How Sturgill Simpson Went From Playing Bars In Obscurity To The Grammys In Just Four Years

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In April of 2014, I met a little-known 35-year-old country singer in a hotel room in downtown Madison, Wisconsin. We had arranged an interview after I became obsessed with his latest album, a rootsy psychedelic song cycle called Metamodern Sounds in Country Music, which was due to be released the following month. His publicist said I could I meet up with him before he was scheduled to play for about 50 people at a bar down the street.

Fortunately, he was feeling unusually talkative, and the interview lasted for about an hour. It’s still one of my favorite conversations I’ve ever had with a musician. We discussed his background, which was almost too good to be true for a country singer: His early twenties were misspent in his native state of Kentucky, he told me, playing in local bands and working “odd jobs — really disconnected, disenchanted, a lot of substance abuse.” He moved to Nashville in 2005 to launch a music career, but gave up nine months later “because pop-country was just at its peak saturation” and he couldn’t find anyone to play with.

After that, he and his girlfriend packed up and left the south, relocating to Salt Lake City. He went to work for the Union Pacific Railroad, trading a life of singing about trains for a career as a conductor and engineer. For a while, he loved it. Then he “screwed around and took a management position,” he said, which made him responsible for the trains running on time. If the trains were two minutes late, “a bunch of white-collar a**holes that I’ll never meet” from the railroad would call up and scream at him. Life on the rails soon soured.

As a stress reliever, he started gigging around Salt Lake City — actually, his girlfriend would book the shows without telling him. She would lure him out for a date night, and “when we get there, my guitar’s in the trunk, and I’m playing a show,” he recalled. By now he was in his early thirties, and his partner was encouraging him to take one last stab at living his dream. So, in 2010, Sturgill Simpson and his girlfriend (now wife) Sarah gave it another go on Music Row.

Here comes the “… and the rest is history” part: In 2013, Simpson put out his debut, High Top Mountain, a traditional country album dedicated to his grandfather. Metamodern Sounds, meanwhile, was more in Simpson’s wheelhouse, melding his classicist musical leanings with musings about drugs, aliens, and quantum physics.

Back in that Wisconsin hotel room three years ago, I remember Simpson looking out the window and wondering whether he had already achieved what he set out to do. Metamodern Sounds was gaining buzz in the music press, but Simpson was more concerned with the impending birth of his son that June. Against the wishes of his management, Simpson was planning to stay off the road for a few months right as his album was coming out, in order to be with his wife and new baby. If that hurt his fledgling career, so be it.

“If I have to give it up and get a job next year or something, I’ll feel OK with that, because I’ve made two albums that I always wanted to make and feel very proud about,” Simpson told me. “I got to play the Opry and my grandparents were all there, so I don’t really know what else I would have to achieve in terms of my own idea of success. I’m not really looking for a major-label deal — to see myself on CMT doing all that, I know what comes with that.”

Of course, Simpson still had plenty more to achieve. In 2015, in the wake of Metamodern Sounds becoming a major critical hit and Simpson building an increasingly strong business as a touring act, he landed that major-label deal that he hadn’t planned on looking for with Atlantic Records. The following year, Simpson released his Atlantic debut and third LP overall, A Sailor’s Guide to Earth, which debuted at the top of the country chart and at No. 3 on the Billboard 200.

Then, in December, came the biggest shock of all: A Sailor’s Guide to Earth was nominated for Album of the Year, alongside blockbusters by pop superstars Beyonce, Adele, Drake, and Justin Bieber.

Many media outlets gently chided Simpson for being the least famous nominee by far in one of the most prestigious categories. Surely, there will be millions of viewers on Sunday for whom Simpson is an unknown quantity. Even Simpson himself expressed regret that Frank Ocean — who withheld Blonde from consideration — wasn’t there in his place.

But that Simpson will be at the Grammys at all — just a few years removed from playing dive bars — is pretty incredible. How in the world did this happen?

I’d be lying if I said that I expected Simpson to become an industry-feted star after spending an hour with him back in 2014. I thought Simpson’s music was great, but that’s hardly a predicator of future success. In fact, I wasn’t even sure if Simpson would cut it as a cult artist. With Metamodern Sounds, he seemed perversely intent on defying the whims of the small following of country purists who loved High Top Mountain. In our interview, he went out of his way to alienate “real country” folk, claiming that Skrillex and Eliminator-era ZZ Top — that’s the one with synth-driven MTV hits like “Gimme All Your Lovin'” and “Sharp Dressed Man” — were bigger influences on his music than any country artist. He also insisted, counterintuitively, that the album’s apocalyptic climax, “It Ain’t All Flowers,” was his attempt to make a dubstep song using country instrumentation.

That night during his set at the bar down the street, Simpson played “You Can Have The Crown,” a sly swipe at pop-country that closes with the following lines: “So Lord if I could just get me a record deal / I might not have to worry about my next meal / but I’ll still be trying to figure out what the hell rhymes with Bronco.” The country die-hards in the audience spontaneously responded by chanting “Toby Keith sucks! Toby Keith sucks!” Simpson just stared down at his guitar, looking embarrassed. Simpson had egged them on by playing the song, but he didn’t want to be anyone’s backward-looking traditionalist.

Simpson is often classified as an outsider in the mold of the original ’70s outlaws: Willie Nelson, Waylon Jennings, Billy Joe Shaver, Tompall Glaser, and Kris Kristofferson. But no matter his criticism of institutions such as the Academy of Country Music, Simpson didn’t strike me as an anti-establishment ideologue when I spoke with him. My impression of Simpson was that, above all else, he’s a contrarian. Put him in Nashville and surround him with bro-country pretty boys, and he’ll write “You Can Wear the Crown.” Insist on comparing him to Waylon Jennings, and he’ll start raving about how the greatness of Skrillex. He just didn’t want to be pigeon-holed — not even as an edgy outsider who hates being pigeon-holed.

“I listened to everything growing up, man: blues and funk and jazz, all kinds of old ’60s rock,” Simpson told me. Looking back, I wonder if he was already pondering his next record, a philosophical treatise on fatherhood in which any lingering traces of country orthodoxy in Simpson’s music left standing after Metamodern Sounds are finally swept away. With A Sailor’s Guide to Earth, Simpson made a kaleidoscopic record informed by all of the music other than country that informed his upbringing.

In retrospect, Simpson’s laissez-faire “I’ve achieved all I set out to do” attitude might’ve been another contrary moment. Arguably the most important element driving Simpson’s improbable rise has been his proficiency as a live performer, aided in no small part by an excellent backing band highlighted by the dazzling guitarist Laur Joamets, who got his start as a house musician on the Estonian version of American Idol before hooking up with Simpson via producer Dave Cobb.

As good as his albums are, Simpson has likely won more converts due to a series of standout performances on television, culminating with a much-celebrated appearance last month on Saturday Night Live that proceeded to go viral. It’s impossible to watch him on SNL and argue that Simpson doesn’t care about being a star. As the stages have gotten bigger and the spotlight brighter, Simpson has routinely seized the opportunity to grow his audience.

At the Grammys, I suspect that Simpson will go over like Mumford and Sons did back in 2011. At the time, the retro-folk act was, like Simpson, largely unknown to the average music fan. But the group’s rendition of “The Cave” was — even if you can’t can’t stand Mumford and Sons — unquestionably stirring, and the group subsequently enjoyed a sizable spike in popularity. Based on the response to the SNL performance, I would bet on Simpson having the same kind of impact at this year’s Grammys.

Perhaps I was being hasty when I posited Simpson as a mere reactionary. To the contrary, Simpson has a resolute inner spirit that has guided him along an idiosyncratic career path, from the niche traditionalism of High Top Mountain to the iconoclastic (and surprisingly popular) bluesy psych-rock of A Sailor’s Guide to Earth. And that spirit derives in large part from Simpson getting started at a relatively advanced age. At 38, he’s the oldest nominee in the Album of the Year category, though he also has the youngest career. Bieber is a weathered music-industry veteran in comparison.

Simpson’s life experience has instilled a stubborn resolve to block out the outside world and be his own man, which has, paradoxically, made him a rising star. Simpson is both admired for sticking to his guns, and rewarded for it commercially — the most enviable position for an artist to be in.