How Chris Stapleton Started Over and Made His Most Personal Album Yet

As Chris Stapleton pondered album titles in March, he kept coming back to the idea in the opening track, “Starting Over.” There was something about a fresh start that struck the 42-year-old five-time Grammy winner.

“There’s hope in having to start over,” Stapleton says. “Within that idea, there’s the promise of making something a little better.”

Starting Over comes three years after his two-volume set, From a Room, and it’s his most personal work yet. He doesn’t consider himself the type of “guy who listens to his stuff all the time,” but he finds comfort in how these new songs let him “relive very specific moments of my life. There were certainly things that were written in a therapeutic sense.”

As with each album, the singer-songwriter-guitarist dips his toes into a little bit of everything, from haunting soul on “Cold” to the dirt-road rock ’n’ roll on “Arkansas”—on which he sings, “Well, we burned through the one-light towns like a scalded dog.”

The latter song is what you might expect when you hear the tag “outlaw country.” Stapleton doesn’t consider himself part of that brand, though, remembering what musician Marty Stuart once told him: “A real outlaw doesn’t need a sign that says he’s one.”

“I’m a guy who plays music who happens to have long hair,” Stapleton says. “Am I country? Shoot, I’m from east Kentucky, and I don’t think it gets any countrier than that. If you wanna call me that, sure, I’ll take it and wear it proudly, but there are a lot of other influences that I would be quick to mention.”

Among those influences are the country legends known by one name—Waylon, Willie, Merle—as well as Ray Charles and Otis Redding. Growing up in Staffordsville, Kentucky, in the ’80s and ’90s, Stapleton was drawn to those sounds as much as he was to then-contemporary chart-toppers like Tom Petty and the Heartbreakers, Sheryl Crow, and Luther Vandross. Hell, his first concert was Bon Jovi.

None of the artists he rattles off have anything to do with one another, other than how they came into his consciousness “somewhat by accident or by walking into a Walmart,” Stapleton says, laughing. “It’s a feather in the cap of my parents. I don’t remember them saying to me, ‘Well, you can’t listen to that kind of music or this kind of music.’ It was all on the table.” The mix of sounds shows in his music nearly three decades later, says collaborator and Tom Petty and the Heartbreakers guitarist Mike Campbell.

“A lot of musicians get into the business for the wrong reasons or want to just make a lot of money,” Campbell says. “Chris strikes me as someone who would make music whether he’d make money or not. He just loves music.”

When you listen to Starting Over, the love and respect for music is obvious. “Whiskey Sunrise” gives a nod to the Animals’ “House of the Rising Sun.” The opening title track feels as gentle and contemplative as the title track on Stapleton’s favorite album of all time, Petty’s Wildflowers. While recording Stapleton, producer Dave Cobb says he feels the history of all those influences come alive.

If the music displays those influential facets, the lyrics are as unflinchingly honest. On the ballad “When I’m With You,” Stapleton calls out his own privileged status as the modern country star while admitting he’s constantly searching for the next great song. “Maggie’s Song” is a tune for his 14-year-old dog that passed away that he says he wrote in 10 minutes.

That honesty goes past the lyric page and performances. Ask him about his wife, Morgane, and he’ll joke that she has great taste in everything except men, that “she’s a lighthouse when I’m in the dark.” As sweet as he sounds when talking about his wife, he doesn’t mind reflecting on tough emotional times. He’ll tell you that Starting Over isn’t all joyful stuff.

Consider “Watch You Burn,” the track where Stapleton delivers a sermon on gun violence based on the 2017 shooting at the Route 91 Harvest festival in Las Vegas that killed 58 people and wounded 850 more. “Only a coward would pick up a gun / And shoot up a crowd trying to have fun,” he sings at the top of the song, promising retaliation: “You son of a bitch / You’re gonna get your turn. … Devil gonna watch you burn.”

He’s no politician, and he doesn’t have all the answers. However, when asked about topics like gun violence, lack of care for U.S. veterans, or supporting the Black Lives Matter movement, Stapleton won’t back down from his beliefs.

“I’m for love, kindness, equality, being good to good people,” he says. “Some things don’t register to me if it’s against humanity.”

Like Sturgill Simpson and Jason Isbell, Cobb says, Stapleton is comfortable in his own skin—what you see is what you get. Before recording with Stapleton, Cobb was a fan of the bearded singer’s former band, the SteelDrivers. When Cobb got a call to work on what would eventually become Stapleton’s quadruple-platinum debut, 2015’s Traveller, the duo hit it off, sharing similar musical influences and work ethics. Cobb has worked on every Stapleton album since, and the atmosphere is laid back.

“[Stapleton is] not trying to chase any trends,” Cobb says. “We don’t go in and say, ‘This will be our disco record.’ [Simpson, Isbell, and Stapleton] don’t say, ‘Let’s go make the countriest album to show everybody we’re outlaws.’ That’s who these people are.”

While recording Traveller, Cobb noticed how Stapleton always seemed to know the perfect time to cut a song. The singer and his band would arrive at noon at RCA Studio A in Nashville. They’d eat lunch, goof off, order dinner, have a few drinks, and maybe start recording around 8 p.m. Everything was cut live.

The process worked as Traveller took two weeks to record and mix. Starting Over, on the other hand, took nearly two years. The initial plan was to record at the end of 2018 with a release date scheduled for sometime in 2019. This time around, instead of returning to RCA Studio A, Stapleton, Cobb, and the band set up sessions at Hillbilly Central, a storied room in South Nashville that is now home to Compass Records, and at Muscle Shoals Sound in Alabama.

“I was feeling a little adventurous,” Stapleton says, adding that sessions in Muscle Shoals were plagued because the town lost power. “I’m a big signs-from-the-universe guy. [The power] would work for a minute, then it was gone. I said, ‘Maybe it’s not the time. Let’s just put it down.’”

Frustrated with the lack of material, Stapleton went back on the road for a few gigs in early 2019, then took time to recharge his batteries. Cobb says the break was necessary because the singer wanted to make sure the songs felt right. During that reset, Stapleton flew to Los Angeles in July 2019 to write with Campbell.

Campbell and Stapleton first met in 2017 when Stapleton opened for Tom Petty and the Heartbreakers at Wrigley Field in Chicago. Stapleton’s band had to pass through the headliners’ dressing room to get to the stage, and the singer made a point to introduce himself to his heroes.

“[Campbell] is my all-time favorite guitar player,” Stapleton says. “Not that I play or sound anything like him, but I’ve done plenty of trying. You can try to be Michael Jordan all day long, but you’re not.”

Collaborating with Stapleton was an odd proposition for Campbell, who usually writes alone in his backyard cabana-style rehearsal room next door to his recording studio. However, the three-day trip yielded around five songs and more sketches. Stapleton’s idea for a song called “Fuck That Guy” became the first single on Reckless Abandon, the upcoming album by Campbell’s band, the Dirty Knobs.

Though Campbell was out of his comfort zone, they bonded over musical influences and worked out a few song structures while sipping Tennessee honey whiskey.

“[Stapleton] reminds me of Tom [Petty],” Campbell says. “[Stapleton’s] not obnoxiously loud. He’s very astute and focused on music.”

Campbell provided guitar licks to songs like “Arkansas” and “Watch You Burn” on Starting Over, and the Heartbreakers’ Benmont Tench also assisted, contributing signature keys and B3 Hammond organ to several songs, including “Cold,” a ballad captured at Muscle Shoals Sound.

When Stapleton restarted sessions for what would become Starting Over in late 2019, “Cold” felt more finished than he originally thought. The main ingredients—guitars, bass, vocals, drums—were all complete. All the song needed was strings and Tench’s keys. The strange trip was worthwhile in the end, and Stapleton thinks he caught some ghosts and supernatural moments from the studio.

“There’s a reason I go to these rooms: If you’re lucky to get a little bit of that magic dust off those walls, it informs things,” Stapleton says. “It was probably my fault for sending us on a journey outside of our usual processes, but we wound up with some things we wouldn’t have had, and I think the record is better for it.”

Other tracks like “Whiskey Sunrise” and a cover of Guy Clark’s “Old Friends,” both recorded at Hillbilly Central, also made the final cut. As the band worked a few earlier ideas out, more songs were recorded at RCA Studio A, next door to the historic room where Dolly Parton recorded “I Will Always Love You.” Stapleton, Cobb, and the band fell right back into the groove.

Cobb compared Stapleton to a Jedi during those 2019 sessions. By then, the singer was in a great headspace and finally found the right atmosphere to continue working on the album.

“Chris brought his A game,” Cobb says. “I love all the records we’ve done, but this is my favorite record he’s done to date.”

Starting Over was completed by January. Like countless musicians this year, Stapleton had booked a supporting tour. Among those dates was a return to Wrigley Field, with Campbell’s band opening this time around. But the world had different plans. As Stapleton’s band played its first and only show of the year on March 11 in Corpus Christi, the NBA made the decision to shut down the season.

“I walked off stage, and shit got real,” Stapleton says.

The band packed up and headed back to Nashville. The tour was canceled, and subsequent dates were rescheduled to 2021. The singer isn’t a stranger to staring down and overcoming challenges—that’s the connective tissue of his entire career.

In 2013, his first major-label single, “What Are You Listening To?” was DOA. A week after the single barely made a divot on country charts, Stapleton’s father died in October 2013. Already an established songwriter, Stapleton needed a break. Along with his wife and photographer Becky Fluke, he flew to Arizona, picked up a 1979 Jeep Cherokee, and drove it across the country. On that trip, Stapleton wrote the song “Traveller.”

When he returned to Nashville, Stapleton sat down with UMG Nashville president Cindy Mabe, outlining a plan to cut an entire album and then tour. Stapleton wasn’t concerned with singles. He just wanted to play, because that’s all he had ever known. Thirty-seven when Traveller was released, he thought it might be the only record he’d produce.

“I told myself that if I got to 40 years old and nothing was happening, I was going to give up on the touring thing and just settle into songwriting,” Stapleton says. “But that series of events, the graciousness of someone allowing me the freedom to do something unconventional by modern label standards—those things really helped make what we get to be now.”

Stapleton is speaking from a makeshift TV studio he built because he lives so far out in the Tennessee country that “nothing works,” he says, laughing. Hopefully, he and the band can tape performances and interviews to send to talk shows. Like everyone in this moment, near the end of 2020, he’s starting over. He’s as excited as he is unsure of what the future holds.

“The uncertainty can be a catalyst for all kinds of new avenues, for things we are capable of, or maybe we should have been doing all along,” he says. “It’s not necessarily easy. It’s probably not even meant to be. But that’s the human experience—you get faced with a problem, and you figure out what it is you can do that turns that into an opportunity for a solution.”

Matthew Sigur is a writer, musician, and comedian based in Chicago.