Is The Latest Sturgill Simpson Album Also The Last? An Investigation

In 2017, Sturgill Simpson made a post on Instagram that laid out the rest of his career. After quoting the chorus of Kris Kristofferson’s “The Pilgrim: Chapter 33” — in which the legendary troubadour sings about “a walking contradiction, partly truth and partly fiction” — Simpson wrote that “my entire ‘country music career’ is a character based performance art piece in the form of five sequential concept albums all following the traditional Christian narrative of the journey of the human soul.”

This was heady stuff! At the time, Simpson had released only three albums. His most recent, A Sailor’s Guide To Earth, had been nominated for an Album Of The Year Grammy earlier that year. He was in his prime, and appeared to be rising even higher. It was, in other words, a strange time to be hinting that your quote, country music career, end quote, might soon be over.

But the Instagram post didn’t come completely out of the blue. Simpson had suggested for years in various interviews — most notably on The Joe Rogan Experience in 2014 — that he was ultimately only going to make five LPs. While Simpson quickly deleted his Instagram post, he reiterated his five albums promise one week later while busking outside of the 2017 Country Music Awards. During an informal press conference, he offered up a detailed sketch of how each album fit into his so-called “Christian narrative”:

Yes. I’m only making five albums. And they all do serve a cohesive narrative of a life journey of a human soul from a traditional Western perspective. So High Top Mountain was a seminal album or a past life, you can’t go home. Metamodern Sounds in Country Music was ethereal, literally like the soul’s journey through space. A Sailor’s Guide To Earth represents birth, and life lessons learning them. The next one is going to be about life and sin. We’re literally going to go to hell. And the fifth one will be returning to the light. Absolution.

What nobody beyond Simpson’s inner circle knew at the time is that he had already recorded the bulk of his fourth record, Sound And Fury, which finally came out in the fall of 2019. That caustic and hard-rocking album did indeed prove to be about “literally going to hell,” which reflected Simpson’s self-described “miserable” headspace in 2017, when he achieved his greatest mainstream exposure yet while also feeling extreme weariness from an exhaustive tour schedule. These factors — along with being waylaid by a sinus surgery and mourning the death of his beloved grandfather, Lawrence Gray “Dood” Fraley — fed into the extreme negative mojo of Sound And Fury.

But Simpson’s fantasies about a finite, five albums-only career can’t only be attributed to a temporary funk. According to a Rolling Stone profile posted last week upon the release of Simpson’s latest record, The Ballad Of Dood And Juanita, he insisted again that he’s stopping at five Sturgill Simpson albums. “This is the last Sturgill record,” he told the magazine. “I always said there would be five, and I wondered if I’d go back on that. But it really has cemented every step of the way how much I don’t want to carry all that weight.”

So … is this it? Is the reigning outlaw country singer of our time going to actually retire in the prime of his career? If it is it, what are we to make of the five albums he’s made and how they fit together? (Actually, he’s made seven — more on that in a moment.) Is this five-album arc an incredible called shot on Sturgill’s part, or just plain weird and even misguided?

For starters, it’s worth mentioning that Simpson gave himself an out in that Rolling Stone interview. “Going forward, I’d like to form a proper band with some people who I really love and respect musically, and be a part of something truly democratic in terms of creativity,” he said. “Not having to stand up there behind my name would allow me to be even more vulnerable, in a way.” So, he’s not done done. He’s just done making music in which “Sturgill Simpson” is the predominant brand … maybe. (At the 2017 CMAs, he floated the tantalizing possibility of a Highwayman-like supergroup with Jason Isbell, Chris Stapleton, and Margo Price. I’d be very curious to find out if that is still on the table.)

As a fan of both Sturgill and five-album arcs, I love that he’s been pushing this “‘Christian narrative” concept for his catalogue, especially since it appears that he’s not actually retiring. I love it so much that I’m willing to overlook the obvious flaws in Simpson’s logic, starting with the fact that he’s conveniently leaving off the two volumes of Cuttin’ Grass records he put out in 2020. (Which I think is justified, given that those albums consist of old material reworked in a bluegrass style. They function essentially as greatest hits records.) I’m also skeptical that Simpson had the foresight to truly map out his discography with such precision. For instance, did he really know that Covid would kill the 52-date Sound And Fury tour, therefore alleviating his professional angst and leading him to work with the crack bluegrass pickers who back him on the Cuttin’ Grass records and his concluding “absolution” LP, The Ballad Of Dood And Juanita? Is this a country singer or Nostradamus?

Let’s set all that aside. The same premeditation about his art and career that has annoyed some critics — particularly in light of the divisive Sound And Fury — has endeared Simpson to me. And it has also endeared him to his most loyal fans, who have written insanely detailed and deeply fascinating Reddit posts about how his catalogue parallels the five stages of mysticism.

I wouldn’t go as far as to call his career “performance art,” but the overtly conceptual aspect of Simpson’s work puts him closer to self-conscious pop superstars like Kanye West and Frank Ocean than anyone in the Americana sphere. It’s a big reason why he’s more interesting than almost all his peers; he’s not merely presenting himself as an “earnest” master of “authentic” music, he lets you know that he may in fact be playing a character. Whether he actually plotted his career out well in advance or improvised the particulars on the fly in accordance with the ups and downs of career is irrelevant. The fact is that you can look at his albums, including the new Dood, and see a through-line that more or less does tell a redemption story … if that’s what you want to see.

While Simpson posited his proposed discography as “five sequential concept albums” in that deleted Instagram post, I would argue that (aside from Dood And Juanita) he operates mainly in song cycles. His previous records don’t tell stories as much as riff on a central idea. High Top Mountain is the “nostalgist” record. Metamodern Sounds is the “subverting nostalgia with psychedelics” record. A Sailor’s Guide is the “subverting psychedelics with fatherhood” record. Sound And Fury is the “subvert my entire damn career” record. Then you have the Cuttin’ Grass records as palate cleansers. (Carrying over the “Christian narrative” metaphor, perhaps these albums can be likened to purgatory between hell and heaven.)

And now comes The Ballad Of Dood And Juanita, his first real concept record and a culmination for his catalogue, in which you can hear elements of all the other albums come together in one 28-minute package. It’s traditional but subversive, equal parts witty and melancholy, with a feeling of peace leavened with an undercurrent of violence. It’s his Once Upon A Time In Hollywood — both an expertly rendered homage to Simpson’s old reference points in ’60s and ’70s country and an elegiac summation of the themes and ideas he’s embedded throughout his work.

It also feels cyclical with how he started. Simpson has said that he made his traditionalist 2013 debut High Top Mountain to please his grandfather, a hardcore “classic” country fan and the very same “Dood” who is saluted on Dood And Juanita. (Juanita is the name of Simpson’s real-life grandmother.) The new record is precisely the sort of music that fans of High Top Mountain have likely been waiting for him to make again. But it’s also more iconoclastic and cinematic than the debut, following a trend in which film has played an increasingly large role in Simpson’s career. (His part in Martin Scorsese’s forthcoming movie marks a new peak in his acting career.)

A tale of love and revenge that crosses a Sergio Leone-style story with Coen Brothers-like eccentricity, Dood And Juanita practically is a film for the ears, with a plainly told story involving cold-blooded killers, a heart-rending romance set to Latin-tinged guitar licks played by none other than Willie Nelson, and a very sweet and very dead hound dog. If this is the end of Sturgill Simpson as we know it, The Ballad Of Dood And Juanita is an appropriate closing statement.

Of course, this likely is the end of just this part of his career. And I think it will be worth regarding these five albums as a discrete section of his discography, however it may take shape from here. (Also, for the record: I think he passes the Five Albums Test with The Ballad Of Dood And Juanita.) Then again, it’s equally likely that Simpson will change his mind and knock out a pedal steel-accented prog-rock album under the Sturgill Simpson banner by Thanksgiving. I admire Sturgill, but I don’t exactly trust him. I do appreciate, however, that he remains unpredictable, even if he claims that he’s told us what he’s up to all along.

The Ballad Of Dood And Juanita is out now via High Top Mountain Records. Get it here.