Becky Fluke

This article originally appeared as the cover story in the December 2017 issue of Relix.

Chris Stapleton sill retains fond memories of performing “Midnight Train to Memphis,” the rousing, rowdy seventh track on his new album From A Room: Volume 2, during his initial trip to Bonnaroo.

The singer/guitarist, who is currently hailed as one of country’s biggest crossover sensations, received a spirited reaction from the crowd, many of whom had never seen him perform before. In fact, very few individuals outside the Nashville songwriting circles who held him in the highest esteem were all that familiar with Stapleton as he played with his group that Saturday afternoon at Bonnaroo.

That’s because Stapleton did not deliver a soulful reading of “Midnight Train” with his touring group on the main stage in 2016, but with his bluegrass band The SteelDrivers at The Other Tent in 2009.

The fact that Stapleton— whose From A Room: Volume 1, which hit No. 1 on the Billboard Country Albums charts this past May, as a follow-up to the similarly chart-topping Traveller—chose to cut a new version of “Midnight Train,” featuring a snarling electric guitar rather than a sprightly banjo lead, is a testament to the depth of his catalog, the nature of his friendships and his expansive view of the musical constellations.

The decision to name two albums after Nashville’s historic RCA Studio A—where Waylon Jennings, Willie Nelson and Dolly Parton all recorded—affirms his regard for tradition. However, he is not a dogged traditionalist. Instead, he’s willing to seek out inspiration from wherever he finds it, whether that’s through the sounds of Ray Charles and Otis Redding or exchanges with Tom Petty and Justin Timberlake.

His perception of Bonnaroo does not comport with that of an insular country artist. As he looks back on The SteelDrivers’ 2009 set in The Other Tent, he acknowledges: “Bonnaroo is one of those things that everybody wants to check off as a box. It’s one of those things that can elevate you as a performer. There are several festivals like that—Lollapalooza, Coachella and some of these big name places—where if you can just get your name on the bill, it becomes this thing where even the people that aren’t there can look at it and go, ‘Oh, they’re playing Bonnaroo!’ It kind of legitimizes you in certain ways. So it was a big deal for us to get to play that.”

Stapleton’s words do not sound like those of an archetypal country artist. Yet his vocals do, with their graceful yet gravelly timbre. On November 8, the Country Music Association affirmed this assessment by naming him Male Vocalist of the Year for the third consecutive time, while also selecting From A Room: Volume 1 as Album of the Year, the same honor given to Traveller in 2015.

To see him perform with his full touring act, which includes his wife Morgane Hayes as well as bassist J.T. Cure, who previously joined Stapleton in his garage band The Jompson Brothers— the project that followed The SteelDrivers—one can understand why he also has received multiple CMA nominations as Entertainer of the Year. However, Stapleton and company deliver such a robust, commanding live show that he remains free of any genre constraints.

For Stapleton, it all flows from the song. Since the composition itself is paramount—without consideration of radio format or other classifications—his work has been recorded by a diverse collection of artists from Adele to Kenny Chesney to Joss Stone to George Strait. His songwriting efforts have also informed his personal pursuits, guiding him to various projects over the years. The story of how this all came about reflects equal parts steadfastness and serendipity.

Stapleton grew up in rural Kentucky, where his initial exposure to music came through the radio in his father’s car. There, he absorbed the work of outlaw country artists such as Waylon Jennings, Willie Nelson and Merle Haggard, as well as Otis Redding and classic R&B. “There are some people who might feel that all of those don’t quite fit together,” he says, “but I connected with all of them. It just felt right to me.”

Stapleton took up the guitar and began writing songs in his teens but he had no expectations of pursuing a career in music. If anything, he hoped to be a professional football player. He was a high-school running back of some renown. A local newspaper clipping during summer practice of his senior year touts his prowess and notes that he is getting “looks from Princeton and Army.” While Stapleton made recruiting trips to both schools, the high-school valedictorian ultimately decided to enter Vanderbilt to pursue an engineering degree. Still, he acknowledges that he held out hope of making the Vanderbilt team.

“I’d gone to a camp there and really liked the coaching staff, so I wanted to walk on,” he says. “But when you’re 18, you think you’re better at things than you actually are. On my best day, I was six-foot, 210 and ran a 4.8 second 40-yard dash. To play Division I SEC, you’ve got guys that are defensive ends who are 6’7” and running 4.6s that weigh 270. I wasn’t that kind of material. I could’ve maybe played D2 or D3 and been average. If I had the skill and the ability, I would have probably played football instead of music. I loved football that much. I just didn’t have that ability.”

As it turned out, he also didn’t have the affinity to be an engineer. Although it was his father’s profession and various family members held math-based degrees, he looks back and explains: “I just picked something. In retrospect, it wasn’t really me.” So Stapleton never completed his program at Vanderbilt, and this is where his story takes a fortuitous turn.

“I finished the semester I was in—I didn’t stop in the middle of something. But I decided to chill out for a minute and work some different jobs—I sold cars, drove an ice truck, worked at pizza joints—just whatever to pay the bills. I moved into a nearly commune-type place in Morehead, Ky. It was a house, but it was very dilapidated and got condemned not long after I moved out. My bills were $80 a month, so I could play music and get better at it, while working other jobs to figure out what it was I wanted to do.

“Nobody I knew was a professional musician or songwriter. It was not something that ever crossed my mind, until I ran into a guy named Steve Leslie through a mutual friend. He was a salaried songwriter, which I didn’t know existed. As fortune would have it—now that I’m in the music business, I know how rare this is—he said to my friend, ‘If you know anybody that writes songs, I’d love to help them out.’ So my friend gave me his number and, being green and unknowing of what the process was, I called him up and said, ‘Hey, I write songs.’”

Leslie invited Stapleton to send him some material and, a few weeks later, after assessing five songs, suggested they attempt to write together.

Many years later, Stapleton looks back with some astonishment at what ensued. “I went back and forth for a couple of months and met some people and then I moved to Nashville. Four days later, I had a publishing deal. And I’ve been working as a professional songwriter, musician’s demo singer— whatever you want to call it— ever since. That’s my story. It’s the luckiest story in the world when you say it out loud. But that really is my story.”

Stapleton arrived in 2001 and, through a steady work ethic, soon found success as a professional songwriter at Sea Gayle Music Publishing, a company founded two years earlier by Music Row veterans Brad Paisley, Chris DuBois and Frank Rogers. Prior to the release of Traveller in 2015, Stapleton amassed a catalog of over 1,000 songs and his work yielded more than 170 album cuts, including chart-toppers for Kenny Chesney (“Never Wanted Nothing More”), Darius Rucker (“Come Back Song”), George Strait (“Love’s Gonna Make It Alright”) and Luke Bryan (“Drink a Beer”).

It was also during this time that Adele covered “If It Hadn’t Been for Love,” which appeared on The SteelDrivers’ 2008 self-titled debut. That record, and the band itself, was another direct product of Stapleton’s songwriting. One of his earliest collaborators was Mike Henderson. In 2003, their “Drinkin’ Dark Whiskey” became the lead track on Gary Allan’s platinum-selling See If I Care album, and they later recorded their own version with The SteelDrivers.

“I had written a bunch of songs with Mike, who is a wonderful poet and songwriter, and brilliant musician,” Stapleton recalls. “We had a weekly standing appointment, and we both had an affinity for bluegrass. After we’d written a bunch of songs together, Mike said, ‘Hey man, do you want to play some bluegrass, just for fun?’ At this point, I’d only been songwriting for three or four years but I had settled into being a songwriter. That was my space in the world. So when Mike brought up playing again, I thought it sounded like fun. We were going to get together once a week, find a VFW gig and play Flatt & Scruggs songs—old standards and things like that. He called the rest of the guys—Richard Bailey, Mike Fleming, Tammy Rogers—and we got together at his house and started jamming. Then we started pulling out songs that we’d written and, slowly but surely, we had a catalog of things to play other than covering Flatt & Scruggs.”

The ensemble recorded two albums before Stapleton departed in 2010; he was touring with them when Morgane became pregnant with their first son. She was a fellow country songwriter and performer he met in 2003. For a time, they worked for neighboring publishing companies. (Her credits include Carrie Underwood’s “Don’t Forget to Remember Me,” which peaked at No. 2 on the Billboard Hot Country Songs chart.) “While she was pregnant, she was also singing background vocals with Lee Ann Womack,” Stapleton now explains. “It became a very difficult dynamic, where I’d be gone and she’d be home—or she would be on the road and I’d be home. It’s like when somebody works a night shift and their spouse works a day shift.”

So he returned to his own day shift at Sea Gayle. However, Stapleton soon found another outlet for his live performance expression a bit closer to home—he started playing in his garage. There, he ditched his acoustic guitar, plugged in and began exploring ‘70s rock with a new quartet, The Jompson Brothers. “It just came from hanging out with friends, writing rock songs and jamming out on riffs,” he says. “We’d have stacks of beers left out in the garage—we were literally a garage band. Eventually, we decided we’d try and start playing out in the clubs because it felt like a natural thing to do. We enjoyed ourselves, but we were so independent that nobody knew who we were.”

That soon changed—The Jompson Brothers played a limited number of live dates, as its members’ schedules permitted, sharing bills with such acts as North Mississippi Allstars, J. Roddy Walston and the Business and The Dirty Guv’nahs. In 2010, No Depression co-founder Grant Alden wrote a piece on the group that echoed Jon Landau’s 1974 anointing of Bruce Springsteen (albeit with Alden’s tongue somewhat in cheek), which began: “I have seen the future of rock ‘n’ roll…” Others wrote pieces that referenced Gov’t Mule and Drive-By Truckers.

The Mule comparison carried some significance to Stapleton, who affirms: “I respect Warren [Haynes] so much as a player, writer and touring musician. There are few guys that are as respected as he is among musicians.” In October 2015, as a solo artist, Stapleton would later open a few dates on Haynes’ Ashes & Dust tour. “One night, Warren got me up to play ‘Desperados Waiting for a Train,’ the Guy Clark song,” he recounts. “That was one of the coolest moments for me because, several years before—one of the first times I ever played in an amphitheater—I played acoustic solo before Lynyrd Skynyrd and the Allman Brothers.”

As for The Jompson Brothers, in 2010, the group released a self-titled album, full of brawny, exuberant tracks. American Songwriter likened them to Led Zeppelin and also cited their “riff-driven, fist-pumping sonic assault.” The album included “Secret Weapon,” a song that Jason Aldean began using as his walk-out music, disclosing, in a Radio.com interview, “It’s just one of those songs that gets you fired up ready to go.”

The Jompsons—whose efforts began to wane in early 2013—never approached country success, nor was that their intention. Instead, they were a natural compound of Stapleton’s friendships, songwriting proclivity and a new element: his comfort with the electric guitar.

Stapleton, who is now the lone guitar player when he tours with his own group, made his live electric debut at, of all places, the Grand Ole Opry. About four years into his stint as a Nashville songwriter, Trent Willmon asked Stapleton to join him on background vocals for a gig at the Opry. Stapleton assented and, after Willmon learned that Stapleton had an electric guitar at home, he encouraged him to bring that as well.

“I wasn’t really thinking about what I was committing to. I was thinking he was going to have me strumming some chords. But it turned out that I had to learn some bars and things,” Stapleton says with a laugh. “I’d never played electric guitar on a stage before in my life, and wound up doing it on the Grand Ole Opry. So I started fooling around with the electric guitar and then the rock thing came up, and I bought a Jazzmaster at Corner Music in Nashville—not because I was looking for it, but because I just picked it up and liked it. I’d never thought about that guitar before—everybody had a Strat or a Tele or something like that. Then I had a 410 Bass [amp] that I used because that’s what Mike Henderson used. I began hunting things, and I eventually got down to the rig that I use now, which is essentially Jazzmasters and early ‘60s Princetons.”

For someone who “had never even really played a solo on guitar,” Stapleton was a quick study. Years later, when it came to his solo band, the role ultimately fell to him. Just prior to the release of Traveller, he formed a group that included Cure and drummer Derek Mixon, along with pedal-steel player Steve Hinson and Jimmy Wallace on keys. However, a few weeks into their tour, both Hinson and Wallace bowed out. (“Travel was pretty rough in those days,” Stapleton acknowledges.)

With a few gigs looming over the coming weekend, the trio came together on a Wednesday to see if they could make it work. They slogged it out that night and determined that Stapleton could carry the load on guitar. “It was uncomfortable for a minute— and still is sometimes—but I’ve at least sort of settled into what I’m capable of doing on the guitar, trying to find a way that’s musical and serves the song.”

Stapleton is characteristically modest about this, but it’s worth noting that he did find himself trading licks alongside Bonnie Raitt and Gary Clark Jr. at the 2016 Grammys during a B.B. King tribute. (On the same night, he also took home awards for Best Country Album for Traveller and Best Country Solo Performance for the title track.)

Stapleton names B.B. as one of his influences, citing the triumvirate of Kings: Freddie, B.B. and Albert. Beyond these blues icons, he points to Mike Henderson (“I try to steal as much of his stuff as I can”) as well as former NRBQ guitarist Al Anderson (“Another good songwriting friend of mine, but also a great guitar player”). Then he names an oft-overlooked guitarist, whose work also holds deep meaning for him: Mike Campbell of Tom Petty’s Heartbreakers.

Petty and his bandmates are entwined within Stapleton’s musical DNA, as Petty’s Wildflowers is “probably my favorite record of all time.” There was a moment in 2013, when Stapleton made a direct appeal to his hero. After Petty issued a remark that was slightly dismissive of contemporary country music, Stapleton posted “An Open Letter to Tom Petty.” He wrote:

Dear Tom Petty,

Sincerely, Chris Stapleton

This past summer, Stapleton realized one of his few remaining career goals, when he opened three dates for Petty (a show at Wrigley Field in Chicago, followed by a pair at Milwaukee’s Summerfest). Although the two musicians talked shop, Stapleton’s missive from four years earlier never entered the conversation.

“I’m sure he didn’t remember it or think anything about it at the time. The gist of it—some people may have taken it as me being defensive, but it wasn’t that at all—it was, ‘Hey, man, if you really like country music so much and you care about it, come participate and let’s make it better.’ I never got a response and I didn’t expect one, but I felt it was worth saying. And also, I selfishly hoped that maybe Tom Petty would read it and go, ‘Hey, man, let’s do something.’ Because why not? If you don’t ask, the answer is always no.”

Stapleton pauses and his voice catches, as he reflects on Petty’s untimely passing in October. “When my booking agent first told me that they were thinking about having me out on the road, I didn’t figure it was real. And in the world of things that I get to do—which seems increasingly surreal every day—that was right at the top of the list. It was very cool. The last thing he ever said to me was: ‘I hope we get to do more of this.’ And I left there thinking that we might. Like so many in the musical world and, of course, the guys in his band, I was so heartbroken to learn that he had passed. I cried about it. That was a hard day for me.”

Stapleton’s emergence as a critically lauded performer and platinum-selling artist in his own right came about felicitously over lunch with a pal. Brian Wright had started his career in A&R at Universal at the same time that Stapleton had arrived in Nashville, receiving a promotion to vice president a few years later. “I thought we were just going to talk about the state of the world and catch up on life,” Stapleton recalls. “When we got to the end of lunch, he looked over at me and said, ‘Hey, why don’t you come over and make a country record at Universal?’ I didn’t really have a response. I said, ‘Well… OK, let me think about that.’ At the time, I had no thoughts of doing anything other than continuing to play rock-and-roll and having a good time. So I told him: ‘Let me go home and talk to my wife about it.’ When I spoke with her about it, she said, ‘Well, as long as you get to do what you want to do, I don’t see why you wouldn’t do it.’”

But the album he ended up making was never released. Shortly after completing it, Stapleton played the record for Luke Lewis, the head of Universal Nashville, who, in a story that is not altogether uncommon in the realm of major label life, stated that he would be leaving Universal the following week. “Normally, for a guy in my position—I was 35 or 36 at the time—that spells the end,” Stapleton reflects. “Then Mike Dungan came in and listened and said, ‘Well, I don’t really hear what I’m wanting to hear out of this. Let me sit on it for a minute.’” Although Dungan wasn’t enamored with the recording, he remained committed to the artist signed by his predecessor, rather than dropping Stapleton from the roster.

While initially frustrated, Stapleton eventually opted to push forward and make Traveller with producer Dave Cobb at Nashville’s RCA Studio A. Stapleton turned to Cobb after hearing his work on Sturgill Simpson’s Metamodern Sounds in Country Music. “There was a sound on there I had been chasing, but hadn’t been able to achieve. I thought it was something long gone, that modern engineers didn’t do it that way. But Dave somehow had the juju. He was a student of the history of engineering. If you name a Rolling Stones record, he could tell you the name of the microphone and preamp and all those other things that are on there—he’s an encyclopedia of that stuff.”

Stapleton and his core band (including a few guests such as Willie Nelson’s harmonica player Mickey Raphael who would go on to gig with Stapleton) took a loose approach in the studio. Most of the record was tracked live without charts or overdubs of any sort. The result was by no means a traditional country record—it had something of a rough-hewn edge—but it was a pure expression of Stapleton’s 15-year run in Nashville. After Stapleton’s tenure in the community and all the work he had done for other artists over the years, he had plenty of folks rooting for him. Traveller soon earned plaudits for its authenticity and song craft, but it still remained to be seen how the public at large would respond.

Then on Nov. 4, 2015 Stapleton’s career finally hit overdrive, thanks to Justin Timberlake and a sequence at the CMAs that Stapleton describes as “8 minutes that can change your life.” There, he took the stage with Timberlake on acoustic guitar for a performance that began with Traveller’s “Tennessee Whiskey,” followed by Timberlake’s own “Drink You Away.” Moments into the national broadcast, Chris Stapleton became an overnight sensation, 15 years in the making.

Stapleton had no inkling that the performance would yield this type of reaction; he just knew that “we were going to have fun out there.” The two had become unexpected pals through another instance of happenstance a couple of years earlier. A mutual friend had pointed Timberlake to a Stapleton video on YouTube, which eventually led Timberlake’s wife, actress Jessica Biel, to call and ask, “Hey, I’m always looking for things that Justin hasn’t done yet. Would you come play his birthday party?’”

Stapleton pauses to chuckle as he reflects on the moment: “So I wound up being part of his birthday festivities one year. I thought it was going to be a large gathering, but it wound up just being six or eight people, casually hanging out. We became friends from there and have been friends ever since. So when I called him up to ask if he’d like to come do this, he was like, ‘Yeah man, I’m there.’ It was as simple as that.”

The public response was simply overwhelming. Stapleton and his group took the road for an extended tour that transformed him into an arena-level star. Although he had only one album to his name, Stapleton was buoyed by his years as a songwriting craftsman, giving the newly energized live performer a wealth of material to present.

Eventually, he decided to wind down his touring cycle to record a proper follow-up to Traveller. As it turned out, he delivered two. He reentered RCA Studio A with producer Dave Cobb to explore his deep well of material. “We had some time blocked off to record, but we’d been running really hard,” he says. “Touring and songwriting—some people can do both in tandem, but I don’t think I’m one of those guys. I need to really be still to write songs. I also had a fairly large back catalog of songs that I love very much. If they didn’t get recorded, it wasn’t because we didn’t like them; it was just because we didn’t get to them.”

Some of the curation he left to Morgane. As he explained on Charlie Rose: “Her taste in songs is sometimes a puzzling thing to me. But I trust her, without fail, on things that she likes because she has excellent taste in just about everything but men.”

While she had long been his sounding board and creative partner, with the release of Traveller, she also joined his band on the road. It was something they had contemplated, going all the way back to his SteelDrivers days. “A goal of ours was always to get to a place where we could be touring together and have the family out. Right now, we have my father-in-law, my mother-in-law, my sister-in-law and both of my children. [In an October 30 Instagram post, Morgane also announced she was pregnant with twins.] My mother comes out when she feels like it. We have a family bus, and the kids are homeschooled, so we very much get to be a family on the road. Beyond all the other professional dreams, that’s a dream come true to get to do that.”

As for the challenges of taking the stage with one’s life partner, an endeavor that the two share with Derek Trucks and Susan Tedeschi, he notes, “We’re a pretty good team and get along fairly well and understand—much like I’m sure Derek and Susan do—that we have a job to do when we go out there. Obviously, anyone can have a bad day, and you bring that energy to the show or to a room when you walk in. Those times are unavoidable, and that’s just life. But I will say this: Anybody who’s been in a band for any amount of time will say that just being in a band is being married to a group of people. It has to be intimate for it to work. Everybody knows everybody’s personal stuff, and we’re all pulling for each other. So the fact that my wife and I are married is not very different. It’s great for us on a personal level, but the band part of it is just like being in a band.”

When Stapleton returned to the studio, he brought his band with him once again, in an effort to capture the energy and connection of his live performances in “a historic room where you get to feel the ghosts in the walls, informing and elevating what do you.”

Stapleton views both volumes of From A Room as a collective body of work, selected and performed with a similar intent. “I recorded some of these songs because of the people I wrote them with. A lot of songwriters on these records weren’t on the Traveller record. I felt it was important to show that part of my songwriting, particularly with Mike Henderson,” he says.

That’s certainly true of “Midnight Train to Memphis,” his collaboration with Henderson that first saw the light of day with The SteelDrivers.

“That’s a song I’ve always played,” Stapleton explains. “The way it is now is more in line with the spirit of how it was written. We adapted it to the banjo and it made its way into The SteelDrivers’ catalog because it was kind of a prison song, which matched the demeanor of what the band was. But it was a rock song adapted to bluegrass, and now we play it with loud electric guitars and a blues backbeat. I carried that song with me to The Jompson Brothers, and with my solo stuff. It’s a song I’ve always played live, but we’re doing it this way now, so we thought to document it.

“I always looked at songwriting, touring and playing live music as one whole thing, not separate entities; one always feeds off the other. These songs very well could’ve been recorded on Traveller, or any other project I’ve done previously—they’re songs that I love and my wife loves, and they’re always part of the equation. I read a Billy Gibbons interview one time, and he said he tried to record things he would want to listen to. That’s something I keep in my heart when I’m trying to record music. That’s very much the attitude of these records.”