For nearly 15 years, Sturgill Simpson has been the most interesting man in country music. Part of that involves making albums that don’t sound much like country, like Mutiny After Midnight, his latest effort as Johnny Blue Skies due this Friday. (Though Sturgill leaked the album himself on YouTube for a brief spell.) A self-described “disco hedonism” record, Mutiny After Midnight is a Sturgill Simpson album through and through, twinning lyrics about sex and politics with music that sounds like a cross of the Allman Brothers Band and Chic. It’s the kind of record only he could have made.
Sturgill is one of my favorite artists going right now, and one of my favorite artists to write about. I’ve been tangling with his body of work in print and elsewhere for nearly as long as Sturgill has been making albums. So, I am both thrilled and mortified to rank all the Sturgill albums in order of preference.
Brace for impact, because here comes my list!
8. The Ballad Of Dood And Juanita (2021)
Sturgill Simpson’s discography means a lot to me. I value each album for a different reason. But I have affection for all of them. It’s just that the process of making a list requires that something sits at the bottom. If you are upset that this album is at No. 8 — affects a Johnny Blue Skies-style rhetorical posture — direct your ire at the system of integers that long ago determined that “8” is the lowest of all numbers included here.
Every Sturgill release is, in some sense, a concept record. Sometimes there’s an over-arching theme (fatherhood on A Sailor’s Guide To Earth) or story (whatever the hell is going down on Sound & Fury). But more often it’s about whatever genre experiment is currently on his mind (starting with High Top Mountain, the trad-country record he made for his pawpaw, the “Dood” referenced in The Ballad Of Dood And Juanita). But of all those albums, the one that feels the most like a self-contained movie (or, perhaps more accurately, a novella). It’s also his shortest record, clocking in just at 28 minutes. Though the scant running time shouldn’t be confused for lack of sophistication or ideas.
The Ballad Of Dood And Juantia unfolds like an homage to two adjacent forms that peaked in the 1970s — the Sam Peckinpah-style anti-western, and the “literary” outlaw-country song cycle, specifically Willie Nelson’s epochal Red Headed Stranger. Willie himself guests on Dood And Juanita, adding to the album’s verisimilitude as a perfectly pitched period piece.
Good album! Just less exciting and slighter than all the other albums here.
7. Both Cuttin’ Grass albums (2020)
Upon the release of Dood And Juantia, Simpson talked to Rolling Stone about his long-standing promise to make only five albums, a pledge that dated back to the height of his mainstream acclaim in the mid-2010s. He insisted that he would only be back under a new band guise, a declaration he followed through on upon the release of 2024’s Passage du Desir, his debut as Johnny Blue Skies.
However, his “five albums” promise — which I naturally loved as an adherent of The Five Albums Test — disregard an inconvenient truth: Sturgill had technically put out seven albums at that point. The two releases he was excising from the “five albums” count were volumes one and two of Cuttin’ Grass, released during the pandemic. Now, I understand the logic of not counting these records — they are not “original” albums, but rather compilations of new recordings of old songs done in a bluegrass style.
These are not “full-on” Sturgill records like the others. No one disputes this.
So why am I putting both Cuttin’ Grass albums in the No. 7 spot? Because they nevertheless hold an important place in Sturgill’s creative life as palate cleansers (along with being incredibly fun to put on). In the annals of Sturgill-dom, the scuttled Sound & Fury — which lasted a handful of dates before being shut down by Covid — amounts to the biggest “what if?” of his career. But given how miserable he was heading into those dates (as he confided to me in a 2020 interview), it’s worth pondering whether he would have scuttled the tour even without Covid. For all the bad parts of the lockdown, it was advantageous for Sturgill, who ended up pursuing a much different sound on his own during his forced vacation.
Cuttin’ Grass amounts to a retrenchment I would liken to Bob Dylan retreating to folk music on his early ’90s albums Good As I Been To You and World Gone Wrong, which enabled to recharge his creative juices and recover his lost muse. Given Sturgill’s path since Cuttin’ Grass, those albums feel similarly restorative.
6. Mutiny After Midnight (2026)
The joy of Cuttin’ Grass is that it’s the closest Sturgill — one of the great stage performers of the last 10 years — has come to putting out an official live album. (He told me in 2020 that every show on the Sailor’s Guide tour was taped, though no recordings have yet surfaced. Anyway, thank god for Nugs.)
The main attraction on Mutiny After Midnight is Simpson’s chemistry with his backing band, The Dark Clouds. The focus, smartly, is bottling up the swampy choogle they conjure on stage. (There’s also the promise — nay certainty — that this music will sound even more potent live.) The sound of Mutiny After Midnight is so intoxicating that it nearly makes up for the weaknesses of the songwriting, which are considerable. If Mutiny After Midnight must be counted as one of the most visceral Sturgill albums, it is one of his lesser efforts on a song-by-song basis.
When I reviewed the album last week, I compared it to Midnite Vultures, Beck’s stab of greasy funk laced with hyper-sexual lyrics that frequently ventures into “you can’t be serious” territory. A similar vibe pervades the most “in heat” sections of Mutiny After Midnight, where Sturgill compares himself (favorably!) to Hunter Biden while going one step beyond endorsing threesomes (which, naturally, means stumping for foursomes).
I can’t really take this album seriously, nor can I wipe the huge grin off my face whenever I put it on.
5. High Top Mountain (2013)
On social media right now, as I type this, there is an extremely self-serious fan of Sturgill Simpson that posts under the name “Waylon Jennings’ Gonads” (or something like that) who is very upset that he made an album like Mutiny After Midnight and not an album like his debut, High Top Mountain. This wing of Simpson’s fanbase — let’s just call them the “Waylon Jennings’ Gonads” people — continues to listen to Sturgill just so they can voice their displeasure every time he deviates from a traditionalist country template. Because he made that album first, there’s an inclination to assume that High Top Mountain is his “regular” sound and all the records that came after are his “experiments.” But I don’t think that’s true. High Top Mountain was also an experiment, and that experiment was in “making music Sturgill’s grandfather likes.” Sorry to make another Bob Dylan analogy but: It’s like how he is still classified as a protest singer by a portion of his audience because he wrote songs in the style waaaay at the beginning of his career, even though those tunes represent a tiny of fraction of his overall body of work. Similarly with Simpson, the down-the-middle country music of High Top Mountain is an anomaly in his catalog.
Because I find the “Waylon Jennings’ Gonads” people to be generally insufferable, those negative feelings sometimes rub off on High Top Mountain by association. And that is unfair, because whenever I play it, I’m reminded that this is an incredibly enjoyable honky-tonk record. It’s so good that it’s actually makes me feel empathy for the WJG crowd, because Sturgill honestly is really good at pulling off this style.
The only reason it’s not higher on this list is that — unlike the four records ahead of it, or even the ones before it — I don’t know that High Top Mountain is the kind of album that only Sturgill could have made. No matter the skillful execution, it’s still essentially the sort of throwback genre exercise that many other artists have mounted. After this, he stopped making country records and started making Sturgill Simpson records.
4. A Sailor’s Guide To Earth (2016)
If there is a “regular” or home base sound for Sturgill, it’s not the revivalism of High Top Mountain, it’s some combination of this record and 2019’s Sound & Fury. The latter’s anti-careerist irreverence reflects his worldview, while the stew of southern rock, laidback funky R&B, and intense spiritual introspection cooking on A Sailor’s Guide To Earth points to his bedrock palate. The last two albums, in particular, owe something to A Sailor’s Guide, which is ironic given that the music Sturgill has made under his supposedly divergent Johnny Blue Skies identity most resembles the record that put him at the heart of the music industry.
While Metamodern Sounds teed him up as a media darling, A Sailor’s Guide is where he became a true star, the point where he wowed audiences on Saturday Night Live and vyed for the top awards at the Grammys. It’s also the period when he was the most miserable — he’s long lamented his mental state on the album’s long support tour, when he apparently retreated into chemical dependency amid the cold and oppressively lonely environs of countless hotel rooms on the road. It’s the very state of mind he’s worked to actively avoid ever since.
But the actual music on A Sailor’s Guide — a hearty mix of ’60s soul, ’70s Elvis, and Little Feat — truly seems like the most natural fit for him. And it’s a skeleton key for understanding the whole of his career, starting with the reference to “the dread pirate Johnny Blue Skies” in the liner notes.
3. Passage du Desir (2024)
It’s that very prescient nod to JBS on A Sailor’s Guide that joins his third album with his eighth. Though, again, they’re also linked by how similar they sound. As I wrote in my review of Passage du Desir at the time, “If A Sailor’s Guide was an accidental Grammy-baiting album, this feels like Sturgill’s most “intentional Grammy shit” record imaginable. It is smooth, carefully considered music, and positively yacht-rock-ian.” There are also the obvious jam-band overtones, which Sturgill acknowledged by pointing to his participation in the Dead Ahead Festival with Bob Weir and Mickey Hart as the catalyst for his renewed love for playing live. On the album, this is signified by extra-crunchy, extended guitar vehicles like “Mint Tea” and “One For The Road.”
But it really manifested on the brilliant support tour for Passage, which amounts to the very finest music he’s yet made in his career. Solely as a record, I might slightly prefer A Sailor’s Guide To Earth. But it’s impossible for me to separate my feelings about the Passage du Desir tour from the album. “Not to belabor the point, but he is having a goddamn ball on stage these days,” I wrote at the time. “He’s smiling wide, he’s standing on amps, and he appears intent on destroying every audience standing before him. (The army jacket he donned on stage underlined the ‘joyful warrior’ posture.) The show I saw ended with ‘Call To Arms,’ which at nearly 14 minutes was also the longest number of the night. Every second of that was earned, with Sturgill imploring his band to play harder and louder and faster. Then the band drifted into a space-rock jam, with [guitarist Laur] Joamets sending slide-guitar lines to the outer rings of Saturn. Right when nirvana was about to be achieved, Sturgill steered the song back into ‘harder and louder and faster’ territory, guiding the band to an overpowering climax of sound. It was part Jerry Garcia in 1972, and part the E Street Band on the Darkness On The Edge Of Town tour.”
2. Metamodern Sounds In Country Music (2014)
I was sitting here for a minute trying to come up with an insightful theory about why this album is so central not only to Sturgill’s career but for the entire genre of whatever “Americana” means in 2026. But then I saw this quote from the first piece I ever wrote about Simpson, culled from an interview in the spring of 2014 before a show in Madison, Wisconsin.
“Our generation right now, everybody is caught up on nostalgia, and technology has never been moving faster,” he told in a hotel room just down the road from the concert venue. “You get these weird juxtapositions coming together, so I wanted to do an album that was kind of a roller coaster between nostalgic sentimentality and then contrast it with corporate media fucking killing the world and all that kind of thing. I was like, yeah, Metamodern is kind of like the perfect title.”
That just about sums up things perfectly. If anything, Sturgill was a little ahead of the curve. Particularly the part about “nostalgic sentimentality” and “corporate media fucking killing the world” colliding together to make a shit sandwich of modern culture. I remember those things feeling present in 2014, but they are way more overwhelming a dozen years later. The master stroke of addressing these urgent contemporary matters in the form of a country-rock record that lovingly affects a combination of Merle Haggard and The Notorious Byrd Brothers remains one of his most singularly brilliant ideas, and it’s what makes this such a relevant and, well, metamodern listen all these years later. More than any other record of its kind that I can think of, it captures the sound of being alive in its moment more or less completely.
1. Sound & Fury (2019)
This one, meanwhile, plays like a overture for the oncoming chaos, confusion, disorder, and dissonance of the 2020s. When it came out, a lot of people (including some of his biggest proponents) hated this self-described “sleazy synth-rock dance record.” And yet, now, it’s hard to imagine anyone who still calls themselves a Sturgill fan not absolutely loving this record. It’s like a secret code that gets you admittance into the club.
In the moment, though, it was presented “as a kind of career suicide move,” I wrote in 2019. But “what comes through the speakers is loose, liberated, and deeply pleasurable. Whether he’s emulating the grandeur of David Gilmour on the majestic country-prog ballad ‘All Said And Done’ or burning though the heavy riffing desert rock of the defiant closer ‘Fastest Horse In Town,’ a hybrid of Dwight Yoakam and Queens Of The Stone Age, Simpson sounds like a man doing exactly what he wants, and getting away with it brilliantly.”
That sense of liberation from any lingering forms of country-music orthodoxy is what animates this album, along with Sturgill’s “fury” at any number of subjects — his record label, the music industry at large, the media, the “Waylon Jennings’ Gonads” people, anyone who might not understand his crazy-ass excursions into samurai-cowboy anime, and so on. But the most crucial development, musically, has to be Sturgill stepping out as one of our great modern guitar heroes. Who knew that setting his songs against Giorgio Moroder-style disco grooves would unlock his inner Billy Gibbons?
Anyone who has heard Eliminator, I suppose. Certainly, Sturgill studied that record and carried the lessons forward in his career. While his subsequent records sound warmer and less synthetic, Sound & Fury nevertheless informs the spirit of everything he’s done ever since. His work is sleazier, dancier, and all the better for it.
