The Sturgill Simpson Albums Ranked
Across the eight albums he’s released in the 11 years since 2013, Sturgill Simpson hasn’t really done the same thing twice (well, with one exception to be explained in short order). The insurgent country artist seemed to come out of nowhere to my untrained eye with his first solo album, but it was a somewhat long road to undercutting genre expectations then and now, winding through a former band (Sunday Valley) and a career with Union Pacific Railroad. Simpson has also acted in some great movies like KILLERS OF THE FLOWER MOON (2023). Ultimately, he’s stood out to me as a kind of antidote to the mainstream country sound of today, a status praised by many others and compared to the outlaw country emergence decades ago. But Simpson has also evolved past even that relatively simple designation, as he’s woven other genres, inspirations, and approaches into his twangy origins.
#8 — CUTTIN’ GRASS, VOL. 1: THE BUTCHER SHOPPE SESSIONS (2020)
Favorite track: “Life of Sin”
Re-record projects, by their very nature, are essentially underwhelming to me. There’s rarely something revelatory about a new approach (if it is indeed truly new) to their own old songs from an artist and CUTTIN’ GRASS, VOL. 1: THE BUTCHER SHOPPE SESSIONS is not really an exception. Simpson’s double album bluegrass reinterpretation of some of his best songs, including those written for and with Sunday Valley, is not bad, to be clear. As one of his two most straightforward albums, this record is a pretty joyful ode to a country subgenre. CUTTIN’ GRASS, VOL. 1 does genuinely transform some of Simpson’s songs, but not into something more resonant or necessarily more fun, even as the tone of it is probably more collectively upbeat than anything else he’s put out.
#7 — CUTTIN’ GRASS, VOL. 2: THE COWBOY ARMS SESSIONS (2020)
Favorite track: “Brace for Impact (Live a Little)”
CUTTIN’ GRASS, VOL. 2: THE COWBOY ARMS SESSIONS and its predecessor do kind of feel like “COVID projects,” recorded and released in 2020 as they were. But that perhaps slightly negative term does not eliminate the pleasures of both records. CUTTIN’ GRASS, VOL. 2 reins in the length as a single album and features a tighter selection of past songs, including two Simpson hadn’t previously recorded and ones that deepen the tone that is a bit simpler on VOL. 1. As I promised in my intro, these two releases represent the one time that Simpson has kind of retread the same path, but that might be an unfair statement as they were recorded together and conceived as one project, even if they were released separately and I’m considering them as such here. CUTTIN’ GRASS, VOL. 2 is certainly of a kind with VOL. 1 but it represents a marginal improvement in Simpson’s approach to bluegrass.
#6 — THE BALLAD OF DOOD & JUANITA (2021)
Favorite track: “Sam”
When someone puts out a concept album, I kind of expect an extended length. But THE BALLAD OF DOOD & JUANITA, at 27 minutes long, is Simpson’s shortest album. But this Civil War story of a sharpshooter (Dood) setting out to save his Juanita from the kidnapper outlaw Seamus McClure is still pretty potent. THE BALLAD OF DOOD & JUANITA twangs with Simpson’s bluegrass inspiration, as a Kentuckian creating a story set in Kentucky, but it’s also infused with gospel and a cappella (as in my favorite and somber track “Sam”). The narrative is simple but accented by clever turns of phrase and the “sidekicks,” the mule Shamrock and the dog Sam. THE BALLAD OF DOOD & JUANITA feels a little slight, to its credit in some cases (again, as in “Sam”) but also to its detriment from my perhaps misplaced expectations for Simpson.
#5 — HIGH TOP MOUNTAIN (2013)
Favorite track: “Time After All”
Besides the CUTTIN’ GRASS records, Simpson’s debut HIGH TOP MOUNTAIN is perhaps his most straightforward and upbeat release, at least musically if not always lyrically. But this “back to basics” kind of record isn’t some shallow listen. Layered with a bit of wistfulness, especially in my favorite track “Time After All,” HIGH TOP MOUNTAIN is rich in sound. Listening to it again to prepare for this piece, I was surprised by elements of the composition and production I hadn’t noticed before. I understand how this immediately gained Simpson some attention in the country music sphere, especially listening to some of the biggest hits in the genre in 2013. HIGH TOP MOUNTAIN is better than all of that, and sits comfortably in a movement from Simpson’s similarly offbeat peers, even as he would improve in very short order.
#4 — PASSAGE DU DESIR (2024)
Favorite track: “Right Kind of Dream”
Simpson’s latest album at the time of this writing and the impetus for this piece, PASSAGE DU DESIR wasn’t even technically released under his name. Instead, it’s credited to “Johnny Blue Skies,” as Simpson had promised to no longer release under his own name after five records (the CUTTIN’ GRASS ones apparently don’t count). But it still lists “Sturgill Simpson” as an artist on Spotify, so what is the goal here? In any event, in spite of this nitpicking and generally dismissive tone I’ve just displayed, PASSAGE DU DESIR is great. After the mild successes of Simpson’s “bluegrass run,” this groovy and more eclectic album is reinvigorating. There’s a certain “‘70s-ness” to PASSAGE DU DESIR, perhaps in the production sound of Simpson’s tremendously deep and soulful voice or backing instrumentation that doesn’t fit neatly into country conventions, like strings and plinking piano. The record has a cohesive tone to it but it never settles into a malaise, even as it plays with a more laid-back pace and energy. PASSAGE DU DESIR may or may not be the start of a new career phase for Simpson, as Johnny Blue Skies or as the crafter of a different kind of sound, but as its own work, it’s very rewarding.
#3 — A SAILOR’S GUIDE TO EARTH (2016)
Favorite track: “Brace for Impact (Live a Little)”
I understand Simpson took some issue with his Grammys success in this phase of his career, as A SAILOR’S GUIDE TO EARTH was nominated for Album of the Year and won Best Country Album and he retroactively saw such things as attempted control by his new big record label Atlantic. Regardless of these show biz machinations, this record is big. I don’t mean it’s especially long (it runs 38 minutes), but that its production, influences, and lyrical and tonal themes create a heady brew. Using spacey and ambient soundscapes like he sort of did on his previous album, Simpson creates with A SAILOR’S GUIDE TO EARTH a simultaneously rollicking and somber record that sort of infiltrates my mind on repeat listens. I can’t quite put my finger on it, but the album veers between a sort of detached coolness as on “Brace for Impact (Live a Little),” vague menace, also as on “Brace for Impact” in its extended jam at the end of the song, and earnest love, as a total devotion to Simpson’s family. A SAILOR’S GUIDE TO EARTH isn’t exactly messy, but its eclecticism is a lot to take in at first until the refinement really settles in.
#2 — METAMODERN SOUNDS IN COUNTRY MUSIC (2014)
Favorite track: “Life of Sin”
I’m not really dialed into the opinions of Sturgill-heads, so I can’t write this with a ton of certainty, but my impression is that METAMODERN SOUNDS IN COUNTRY MUSIC is a common favorite for the best album from Simpson. It’s definitely true that this sophomore effort is no slump, as it expands the countercultural leanings of HIGH TOP MOUNTAIN into a full-blown challenge. It’s right there in the title; METAMODERN SOUNDS IN COUNTRY MUSIC seems to take on “country music” as a thematic entity and bring it into a new elevated state. But for all its modernism, and it’s certainly there in some of the more echo-y tracks, part of the record’s appeal is how it channels that outlaw country comparison to great effect, as can be best heard on “Life of Sin.” METAMODERN SOUNDS is just cool but not in the same detached way I clock on A SAILOR’S GUIDE TO EARTH. For a concerted effort to compose something a bit more labyrinthine yet totally accessible as a country/rock/pop fusion, the procession of tracks on the album feel kind of effortless and, well, spiritual. METAMODERN SOUNDS is certainly impressive and Simpson did indeed deserve his wider break because of its achievements.
#1 — SOUND & FURY (2019)
Favorite track: “Mercury in Retrograde”
My strongest sentiments lie with Simpson’s most unconventional album to date, which came after the biggest gap between releases at over three years. SOUND & FURY is a messy collection of hard rock, metal, beach-y pop, and yes, country, anchored by a kind of apocalyptic energy that lifts only slightly for a song like the upbeat and spacey “Mercury in Retrograde.” The album demonstrates Simpson’s incredible songwriting chops better than any other, as he veers to and from genres and totally different vocal and production approaches. SOUND & FURY was also conceived as a visual album; its accompanying anime film of the same name is a fantastic display of grotesquerie and Mad Max-esque imagery. It effectively and cleverly visualizes the menace of most of SOUND & FURY’s tracks. But even just evaluating the record on its own merit, its variances and tone make for an album that thrillingly feels like it’s on the verge of falling apart. That it doesn’t, and indeed consistently surprises and imparts a driving energy, mark SOUND & FURY as a great album beyond easy genre designation and Simpson’s best.
