From Waffle House to the Opera House, Sturgill Simpson is a star

Some earmarks of commercial and critical success are more obvious than others.

Take, for instance, when Sturgill Simpson’s new A Sailor’s Guide to Earth album simultaneously debuted to No. 3 on the all-genre Billboard 200 chart in April as well as the trade magazine’s country charts at No. 1. That and two sold-out shows this week at the Lexington Opera House would seem to indicate just how widely accepted the Breathitt County native’s roots-informed, stylistically far-reaching brand of country music has become.

But let’s face it. You’re not really a show business celebrity unless you are afforded a major opportunity to poke fun at either yourself or some element of the artistic surroundings that created a buzz about you in the first place. That arrived last month with Simpson’s appearance on The Late Show with Stephen Colbert.

Sure, the engagement offered a proper forum to showcase the just released A Sailor’s Guide with a blues-heavy performance of Brace for Impact (Live a Little), which strayed from the traditional country of Simpson’s early music to an Americana amalgamation that blended slide guitar, churchy organ runs and horn fortified grooves. That was ample evidence of how far Simpson had come since his days of playing Lexington haunts like The Dame a decade earlier with the roots-country outfit Sunday Valley.

But Colbert had a double agenda for having Simpson as a guest. The comedian was determined to get a song of his own on the jukebox at Waffle Houses around the country. So he and his writers came up with No Shirt, No Shoes, No Knuckleheads, a yarn about the proper late night etiquette for dining at the popular string of diner-style eateries. Simpson became a willing accomplice by singing the tune with Colbert.

“No spitting, no yelling, no slip-and-slides,” went a verse that Simpson sang with pokerfaced solemnity. “If you’re going to get sick, you better step outside.”

The irony, of course, is that Simpson’s booming career is no joke. As one of two Kentucky natives (Chris Stapleton being the other) helping change the stylistic face of country not by veering into video-friendly pop but by paying serious attention to roots, rock and R&B traditions, Simpson has tapped into a substantial fanbase — one hearty enough to underscore his critical reputation with commercial appeal.

Back in 2005, when Sunday Valley was opening local shows for the likes of Split Lip Rayfield and the Legendary Shack Shakers while promoting an indie debut album of its own, winning over any audience, country or otherwise, proved a challenge.

“We’ve actually gotten some people dancing at some shows,” Simpson said prior to a March 2005 opening set at The Dame for the Rev. Peyton’s Big Damn Band. “I can’t imagine how that happened.”

In the decade that followed, Simpson exited music and went to work for Union Pacific Railroad in Utah but briefly returned to Kentucky and Sunday Valley before settling on the artistic inevitability that Nashville would have to be his home if a music career was to be seriously pursued.

“My wife basically told me, ‘You’re going to wake up one day and be 40 years old and know that you never really had the chance to properly give this a go,’” Simpson said prior to a 2013 performance at Cosmic Charlie’s that coincided with the release of his debut solo album, High Top Mountain.

That recording was an ultra-traditional country project that utilized some of Nashville’s most seasoned session players (pianist Hargus “Pig” Robbins and steel guitarist Robby Turner, among others) and was produced by a then-unknown Americana stylist named Dave Cobb, who has since become the producer of the moment for his work with Stapleton, Jason Isbell and many others. While the music sounded traditional, the deep tenor of Simpson’s singing sounded like it soared straight out of the famed outlaw country movement from the mid 1970s.

A Cobb-produced followup, Metamodern Sounds in Country Music, surfaced in 2014. While it retained much of its predecessor’s traditional slant, it was an altogether trippier affair, both thematically (as charted in Turtles All the Way Down) and musically in the dashes of psychedelia peppered throughout the album.

The venues Simpson played began to grow larger, his commercial and critical appeal intensified and the sense that Kentucky had created one of its most daring country exports since Dwight Yoakam became wildly apparent. The latter trait really came into view when A Sailor’s Guide was released on the heels of Stapleton’s commercial breakthrough.

While the new album is Simpson’s debut for a major label (Atlantic) as well as his first record without Cobb (A Sailor’s Guide was self-produced), the music’s almost elastic ties to country were stretched even further to include elements of Muscle Shoals-style soul. “Everything is not what it seems,” he sings on one of the album’s bravest tunes, Breakers Roar, amid a waterfall of pedal steel guitar and strings while Keep It Between the Lines summons the spirit of Waylon Jennings even as its music flirts with vintage R&B and funk. No wonder the New York Times pegged Simpson as “a genuine alternative to alt-country” upon the album’s release.

But Breakers Roll turns out to be a rather prophetic tune, as it reflects an artist who relishes in dodging expectations, whether it’s a seeming devotion to the outlaw country academy or his current fascination with roots driven rock and soul. Everything — at least, musically — really isn’t what you thought it was. And you can take that to the Waffle House.

“Elvis was a way bigger influence than Waylon Jennings,” Simpson told the Times’ Jon Caramanica in March. “But you don’t wanna tell people, ‘I never really listened to Waylon.’”

This story was originally published May 15, 2016 at 7:47 AM with the headline "From Waffle House to the Opera House, Sturgill Simpson is a star."