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Charley Crockett strides into Studio 3 at Sunset Sound on a recent morning like a guy who’s never lived a day without long legs. Dressed in a brown leather jacket, crisply pressed blue jeans and a cream-colored cowboy hat, he sticks out his hand and says, “I’m Charley with an –ey,” then flashes a roguish grin.
Crockett, a prolific country-music singer and songwriter from the southernmost tip of Texas, has been camped out here at this storied Hollywood recording studio as he works on an album with producer Shooter Jennings. And though they tend to start their sessions pretty early, last night the two musicians and their wives did it up at Dan Tana’s, the clubby Italian joint favored by generations of showfolk.
“They didn’t know me the first time I went in there — they just saw Big Tex walking in, and they gave me so much s—,” Crockett says of his go-to restaurant in Los Angeles. “I went back again later, and the bill was like 800 bucks. I tipped the waiter 100% and wrote ‘Texas money’ on the receipt. Next time I saw that motherf—, he was turning backflips.” He laughs. “That, in a nutshell, is the entertainment business.”
Crockett would know: He’s been tangling with the industry in some form or fashion since one insider saw him as a would-be pop star more than a decade ago.
Now, at age 40, he’s set to release a major-label debut for Island Records that happens to be his 15th LP: “Lonesome Drifter,” a gorgeous set of soulful, lightly psychedelic country-blues tunes he cut last year at Sunset Sound with Jennings, whose father was the late outlaw-country pioneer Waylon Jennings. (Yes, they’re already working on “Lonesome Drifter’s” follow-up.) Renowned for hosting the likes of the Doors, Prince and Neil Young, the dimly lighted studio is jammed today with Crockett’s gear, including two drum kits he’s got set up to record a cover of the song “Bad Company” for a tribute album honoring the British rock supergroup of the same name.
“I signed my Island deal on this organ here for good luck,” Crockett says, running his fingers along a weather-beaten keyboard. “They do it all digital now, but I made ’em print it up.”
With his deep voice, his vintage clothes and his attraction to tales of antiheroes and outsiders — some of them informed by his own run-ins with the law — Crockett wasn’t always in sync with a mainstream country scene dominated by bros in backward ball caps. Yet the genre’s enormous commercial success has created space for more idiosyncratic artists and attracted record labels from the coasts on the hunt for the next Zach Bryan or Jelly Roll.
“Ten years ago, there was no place for me in the broader business,” says Crockett, who came up releasing his records independently. “But it’s kind of like Marlon Brando said in the movie ‘Burn!’: ‘Ten years can be a very long time.’”
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“Lonesome Drifter,” which intersperses Crockett’s originals with handsome renditions of country chestnuts like “Jamestown Ferry” and “Amarillo by Morning,” shares a devotion to tradition with music by Tyler Childers and Sturgill Simpson even as it showcases Crockett’s larger-than-life persona.
“Charley’s got an aura that’s unmatched,” says Leon Bridges, a longtime friend and fellow Texan who’s set to play the Hollywood Bowl with Crockett on June 5. Bridges describes his pal’s fashion sense as “’70s western meets ’90s infomercial” and insists the look isn’t a fa?ade. “It’s a lifestyle for him,” he says.
Reckons Island co-Chief Executive Justin Eshak: “To me, he’s somewhere between Larry McMurtry and Charles Bronson.” Eshak, who helped break Chappell Roan and Sabrina Carpenter last year, thinks of Crockett as an “underground legend” steeped in Texas culture and history yet identifiable to anyone as a figure worthy of attention. “You see him and you’re just like, ‘Who is that guy?’” Eshak says.
A descendant, he says, of the legendary frontiersman Davy Crockett, Charley Crockett grew up poor in Texas’ Rio Grande Valley along the body of water known for centuries as the Gulf of Mexico but which President Trump now refers to as the Gulf of America.
“F— that,” Crockett says of Trump’s attempted rebrand. “I was born on that gulf, and it’s 95% Latino down there. I ain’t never gonna call it that.”
As a teenager, Crockett taught himself to play guitar and write songs and began playing on the street in New Orleans, where he spent the summers with an uncle. He also let his older brother recruit him into an elaborate financial scam for which they both got busted; his brother went to prison while Crockett was barred for life, he says, from participating in the stock market.
Eager for a reset, he hit the road as an itinerant musician-slash-hustler, logging time in Dallas, Paris, even Morocco before landing in New York, where he formed a group called the Train Robbers that performed a mix of roots music and hip-hop on the subway (and on YouTube). In 2012 the outfit linked up with a well-connected manager who wanted to turn the Train Robbers into a kind of multiracial street-kid boy band, as Crockett recalled to Texas Monthly; he eventually quit and headed to Northern California to work on a marijuana farm — only to get pulled over with six pounds of weed in his car.
After spending a month in jail on trafficking charges, Crockett recorded his 2015 solo debut, “A Stolen Jewel,” and moved back to Texas to make a name for himself on any stage that would have him. The progress was slow but steady: In 2021 he was named emerging act of the year at the Americana Music Awards; in 2023 he appeared alongside Snoop Dogg, the Chicks and Kris Kristofferson at Willie Nelson’s 90th birthday concert at the Bowl; last year he landed a song on the hit soundtrack to “Twisters” and scored a Grammy nomination for his album “$10 Cowboy.”
Crockett met Jennings somewhere in there when they both played the same festival. “I can’t remember which one,” Crockett says. “It’s all the goddamn ganja.” Jennings, who’s won three Grammys for his work with Brandi Carlile and Tanya Tucker, is similarly fuzzy on the specifics. But he remembers Crockett’s performance: “I’d never seen anybody with a sound that dialed-in,” the producer says.
For “Lonesome Drifter,” the pair sought inspiration in the music of Bill Withers (who recorded his first LP at Sunset Sound) and in classic westerns like “Hud,” which starred Paul Newman as the cynical son of an ailing rancher, and Sergio Leone’s pulpy Dollars Trilogy. They finished the album before Crockett went into business with Island; in fact, he says, the label signed him without having heard it — a crucial show of loyalty after his professional frustrations with the Train Robbers.
“Charley doesn’t let anybody walk over him,” Bridges says, “and that comes from just getting out there in the field and doing it with no machine.”
With a major label now behind him, Crockett stands to reach new listeners with his vibey sound and his flashy style — “at least if Island does their f— job,” he says with a laugh. But there’s also sure to be interest in his colorful history, about which he’s conflicted. His experiences shaped him, he acknowledges, but talking in detail about some of them “risks hurting people that I’m related to” — not least his brother and his mom, who he says is still haunted by his sister’s death 10 years ago from a drug overdose.
“She’s never gonna be over that,” he says. “I got other people in my family whose backgrounds are coming up, and they’re really worried about it.”
The way Crockett sees it — Jennings too, for that matter — outlaw country “isn’t about the trouble you’ve been in,” he says. “It’s about artistic freedom and creative control.” And anyway he’s got his qualms about being compared too directly to the likes of Willie and Waylon.
“I’ll never hold a candle to those guys,” he says. “They both picked cotton, you know what I mean? I was born in the middle of cotton fields and sugarcane fields. But nobody was picking that s— manually in the ’80s. That generation, they’re just stronger.”
Asked where he envisions Crockett potentially breaking through, Eshak says, “I’d never rule out the idea of country radio. But sometimes there’s a whole song and dance that accompanies that, and it’s unlikely Charley’s really gonna play.” Touring will continue to be important, adds the exec, who says he could also see a future in film and television for Crockett and his wife, musician and stylist Taylor Grace, whom the singer married last fall at Nelson’s Luck Ranch near Austin. (At Sunset Sound, Crockett wears a necklace with a silver pendant that spells out her name.)
“The two of them as a couple have this old-school kind of Hollywood glamour,” Eshak says.
Crockett, who’ll headline the Houston Rodeo on March 17, pays perhaps more attention to showbiz than some in country music. He dug what Timothée Chalamet had to say at last month’s SAG Awards when Chalamet won the lead actor prize for his portrayal of Bob Dylan in “A Complete Unknown.”
“The thing to do now is to pretend you don’t care, and I just love that Timothée was talking about Brando and Viola Davis and how he wants to be great,” he says. “It means he cares about art and about having something to say, and that’s what we need.”
Behind Crockett, a whiteboard leans on the studio wall scrawled with the titles of 28 songs he’s recording for his next record — Vol. 2, he says, of a planned Sagebrush Trilogy he’s modeling on Leone’s film series and on Cormac McCarthy’s Border Trilogy. He admits he’s unsure whether he should include all 28 or tighten the tracklist.
“There’s just so much good stuff,” he says. “I’m a late bloomer. I’ve got some catching up to do.”
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