and begun to release music under the name Johnny Blue Skies, let’s take a look back at the 10 best songs from the career of one of Americana’s most unpredictable artists.
10) “Life Ain’t Fair and the World Is Mean” (from 2013’s High Top Mountain) – The first track from Simpson’s solo debut serves as a fine introduction to the uncompromising ethos of a relatively unknown songwriter, refuting the assertions of any number of A&R men – “Said your voice might be too genuine/Your song’s a little too sincere.” And while the tune’s twang is straight out of early 70’s left-of-center country, Simpson isn’t shooting to replicate their reputations – “The most outlaw thing that I’ve ever done/Was give a good woman a ring.” His refusal to be pigeonholed as his generation’s Jennings/Haggard/Kristofferson is, ironically, what makes him an outlaw.
9) “Hobo Cartoon” (from 2020’s Cuttin’ Grass – Vol. 2 (Cowboy Arms Sessions)) – Don’t confuse individuality for lack of respect, though. Simpson admired – and maintained friendships with – his musical forbearers. This song, with lyrics penned by Merle Haggard and musically fleshed out by Simpson and his ace bluegrass band (here spotlighting fiddle from Stuart Duncan), pays heed to both the musical heroes and the railroad backgrounds of both men – “Songs from the great Jimmie Rodgers/Hearing ol’ Bing Crosby croon/This is a song of how things used to be/And a script of a hobo cartoon.”
8) “Fastest Horse in Town” (from 2019’s SOUND & FURY) – There’s outlaw, and there’s obstinate. Simpson is a mix of the two, with this sludgy sci-fi record leaning (admirably) toward the latter – a hard left turn from the Grammy-winning A Sailor’s Guide to Earth, it was the album SImpson wanted to make, even if no one was exactly asking for it (which is, you know, what true artists are supposed to do). This album wrapper is Earthly regret (“Oughta be watching the children playing/In the yard I never see I should be mowing today”) buried under a hellscape of guitars.
7) “One in the Saddle, One on the Ground” (from 2021’s The Ballad of Dood & Juanita) – Simpson reenlists his Cuttin’ Grass string band for a concept album that brings to mind John Ford’s The Searchers with a much more likable protagonist. Here, homesteader Dood finds himself chasing down his love, Juanita, after a bandit absconds with her – “Told his son to stay strong/Take care of his sister/”Til Daddy returned with Mama safe and sound.” Dood heads out, “A man and his rifle, a mule, and his hound/One in the saddle, one on the ground…”
6) “Sam” (The Ballad of Dood & Juanita) – And the hound dies. Honestly, a lovely, a cappella tribute to Dood’s pup – “Been many good dog was a friend to a man/But Sam was the greatest one.” But, goddamnit – the dog dies.
5) “Keep It Between the Lines” (from 2016’s A Sailor’s Guide to Earth) – This record was essentially a guide to life from father to son, and this brassy third track urges his son to take a different path than his Navy-bound Dad – “If there’s any doubt, then there is no doubt/The gut don’t lie/And the only word you’ll ever need to know in life is, why” – ask questions, and don’t except easy answers.
4) “Brace for Impact (Live a Little)” (from A Sailor’s Guide to Earth) – The song starts to hint at the grimy rock we’ll hear three years later on SOUND & FURY and includes some filthy slide from longtime guitarist Laur Joamets, as Simpson contemplates his own mortality – “One day you wake up/And this life will be over” – while reminding his son to, yes, live a little “before you go to the great unknown in the sky.”
3) “Life of Sin” (from 2014’s Metamodern Sounds in Country Music) – This twanger from Simpson’s breakthrough record shows the very best of his 70s honky-tonk instincts – plenty of guitar and vocal reverb, while tackling the pitfalls of life as a working musician – “Sex is cheap and talk is overrated/And the boys and me still working on the sound.”
2) “Long White Line” (from Metamodern Sounds in Country Music) – A trucking song that also might be a little bit about cocaine. The singer wants to make bank while forgetting – “Gonna push this rig ‘til I push that girl out of my mind/If somebody wants to know/What’s become of this so-and-so.” Turns out, what’s at the end of that “long white line,” at least on this song, is a jammy squall of guitars.
1) “Call to Arms” (from A Sailor’s Guide to Earth) – In which the Navy-man-turned-ultimate-musical-non-conformist spits on military group think – “Well, they cut off your hair and put a patch on your arm/Strip you of your identity” – and urges his boy to create his own life, expectations be damned – “Well son I hope you don’t grow up/Believing that you’ve got to be a puppet to be a man.” This ferocious album capper of a song, with punchy horns, bluesy guitar wails, and a quiet-to-deafening ou that has Simpson snarl-shouting “The bullshit’s got to go,” is enough to put it at the top of this list. But this song’s performance in 2017 on “Saturday Night Live” has become the stuff of legend; barely contained at the beginning before devolving into guitar-smashing, keyboard-surfing chaos, it remains the best four and a half minutes of music in the long-running show’s history.
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