Charley Crockett Is Taking Texas to the World

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efore Charley Crockett kicked off this particular show, he hung out, sipping from a red plastic cup and making small talk the same way he has before most concerts in his nearly two-decade career. He only got wide-eyed once, when someone in his camp asked how a rodeo could get so big, and relished the chance to explain its worldwide appeal. Brazilians dominate the American bull-riding circuit, Crockett said, because of the country’s long history of cowboy culture. Only when an event organizer shouted, “Charley, we’re ready!” did he snap back to the moment and calmly slide behind the wheel of a jet-black 1965 Thunderbird convertible.

This played out in a tunnel inside NRG Stadium, in mid-March at the Houston Livestock Show and Rodeo, just before Crockett headlined the massive event for the first time. As he put the car in gear, Taylor Day Grace — Crockett’s wife and a fellow musician — ran to the driver’s side of the T-Bird, kissed him, and said, “Have fun out there.”

Then, the coolest man in Texas drove himself up to the biggest stage in Texas.

“I’m not a cowboy, I’m a cowboy singer,” Crockett says. “That’s what Jack Clement said about Waylon, too. That’s in your mind. That’s that lifetime drifter mentality, man.”

He’s been a Texan since Day One, and to him, Selena Quintanilla Pérez’s 1995 appearance at the same rodeo — when she rode to the stage in a horse-drawn carriage — is the gold standard for any concert, Lone Star State or otherwise. Driving out in the T-Bird may fit Crockett’s style, but it’s also his way of paying tribute.

“Selena, to this day, is still the biggest-selling Tejano artist of all-time,” he tells Rolling Stone. “Before she did it, they said two things: Number one, a lot of the Mexican musicians refused to acknowledge a Tejana girl whose first language was English. They said it couldn’t be done, and she did it. The second thing was that she was a woman doing it. Tejano is what they call the genre, but the biggest Tejano artist is actually a Tejana woman. And she blew it up. Thirty years later, no one has been able to take it further. And that footage of her at the Houston rodeo, it affects me.”

Two days prior, Crockett lounged in a chair on the second floor of Austin’s Continental Club, the venerable dive on South Congress where he landed one of his first gigs in the Texas capital — a summer residency circa 2016. This time around, he had an interview with Rolling Stone, in between record-store performances for the release of Lonesome Drifter, his 14th studio album since 2015, and third in less than a year, following 2024’s $10 Cowboy and Visions of Dallas. The 11-track record dropped on March 14, making his Houston rodeo appearance three days later the de facto release party for an album that stands to join 2020’s Welcome to Hard Times and 2022’s The Man From Waco as Crockett’s signature records.

Lonesome Drifter showcases the qualities that landed Crockett on major stages like the Houston rodeo, Stagecoach festival, and Red Rocks Amphitheatre. The music ranges from hard country (“Life of a Country Singer,” “Under Neon Lights”) to twangy blues (“Easy Money,” “This Crazy Life”) to straight-up psychedelic rock (“Never No More”), all held together by Crockett’s autobiographical songwriting.

Crockett has woven so much of his life into his music that his story feels well-told. But to summarize, he was born in San Benito, Texas — not far from Brownsville and the Mexico border town of Matamoros — and raised by his mother in a nearby trailer park. He grew up poor and spent his formidable years traversing the country by train, often busking in cities like New Orleans, Dallas, and, by 2009, New York. The latter stop resulted in a short-lived management deal with Sony, but didn’t amount to his big break. From there, Crockett bounced around from California to Europe, sometimes farming and sometimes playing music.

He returned to Texas in 2015, found steady gigs and friends like Bruce Robison — who became his manager and produced The Man From Waco — and Leon Bridges, with whom Crockett will tour this summer on a coast-to-coast run they’re calling “The Crooner and the Cowboy” tour. Along the way, Crockett found plenty of trouble. He was busted for drug distribution. He’s said he nearly derailed his life in a stock-fraud operation engineered by his brother. And there was the open-heart surgery in 2019 that Crockett underwent for a congenital rhythm disorder called Wolff-Parkinson-White syndrome.

In the Lonesome Drifter track “Easy Money,” he manages to cover a wide swath of his life before the song’s crescendo of, “I woke up in New York City without a name/Wasn’t long before I learned the hustler’s game.” In “Life of a Country Singer,” he furthers his story, singing, “I’m riding out to meet my glory/And breaking my damn heart in songs for you.” It’s true: When a heart breaks in a Charley Crockett song, it shatters like glass on concrete.

“What did Waylon say about ‘Are You Sure Hank Done It This Way?’” Crockett asks. “‘It took me 10 minutes to write, but it took me 10 years to think it up.’ There’s a lot of that in my music.”

Crockett recorded Lonesome Drifter in L.A. at Sunset Sound Studio 3, a bucket-list facility for him. When he learned that Shooter Jennings signed an exclusive lease on the studio, he jumped at the chance to work with the Grammy-winning son of Waylon. The two had not collaborated before, but recording Lonesome Drifter went so well that they’ve already committed to the follow-up album. “Charley and I, we’re on some path together,” Jennings tells Rolling Stone.

To Crockett, the producer’s appeal is in his flexibility. Jennings prefers to adapt his approach to the artists he works with rather than put his stamp on a project. It’s the same tactic that won Robison over with Crockett.

“Shooter would hear a song that I was showing him, and I would get ready to throw it away real quick,” Crockett says. “And he’d go, ‘Nope. Let’s cut that.” Or I’d tell him a song wasn’t finished, and he’d say, ‘Yeah it is. What about that song you were playing before that? Put those two together.’ I’d go, ‘Shit, I hadn’t even thought about that,’ and he’d say, ‘Man, Waylon and Willie were doing this all the time.’

Jennings feels he’s at his best in the studio when he’s working off instinct, eschewing pre-production and cumbersome plans. Like Robison had done on The Man From Waco, the approach suited Crockett’s freewheeling mind.

“He’s really wild,” Jennings says. “He crafts the performance and the singing of the verses at the same time he’s writing it, and it creates this interesting molding process that he has. I’ve seen him do it now hundreds of times, and it’s really unique to him.”

Lonesome Drifter also marks Crockett’s debut for Island Records, home to pop stars like Sabrina Carpenter and Chappell Roan, and fellow country singer Wyatt Flores — the closest anyone on the roster comes to Crockett’s background. But where Flores is 23 and in an early-career ascent, Crockett has spent his entire career avoiding a label deal, choosing to release his music independently on his Son of Davy label.

“The reason I’m working with Island is because the things I demanded were release control and creative control,” he says. “They had to do that and get the deal done before hearing anything. And they did it.”

Crockett may view the business with skepticism, but his climb through the ranks of independent music brought him plenty of allies. He once approached the Turnpike Troubadours after a show at Gruene Hall outside New Braunfels, Texas, hoping to share his music with the Red Dirt outfit. Turnpike responded by taking Crockett on the road as an opener for nearly two years. Today, five years after the release of The Man From Waco, there’s a generation of singer-songwriters crediting Crockett as their primary influence. Vincent Neil Emerson — whose “7 Come 11” Crockett covered — is one. Noeline Hofmann is another. The 21-year-old Alberta, Canada, native opened Crockett’s $10 Cowboy Tour last summer, her first-ever tour.

“I’d played hundreds of hole-in-the-wall shows over the years, but the $10 Cowboy Tour was the very first tour of my life,” Hofmann tells Rolling Stone. “Charley took a chance on me, and I got my road legs under me on those shows.

“Charley runs a tight ship and a world class band. He is a workhorse and sets the bar high on and off the stage,” she continues. “He is steadfast in his vision and carves his own track, unbound by the traditional confines of genre or establishment. He is just himself, and to be around that energy is contagious. It inspires greatness. It fires me up to work harder and smarter. Challenge my best. Challenge my band’s best.”

All these factors — Crockett’s relentless dedication to songwriting, the interest from Island Records, and his growing influence — have turned him into a brand, and there are times Crockett leans into it. His primary touring rig is an 18-wheeler decked out with the artwork from Lonesome Drifter, making it a natural piece of marketing on the highway. The rig served as his shuttle to a pair of record-store performances in Austin in March, one day at Waterloo Records and the next at End of an Ear Records. At both, he played short acoustic sets and signed autographs. He also gave away four-song sampler CDs to anyone who wanted one. He’s giving away 100,000 of those CDs this spring, and he credits his wife with the idea.

Away from the stage, though, Crockett is a Texan who happens to have a rags-to-riches story. He and Grace make their home in Spicewood, not far from Willie Nelson’s Luck Ranch. If Crockett is an ambassador for anything, he says, it’s Lone Star path to stardom, one that Nelson perfected in the Seventies when he split from Nashville for Texas.

“The problem with Tennessee is that Texans are foreigners there. They’re strangers,” Crockett says. “It’s different from L.A., where people see me and say, ‘Aw, look, it’s Big Tex!’ because they’re mystified by it out there. Same thing in New York. Those city slickers are intrigued by Texans. But when you’re in Nashville, it only makes sense that the Tennessee folks are going to have favorites. That’s the city they’re going to ride into, to try to make their name. Texas is really far away, and, for whatever reason, the business itself never really grew up. As hard as that is, and as isolating as that is, it can be a blessing in disguise — like Michael Martin Murphey would say.”

Crockett points out artists like ZZ Top and Freddie King, who saw their music take off once they embraced their Texas roots. “What I’m doing out here is, I’m taking my brand of Texas to the world,” he says.

That state of mind was on full display at the Houston rodeo, long before he climbed into the Thunderbird. Before the show, when officials presented both him and Grace with custom belt buckles commemorating his first Houston rodeo concert, Crockett intimated that he had peaked. “Well, I gotta come up with a new plan now,” he said, “because I hadn’t thought of nothing after this.”

The performance itself was, in just about every way, the antithesis of the club and theater concerts most familiar to Crockett’s fan base. NRG Stadium is a football stadium first, and the rodeo takes place on dirt trucked in and spread across the entire field. When the rodeo action ends, a huge stage rolls out to the center of the stadium, unfolding like a Transformers toy into a star-shaped concert centerpiece. With nobody allowed on the rodeo dirt surrounding the stage, the nearest fans — Crockett’s night drew a crowd of more than 52,000 — are still more than 40 yards from the performance. To counter the distance, the stage rotates, and dozens of video boards bring the show to fans in the rafters and luxury boxes. In his hour-long set, Crockett gave them 19 songs. The setlist, while heavy on Lonesome Drifter, spanned music from his entire career. He played “$10 Cowboy” and “Hard Luck and Circumstances” and danced around the stage during his cover of Link Wray’s “Jukebox Mama.”

“This half of the room says Charley Crockett is too country, and this half of the room says Charley Crockett isn’t country enough,” he said before kicking off a solo acoustic version of “Life of a Country Singer,” on a platform that raised him, guitar in hand, high above the stage.

The remark was a nod to a constant, low-grade stream of criticism that Crockett’s down-home demeanor must be a front to win country music fans.

“I played on the street,” he says. “I played on subway cars. I worked on farms and played campfire jams. I worked open mics and learned how to lead bands by playing blues jams. I hustled up money to dress better, to buy myself an amp and an electric guitar, or just buy a drink at the bar. I spent so many years not even being able to afford to do that. But when you start walking further and further out there into view — I call it the mirror — you start looking into the mirror of America. That mirror starts telling you what it sees. For years, I was surprised by the way that I kind of polarized audiences.

“I came to realize, that, when you’re calling it country, the image that I cut — compared to George Strait or someone — I’m controversial,” he continues. “For whatever reason, I bring some pretty strong feelings out of people who see me.”

He closed the concert the same way he closed Lonesome Drifter — with a cover of Strait’s “Amarillo by Morning” before getting back into the Thunderbird, this time with Grace joining him, to make his exit.

After a green room toast with friends, family, crew, and a sizable contingent from Island, Crockett and Grace boarded their tour bus for a three-hour ride to his Austin Rodeo show the next night. Their dog, Billie, had waited patiently on a couch on the bus for the concert to end. This is where Crockett chose to wrap up our conversation, too. “Find me at 1 a.m. if you want to hear the truth,” he deadpanned before muting the television — almost always tuned to a western movie — and sharing his truths for another hour. In the process, he let his guard down enough to offer insight into how he’s processing his leveling-up era. With the Houston show not yet two hours behind him, he was already re-thinking his earlier comment to organizers that there was no place to go from here.

“It’s the biggest platform in Texas,” he says. “But in another way, it’s just the rodeo. They got the fucking fireworks going off and shit, but it’s still just the rodeo. What I really started thinking was, ‘Cool, I’m playing the rodeo, this is a big deal. But you know what would be really hard would be to go back to that stadium and get them all to come out there just to see me.’ What’s in it for me, if I were to make it to a stadium circuit only? I’m not sure.”

That’s also an answer that can wait. For all the places his career has taken him — including a debut on The Tonight Show Starring Jimmy Fallon less than two weeks after the Houston rodeo gig — Crockett isn’t walking around with a five-year plan. He’s wise to the world, but he’s not scheming to get a leg up on anybody. He saw how writing and covering powerful music afforded his Spicewood neighbor, Nelson, a life and career on his terms. That’s why Lonesome Drifter marks three albums in a year and why he and Jennings have another one already holstered. Being a prolific creator has allowed Crockett to flourish in an industry churning out the next big thing by the hour, and it has positioned him to thrive as long as the road will have him.

“I gotta make sure that I can put out records quickly,” Crockett says as the TV flickers behind him on the bus. “That’s the only reason I’m here. I wouldn’t have these buses. I wouldn’t have that truck. I wouldn’t be on this bill. I wouldn’t be working with Island. None of this would have happened if I didn’t put out a lot of records.”

Josh Crutchmer is a journalist and author whose third book, Red Dirt Unplugged, was released in December 2024 via Back Lounge Publishing.