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The Infinite Possibilities of Sturgill Simpson’s Debut

Reflecting on the 10th anniversary of ‘High Top Mountain’

On May 18, 2023

The most dangerous thing in country music is an artist with nothing to lose. Someone who doesn’t need the Music City Machinery to rev behind them, doesn’t need the co-signs from artists from the ’90s, doesn’t need the fame, fortune and everything that goes with it to feel fulfilled. Doesn’t need to gladhand the radio programmers, doesn’t need to go to every industry party and shmooze like it’s their job. What the outlaws like Waylon, Kris and Willie represented was not so much a genre shift, but a spiritual one: When the suits could no longer tell Waylon his albums couldn’t be songs about how hungover and worn out he was, or that Willie couldn’t make an album of standards, it created an entire vortex for artists to ride on through, following their own muse with nothing to lose.  

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Few artists had less to lose than Sturgill Simpson in 2012 and 2013. He was freshly back in Nashville after spending a few years working on railroads and playing open mics, freshly broken up with his long-running band Sunday Valley and readying his solo debut. He’d made his bones as a railroad man, working a 9-to-5, but his wife encouraged him to give music one last shot, and he was gearing up to take it. Maxing out his funds to the tune of $25,000 — a bunch of which presumably went to hiring session music ringers like Robby Turner (Waylon Jennings) and Hargus “Pig” Robbins (basically every country singer ever) — he wrote and recorded High Top Mountain, an assured, stunning album devoted as much to his family story as it is to telling the tale of a country singer trying to make a living. It wouldn’t top any charts, and wouldn’t launch any hits (at least not in the classic definition of that term). But it did make its money back, and it allowed Simpson to make his next album, and the one after that. He had nothing to lose, and he gained everything, thanks, in no small part, to this 12-song album, celebrating its 10th anniversary with this VMP pressing. 

It’s hard, lo these 10 years, not to frame everything he sings about on High Top Mountain, at least the parts about being a country singer, as some veritable dispatch from Nostradamus, predicting all that came since. The major-label deal that ended in acrimony and an anime film. The protesting outside country music awards shows. The bluegrass reimaginings of his songs, including allusions to getting out of said record deal. Going indie again. But High Top Mountain is not a soothsaying album; it’s an album about possibility. It’s an album about someone needing to get out the songs in their head, regardless of whether or not they can “sell.” It’s a dice roll in the back alley craps game that is life, and Sturgill came up with 7. 

The first line sung by Simpson on High Top Mountain is about the great villains of Nashville, A&R men: “Well that label man said, ‘Son, now can you sing a little bit more clear / Your voice might be too genuine, and your song’s a little too sincere.’” That Simpson sings that line in his trademark scuffed howl brings the point of the record further: He’s aware this album is out of lockstep with modern country, but he doesn’t give a fuck. He’s going to do it his way, since, after all, as the song title says, “Life Ain’t Fair And The World Is Mean.” 

Elsewhere, on “Some Days,” he sings of being tired of getting treated like competition in Nashville, when artists should be fighting to be their best selves. Over sauntering drums, he growls, “What’s a honky gotta do around here to get a little recognition / Start to think I might be worth more to everybody if I was dead,” capturing in two lines the struggle to get noticed out of the bucket of crabs that Nashville often feels like to the people selling their songs there. The album closes with “I’d Have To Be Crazy,” a Steven Fromholz song famous for being played by Willie Nelson on his The Sound in Your Mind album. A ballad about promising a lover you’d never leave them, it opens with the line, “I'd have to be crazy to stop all my singing / And never play music again,” as good as a bookend to the opening line of “Life Ain’t Fair” that exists. 

The album’s best paean to the process of being a country singer is “You Can Have The Crown,” a song that imagines the quotidian existence of the songwriter, as he sits on the couch watching The Dukes of Hazzard and ponders things on eBay that he cannot afford. “Lord, if I could just get me a record deal, I might not have to worry about my next meal,” Simpson sings in the song’s second verse, after promising earlier that he’d sell his soul in a heartbeat if the devil came with a decent contract. It’s one of the finest songs in Simpson’s catalog because it captures his ethos most perfectly: It’s funny, it’s reverent to old styles without being cosplay and it’s a song that feels great to shout along to, as the futility of songwriting can really be transposed onto any life that has dreams unfulfilled. It’s the only Simpson song that can be credibly covered by Post Malone, in other words.  

Those songs, a third of the album, made Sturgill popular with a certain kind of country listener, but they’re not why we’re here, me writing, you reading, 10 years later. It’s the other eight songs that laid the foundation for Simpson. Because he clearly treated High Top Mountain as his moment, his chance to get everything down onto record, before he maybe needed to call it quits, he lays track for everything that came in these last 10 years, setting the template for everything that followed.  

On “Railroad Of Sin” and “Poor Rambler,” we get peeks at his bluegrass past, and the template for his Cuttin’ Grass series from 2020. On “Water In A Well” and “The Storm,” we get previews of what kind of inward, deep ballads he’d perform on Metamodern Sounds in Country Music and A Sailor’s Guide to Earth. On “Sitting Here Without You” and “Time After All” there are the seeds of the brutal efficiency and honky-tonk rock of Sound & Fury, and “Hero” and “Old King Coal” lay the groundwork for the family legacy-focused song cycle of The Ballad of Dood & Juanita. Every artist starts somewhere, and as far as starting moments go, High Top Mountain was a complete one. 

Interviewed shortly after Metamodern Sounds took the world by storm, Simpson seemed to have the prescience that his career would go many different directions, especially after High Top Mountain’s more traditional bend. “I love all kinds of music, but it just so happens that if I sit down with a guitar and open my voice to sing that’s what comes out,” he told FADER in 2014. “That doesn’t mean I ever have to put myself in that sort of self-invented prison of novelty where all I can sing about are these traditional themes. I’m into a lot of different stuff and that’s what came out. That’s where my head was. It might take some people a little by the wayside, or they may never get into it. There’ll be other people that come onboard for everybody that falls off.” 

High Top Mountain certainly leaned traditional, but it also set the precedent that Simpson was not an artist content to coast, was not someone just trying to write the easiest song to ride to the top. He was willing to put in the work, and hire $25,000 worth of studio time and band members to make his vision a reality, and didn’t very much care what happened next. Only that he’d done it. Freedom, as a famous country singer once wrote for Janis Joplin, is just another word for nothing left to lose. The most free performer we’ve had these last 10 years is Simpson, who took a trip to High Top Mountain and never came back down. 

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Andrew Winistorfer

Andrew Winistorfer is Senior Director of Music and Editorial at Vinyl Me, Please, and a writer and editor of their books, 100 Albums You Need in Your Collection and The Best Record Stores in the United States. He’s written Listening Notes for more than 30 VMP releases, co-produced multiple VMP Anthologies, and executive produced the VMP Anthologies The Story of Vanguard, The Story of Willie Nelson, Miles Davis: The Electric Years and The Story of Waylon Jennings. He lives in Saint Paul, Minnesota.

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