Watching Charley Crockett connect dots can be dizzying, especially when they represent moments in his highly unlikely life story. Case in point: last September I met up with him and his girlfriend, Taylor Grace, at Manhattan’s ritzy Park Lane hotel, in their thirty-sixth-floor suite overlooking Central Park. It was a Monday afternoon, and Charley—a 38-year-old singer-songwriter whose singular blend of country, blues, Southern soul, Tex-Mex, and old Storyville styles has made him one of the hottest independent acts in American music—was in the city on big business, to take meetings with major record labels and heavyweight manager candidates but also to open a sold-out Willie Nelson show the next night. As we looked out the window at the park, I searched for the SummerStage area where Charley and Willie would perform. But while I was thinking about tomorrow’s gig, Charley was anchored some fifteen years in the past.

“Central Park is the first place I ever played in New York City,” he explained, pulling me in with his earnest, intense green eyes. “There was this Brazilian dude I grew up with in Dallas, Felipe, who lived in South Florida. I’d been visiting him down there but ended up catching a ride to Asheville, North Carolina, then hitchhiking up here, because Felipe had a buddy I knew, vaguely, with an apartment on the Upper East Side.” Charley crashed at that buddy’s place.

“As soon as I got here, I went looking for a busking spot in the park and found this little jazz band playing,” he said. That was good news and bad. “Every big town in America has the same politics; if there’s a street corner or a subway platform where you can make good money busking, you better believe there’s already somebody there doing it.” So Charley settled for a spot at the north end of a little stone bridge near the Central Park Carousel called Playmates Arch. The money wasn’t much, but it suited him fine. “I made five dollars sitting there for a couple hours. And there was a little nook around the corner where I could smoke weed out of view.

“I was telling Taylor last night how wild it was to be looking out over the park where I started,” he went on. “I sat right here, watched the sunset, and stared at all them blinking lights. Then I got up early this morning and watched the sun rise. And then I started writing a song.”

So goes time with Charley Crockett, the conversational ball bouncing back and forth between the young, itinerant street hustler and the present-day budding rock star. Twenty minutes later, in a cab headed down to Greenwich Village, he was describing a time around 2010 when he and the four guys in his busking collective were squatting illegally in a ten-by-ten-foot Brooklyn rehearsal space—only to stop suddenly and point at a two-story Times Square billboard showing the cover of his latest album, The Man From Waco

Ten minutes after that we were in the Village, standing at the corner of Bleecker and Jones. Onstage, Charley’s an impeccable dandy, partial to sharp, vintage Western threads. For our walkabout he looked like a laid-back Americana heartthrob, guitar case in hand, with a short-sleeved, blue-striped snap-button shirt; stretch-denim Wranglers with two cellphones in the left back pocket; brown pointy-toed boots; a fist-size belt buckle adorned with a ram’s head (he’s an Aries); and a gray felt Stetson with a hard-taco pinch to the brim. He moved to a stoop beside a pet bakery that, from 1983 until 2018, had housed Caffè Vivaldi, which was home to one of the city’s best-known open mic nights. He set down his guitar, peered up at the building, and flashed a broad, toothy smile.

“This was the first venue where I ever sat down to play,” he said, before gesturing north, up Jones Street. “The Freewheelin’ Bob Dylan album cover was shot up there, and there was a little wine shop where I’d go buy a bottle to sit here and drink while I was waiting my turn. I had a hard time getting on that stage. The gal that ran the club wouldn’t do me any favors, because I smelled bad and didn’t have any money.”

As we walked on, he described other obstacles that kept performers without resources—in other words, street people—off open mic stages: onerous pay-to-play requirements such as drink minimums and small-batch, advance-ticket purchases. He ticked off the places he did play, like the Postcrypt Coffeehouse, in the basement of St. Paul’s Chapel, and Lucky Jack’s, on Orchard Street, often mentioning a gracious manager who let him stay on his couch. But Charley punctuated that laundry list with the names of music-biz bigwigs who’d been calling of late, including Coran Capshaw (longtime Dave Matthews Band manager) and Ken Levitan (longtime manager of Emmylou Harris).

He stopped in front of an organic grocery store on Sixth Avenue. “There was a Rasta who worked there making juices upstairs,” he recalled. “He saw me stealing stuff to eat and told me the easier way was to get a plate from the prepared-food buffet, bring it upstairs, then sit and eat without paying. So that’s what I did.”

The story had barely left his mouth when Charley fans started popping out of the pedestrian flow to say “Hey” and request selfies. There was a young couple from Los Angeles, a New York University songwriting student from Minneapolis, and a kid in brand-new square-toed boots, named Eli. As Charley put his arm around Eli for a photo, surreptitiously cocking his own hat to a rakish angle for the pic, a construction worker in a fleet pickup hollered “Charley!” from traffic. “Hey, baby!” Charley hollered back. “Come see me tomorrow night! I’m opening for Willie!” 

But Charley carried his guitar for a reason, and as a slight rain started to fall—he’d looked up and seen it coming; I’d looked up and seen nothing—we jogged for the First Avenue subway station, where he could pick a little. The clock had just hit 5 p.m. “Playing at this hour is tough,” he explained in the knowing tone of a career MTA functionary. “There’s too many trains, and they’re going both ways. You want to be down here between ten a.m. and four, or after seven p.m. Even then, it’s mostly percussionists on pickle buckets. They’re louder and rhythmic. Might even have some dancers with ’em.”

Sure enough, for the next half hour, he received scant notice. Folks were headed home, and the trains roared to a stop, idled loudly, then roared back off every couple minutes. Undaunted, he ran through a batch of songs, and during still moments, it was striking how clear his husky voice sounded against the subway tile. At one point he got a smattering of applause from the far end of the station, and a lone commuter stopped to shoot a video. But no money landed in the guitar case.

Eventually, we boarded a train heading back uptown. The car was too crowded to play, so we stood, held a handrail, and talked. “My roots started showing through when I was in New York,” he recalled, growing pensive. “I started realizing how Texas I was. I had to go a long way to realize that, to see what it was and embrace it. But I tell you, the success I’m enjoying was inevitable. All this s—’s inevitable . . . if you just don’t stop.”

“I suppose it helps if you’re good at it too,” I suggested, blowing some smoke up his Wranglers.

“Yeah,” he replied. “But if you don’t stop, you get good.”

The Long Ride of Charley Crockett
Crockett at C-Boy’s Heart & Soul, in Austin, on March 13, 2023.Photograph by Jai Lennard

Charley is an oddly polarizing figure. You’ve got the fans who stop him on the street in New York. Or who sing along with every song at shows where the main draw is a headlining legend like Willie. Or even the guy who randomly gave me a ride home from the airport when I returned to Austin. Somehow I wound up in a car driven by a cofounder of Vox Media, in town from New York for a conference. He said he’d almost flown back the previous night for the Central Park show but sent his thirteen-year-old son instead. “My wife and I wanted his first concert to be Charley and Willie.” 

But not everybody gets Charley Crockett. When I first started paying attention to him, I found that just mentioning his name could prompt dramatic eye rolls. Some people regard him as akin to a con man. One friend, a hard-core country music lover, dismissively pointed me to YouTube clips of young Charley. The music was old-timey, a jazzy country-blues that sounded almost vaudevillian, often accompanied by a rapper. In subway-car videos he wore a flatcap and suspenders; in later ones from Deep Ellum blues clubs, he had on a fedora and Ray-Bans. To that friend’s mind, Charley was a tourist in country music, his high-style Western wardrobe an unforgivable affect.

Other skeptics focus on the wild improbability of Charley’s backstory, which does read like an overbaked movie script. There’s Charley’s decade spent hitchhiking and train-hopping; his busking apprenticeships in New Orleans, Paris, and rural Morocco; and his life-threatening heart condition and subsequent surgeries. He’s also had high-stakes run-ins with the law: when he was still in his teens, he got involved in a multimillion-dollar stock-fraud scheme, and later, he ran large loads of weed cross-country to finance his earliest recordings. Most folks don’t know anyone who did any of those things. That Charley might have done all of them strikes some listeners as a salesman’s bunkum.

Spend five minutes with Charley and you’ll learn that he’s more than capable of making a sale. But he’s wearied of having to make that one. “Most of the time, I don’t talk about this s—,” he says, “because the ordinary person, they can’t believe any of this happened. They’re just trying to figure out how much of my story I invented. 

“My only plan ever has been two different things: How do I move to a better spot? And how do I get my music in every person’s hand who’s willing to take it?” 

Charley backed into busking by accident. Born in the Lower Rio Grande Valley town of San Benito, in 1984, he spent his first year in a single-wide trailer in Port Isabel with his mom, dad, grandmother, and a half brother and half sister some ten years his senior. His dad soon split, and after his mom found work in Brownsville, she moved the family to the cane fields and grapefruit orchards in nearby Los Fresnos. Money was tight, but music was everywhere, on CDs his mom played—everything from Billie Holiday and Carole King to Bob Dylan and Harry Connick Jr.—and in the country and tejano hits that floated in the Valley air. From the start, Charley was into all of it.

His mom moved the family to Irving, just outside Dallas, when he was nine, but when he discusses his teen years, he talks mostly of New Orleans. That’s where he spent his summers, staying with an uncle, a cook in the French Quarter. Charley’s musical taste broadened to include big band–era crooners his uncle loved and the swamp pop and hot jazz he heard on the streets. When he was seventeen, his mom bought him his first guitar at a pawn shop. She’d just lost her job, and he’s still not sure how she was able to afford it, but he hungrily taught himself to play by ear. Bored one afternoon, with the AC out at his house, he took the guitar to a park, found a bench under a shade tree, and started picking rough blues licks. A passerby mistook him for a working musician and threw change in his guitar case. It’d be years before Charley saw busking as a way out of poverty, but he took note.

In the meantime, he found a way out that almost put him in prison. The closest thing he had to a father figure in Texas was his older half brother. The 28-year-old was a high school dropout and an effective salesman; he’d parlayed a GED and a newspaper delivery job into car sales and, eventually, a stockbroker’s license in Dallas. But he soon got involved in a large-scale pump-and-dump stock scheme. It was a textbook scam, with stock values driven up by unsolicited mass-email campaigns touting windfall opportunities as well as by stock sales between conspiring underlings. Charley’s brother ended up atop one of the scheme’s networks, and he enlisted a nineteen-year-old Charley to help.

The U.S. Securities and Exchange Commission caught on within a couple of years. Charley talks vaguely about the scope of the enterprise and the higher-up players, alluding to hundreds of shell companies, crime families, and international banks that were, in his words, untouchable. That sounds melodramatic. But Charley and his brother were eminently prosecutable. In court filings, an SEC investigator testified that just three of the companies connected to Charley brought in $43.9 million in net trading proceeds. Charley’s brother fled to Costa Rica in 2008 while under investigation, was extradited, and ended up sentenced to seven years in prison. Charley—young, believably naive, and cooperative—managed to avoid jail time.

“At first I was afraid of not knowing where I’d sleep. But eventually you realize the sun keeps coming up. And playing on street corners, turning those people upside down and shaking money out of their pockets . . .” He pauses. “There’s a lot of power in that.”

“After everything came down,” he recalls, “I couldn’t get a bank account for ten years, and I’m not allowed to participate in the stock market for life. Coming from a background where I didn’t have nothing, that drove me to the street. I’d seen behind the veil, and I thought, ‘F— it, I’m going this other way. Punch a clock? Not while I’m young enough to stand on a street corner and write songs for a living.’ ”

He began hoboing, as he calls it, bouncing between Dallas, New Orleans, Northern California, and, eventually, New York. The rules of proper society no longer applied. If an opportunity to go somewhere presented itself, be it in the form of a new friend with a vehicle, an open boxcar, or just the inclination to put his thumb out and hitchhike, he took it, living off busking tips, handouts, and the occasional bit of petty larceny. “I don’t know how to explain how much freedom I found in having faith in the kindness of strangers,” he says. “At first I was afraid of not knowing where I’d sleep. But eventually you realize the sun keeps coming up. And playing on street corners, turning those people upside down and shaking money out of their pockets . . .” He pauses. “There’s a lot of power in that.”

The best money came in New York, but he was always ready to roam. One night in 2009, a Danish jazz singer hanging at Caffè Vivaldi offered to let Charley stay at his apartment in Copenhagen and connect him with club owners. Charley took him up on it, making what he calls “crazy money.” But he grew bored after a couple months and headed for Paris. An Albanian traveler on the train told him to take his guitar to Montmartre and the Sacré-Cœur Basilica. 

The Long Ride of Charley Crockett
In the East Village, circa 2008. Courtesy of Charley Crockett
The Long Ride of Charley Crockett
In New Orleans, on Frenchmen Street, circa 2011. Courtesy of Charley Crockett

“As soon as I got there, I fell in with the Gypsies playing on the steps, who let me join in because I was American. I realized that while I was playing, they’d pickpocket tourists. I was a good distraction.” The tips in Paris dwarfed even Copenhagen’s, and Charley got serious. A local who let him stay in his flat lent him a laptop, and Charley recorded ten songs and burned them onto blank CDs. He clipped photos of models out of a French fashion magazine and used them as cover art, then sold the CDs for five euros when he busked. “I started making way more money immediately, not even from the CDs; I was more legit because I had something to sell.”

He played Paris for a year and then, worried about his long-expired visa, caught a ride to Morocco, eventually making his way to a one-pay-phone village in the Atlas Mountains. He spent some six months there, working the fields in exchange for a room, listening to Berber folk music on AM radio, and playing one-string banjos crafted from gourds and sticks. “That part of Morocco might as well have been in 1910,” he says. “I felt a sense of isolation I’d never experienced. You don’t know if or how you’ll ever get back. But then a longing to get home washed over me, a desire to be recognized in my own country for my art.”

Charley says the culture shock upon returning to New York in 2011 was way crazier than his introduction to Europe and Africa. Life in the Atlas Mountains had felt genuine and timeless; when he’d walked ten miles with his host to a neighboring village, locals had treated him to a freshly slaughtered goat. Back in Brooklyn he found hipsters concerned solely with fashion. “The scenes were all whack,” he says. “The Bushwick warehouses? Williamsburg? That wasn’t about music. It sent me deeper into the streets. That’s when I got into subway platforms.”

He soon found two collaborators who would prove pivotal. The first was Jadon Woodard, a cocky nineteen-year-old spoken-word artist who’d started rapping in Philadelphia train cars a year earlier. Jadon had taken his hustle to New York, and he’d started seeing Charley playing the stations. One day Jadon approached him at a G train stop, free-styling briefly over Charley’s guitar, prompting an uptick in tips that piqued Charley’s interest. Jadon insisted, however, that the real money was on trains. Charley was reluctant, but Jadon kept finding and pestering him. Finally they boarded a subway car. “That first time we performed,” Jadon remembers, “we made some cheese”—by which he meant $300. Charley was in, and trains were the way forward. 

Still, he remained a nomad. When the weather turned, he left for New Orleans, bringing a couple pickers with him while Jadon stayed behind. That’s where he met a trumpet player named Charlie Mills Jr. “One day I was beefing with my girlfriend and needed to clear my head,” recalls Mills, now a middle school math teacher, “so I took my horn to the Quarter to find somebody to play with.” Soon a group of guys with guitars walked up. “I said, ‘Y’all wanna jam?’ Charley Crockett said, ‘Yeah. We’re looking to make some money.’ He was on a mission. He asked, ‘What’s the best corner? What time should we be there? And if today’s not the day, let’s learn some tunes.’ ”

That was the key. A heavyset dude with a trim beard, Mills knew the game inside and out. He had the banter—“We take credit cards,” he’d call out, “but we don’t always give them back”—and knew how to draw a crowd. A favorite tactic was to play quietly but juke a lot; that’d draw curiosity from blocks away. More significant, Mills was an erudite student of music. He was impressed that Charley played originals, but he also knew what tourists expected in New Orleans. 

“He said, ‘Hey man, I got these songs you should learn,’ ” recalls Charley, “and he’d pull out the sheet music to Kid Ory’s version of ‘Bill Bailey.’ It was all these recognizable traditionals: ‘Basin Street Blues,’ that old Yiddish song ‘Bei Mir Bistu Shein,’ drinking songs like ‘Drivin’ Nails in My Coffin.’ He knew that’s what we needed better than I did.”

After a week or so, Charley’s buddies headed back north—in the borrowed car they’d been sleeping in—while he stayed behind to learn from Mills. It was a graduate class in street performing. “That’s when I started wearing suits,” says Charley, “because if you looked dirty, you attracted gutter punks, and that f—ed up my money. Tourists wouldn’t come anywhere near you. I started taking better care of myself so people would respect me.”

Charley had a new set list when he hooked back up with Jadon in New York, and they added a trumpet player to flesh out the combo. “I was like, ‘How the f— are we gonna pull off ‘Bei Mir Bistu Shein’ on a flooded-in train with a black rapper who’s urban as s—?’ ” says Jadon. “But that was Charley’s thing: just try it.”

Now a four-piece billing themselves as the Train Robbers, they hit the cars hard, looping the city for eight hours a day. With the audience changing constantly, they’d work songs over and over, and their sound got tight, as did their operation. Admiring the guerrilla marketing of DIY artists such as rapper Wiz Khalifa, they handed out flyers and mixtapes and had a hype man shoot videos while they played. They created a QR code that linked to a Facebook page.

In June 2012 a music-biz insider who’d seen them on the R train, Nell Mulderry, emailed their Facebook page. She was well-connected; she’d recently brokered a merchandising deal between Sony Legacy, the Miles Davis estate, and streetwear giant Supreme. The band signed a two-year management deal with her, changing their outlook instantly. “She was an old-school gangster,” says Charley. “And I don’t mean that negatively.” She set them up with club residencies, photo shoots, Gibson guitars, apartment sublets, and clothes. 

Charley and Jadon remain convinced that Mulderry would have made them huge stars. But she had a specific idea for their sound. “She gave us a playlist of what she wanted to turn us into: Gym Class Heroes, Flo Rida—which seemed to me like a Maroon 5–type group with a rapper,” says Jadon. “Not to dis any of them, but that wasn’t us.” Charley concurs. “She wanted us to be a street-people boy band.”

Toward the end of summer, the group met at her office to sign a deal they’d set in motion themselves. Someone with the NBC program Talk Stoop had seen them on the trains and wanted them to become the show’s house band. If they’d gotten the gig, they’d have been on national TV, with segments syndicated to taxicab and gas-pump screens around the country. Then suddenly Charley balked.

“He dropped a bomb,” says Jadon. “He said, ‘We talked about it, and we don’t want this NBC deal, and we don’t want to be signed to you anymore. We feel like we’re selling out.’ ” Jadon adds, “I’ll never forget that, because he hadn’t told me anything.”

Charley’s abrupt reversal killed the management deal, the band, and, for the next few years, his friendship with Jadon. They’d reconcile eventually—Jadon, all hugs, showed up backstage at Charley’s Central Park concert. But it took them awhile to get there; Jadon’s still working his rhymes, but he’s never had a deal like that in front of him again.

Charley regrets costing him that break. He also calls their flirtation with the mainstream one of the most important things that ever happened to him. “That got me off the street. I started thinking that if the street hustle just leads to the pop machine—and no control over the direction of my music—what reason do I have to stay on the street? Because the street’s dangerous. I needed off.”

He left for Northern California, determined to save enough money to independently produce a record. He found work on a marijuana farm in Mendocino County—“Mendo,” as Charley calls it—so he went to work there. Too hyper to trim leaves or buds, he started with grunt work, digging postholes and wiring fence. He soon realized he’d need real money to get his career going.

The Long Ride of Charley Crockett
Crockett at the train depot.Photograph by Jai Lennard

The first time I ever spoke with Charley Crockett was in March 2022, when I interviewed him for Texas Monthly’s Willie Nelson–themed podcast, One by Willie. Charley talked that day about an old Willie song, “Face of a Fighter.” It was a nerd’s choice, a 1961 demo Willie never recorded for commercial release. 

But where Charley roped me in was with a vaguely Willie-related anecdote about getting pulled over in Virginia in 2014. He sensed trouble immediately. “They pulled me out of the car . . . and I knew I was going to jail,” he said. “They were making fun of me, these cops.” When they asked where he was headed, Charley said he was en route to a gig. The law didn’t buy it. “They were like, ‘Yeah, boy, you’re a country music singer. I’ll bet you are. Why don’t you play something for us right now?’ ” He grabbed his Telecaster—and froze. “I pulled out that guitar, nervous as hell, and I swear to God the only song I could think to play was [Willie’s] ‘The Party’s Over’ ”—he strummed an air guitar and started singing, “Turn out the lights, the party’s over”—“and they were like, ‘That’s a fitting song, boy.’ Then that dude busted the suitcase open and [found] a bunch of medicinal plants.”

His punch line was ripe with euphemism. In fact, they found six pounds of weed, which actually was fortunate; he’d left Mendo with fifty. That was his plan to fund his first record, running dope to cities where he’d busked. It had started months earlier, with a delivery to San Francisco. “I made fifteen hundred dollars for that two-hour drive,” he says. “That was a lot of money, and it was thrilling. But there was a lot of fear, driving with all that in your trunk. I didn’t even have a license. I was living so far outside society that I forgot myself. I forgot the risk.”

The risk was plain enough now: a felony trafficking charge and at least five years in prison. But timing was on Charley’s side. The exploding meth epidemic and national trend toward legalization had made weed-dealing less of a law enforcement priority. He knew better than to rely on luck, though. After a month in jail, he made bail and returned to Mendo, convinced that his only hope was to build a music career and show the judge he was on a good path. He went to work on his first album. 

Recorded that winter in a cabin on the ganja farm, A Stolen Jewel is a snapshot of his busking sets—a bluesy, jazzy mix of acoustic covers and originals, with finger snaps and claps providing rhythm and Charlie Mills flown in to play trumpet. Charley pressed five thousand CDs and moved back to Dallas to book gigs and find fans. The city, and in particular Deep Ellum, was undergoing a musical renaissance. Hip-hop was the primary style, but blues and R&B are in the soil in Deep Ellum. Charley’s act lit on all three. 

“I started thinking that if the street hustle just leads to the pop machine—and no control over the direction of my music—what reason do I have to stay on the street? Because the street’s dangerous. I needed off.”

His envoy to the scene was guitarist Alexis Sanchez, who grew up in nearby Garland. He and Charley had started going to blues jams together when Charley was in town for deliveries. “Every time I saw that guy,” recalls Sanchez, “he had a different guitar and a different car.” They grew close, and with Sanchez making intros, Charley started playing small clubs such as Adair’s, then jumping onstage at larger venues with acts like a then-unknown Leon Bridges. Soon Charley was headlining his own shows. To get his music into people’s hands, he left gimme stacks of A Stolen Jewel in nightclub men’s rooms. 

He was building momentum but still had real life to contend with. In late 2015 his half sister, Brandy, died suddenly. They hadn’t kept in steady contact in years, owing to his road life and her long struggle with addiction, but he’d happened to see her that summer. In childhood, their bond had been music, and she’d beamed when he played Stolen Jewel for her. When she died, he wrote a song for her, “I Wanna Cry,” then put his head back down. Intent on building the strongest hand possible for the judge, he wanted more recordings.

The centerpiece of his second album, In the Night, was “I Am Not Afraid,” a song he’d written on the fly while listening to Smokey Robinson records in Sanchez’s apartment. With its sunny pop-R&B melody, a bedrock of warm steel guitar, and a skittering, roller rink organ as its pulse, it was a huge leap forward, a seamless blend of the country and Tex-Mex he grew up on, informed by the Motown compositions he’d started studying. (It’s his most listened-to track on Spotify, with more than 20 million streams.) The rest of the album showed similar growth, veering between steel guitar–driven country and Deep Ellum blues awash in Hammond B3 organ. It was nearly finished when he went back to the judge.

“I showed him I’d made strides over the two years it took to get to trial,” says Charley. “I had a CD, Stolen Jewel, that was out and distributed; In the Night, which was damn near a final mix; and a gig at the Granada Theater for the In the Night rollout.” He pleaded guilty to a marijuana manufacturing charge, paid a $10,000 fine, and walked without jail time. Finally, the road ahead was wide open.

Over the next two years, Charley became a touring machine. Based in Austin, he played 280 shows a year with the Blue Drifters, the backing band he’d built around Sanchez. Always wanting new product to sell, he spent whatever downtime he found in the studio, with the idea that he’d release two records a year, aided by a pair of big-wheel players who’d joined his team. Jon Folk, Americana music’s leading promoter, booked his gigs, and David Macias, whose Nashville-based marketing and distribution company, Thirty Tigers, lets artists own their masters, pushed his records.

As Folk’s and Macias’s country connections suggest, Charley’s look and sound were evolving. Gone were the page boy cap and the fedora, replaced by a cowboy hat. On his records, the music—which he’d started calling “Gulf and Western”—still melded his influences. His first album of 2018, Lonesome as a Shadow, was recorded in Memphis and marked by a smoky, after-hours soul sound; his second, the covers collection Lil G.L.’s Blue Bonanza, is heavy on T-Bone Walker and Charles Brown blues. But both records also feature strong country cuts. He’d had songs like that in his live set from the start, such as “Drivin’ Nails” and Hank Williams’s “I Saw the Light.” Now when he played them in Texas—or even out of state, because Texas is where he’s from—the amped-up fan reaction brought to mind Mills’s golden rule: give the people what they want.

“I’d never thought I’d get called a country artist,” says Charley. “Eventually I leaned into it, because that’s what they were calling me. I’d never even heard of Americana in those days. Seriously, I’d only heard the term in agriculture. A breed of chicken. I’m not bullshitting.”

The true coup was a tour slot with the Turnpike Troubadours, who took Charley into thousand-seat halls packed with young country fans. “We opened for those guys on one hundred–something shows,” says Sanchez. “It became a thing: ‘We’re going to see Charley and Turnpike!’ Then we’d see Turnpike fans wearing Charley T-shirts.” In June 2018 they played a transformative sold-out show at Red Rocks, the 9,000-plus-seat amphitheater outside Denver. Charley and his Blue Drifters encountered the same frenzied reaction they were starting to expect, now blown up by a factor of ten. The band started dreaming that the next time they played Red Rocks, some scrappy upstarts might be opening for them. 

Then, that winter, Charley learned that his heart had a defective valve. A doctor told him that if he didn’t have open-heart surgery—and soon—he might be dead in three months.

Charley Crockett Luck Reunion
Charley Crockett performs live onstage during the Luck Reunion on March 17, 2022, in Luck, Texas.Jim Bennett/WireImage

The title track to Charley’s 2019 album, The Valley, is essentially a mission statement, though like the rest of his writing, it’s not prima facie confessional. The era of country music he alludes to most
often is the late fifties to mid-sixties, years dominated by decidedly pre-Dylan, golden-age composers such as Harlan Howard and Hank Cochran. Charley’s sparse lyrics are never cryptic; they’re much more likely to be crafted around an old idiom or clever wordplay, or even be literal. And because they live in songs owing a clear sonic debt to that era, it can be easy to confuse autobiographical notes for period piece tropes. Consider the third verse to “The Valley”:

My daddy didn’t know me

My brother rolled the dice

My mama kept on working

And my sister paid a price.

That’s a true story, a hard one. And Charley ends the song with a moral he absolutely lives by: “May your curse become a blessing / There ain’t nothing else to do.”

He’d written and recorded that song, and much of the rest of the record, in the uncertain weeks between his diagnosis and the operation. “I wrote The Valley as a last will and testament,” says Charley, “but also a prayer. There’s a real fear with that surgery stuff. You become deeply aware of how little time we’re on earth.”

The heart trouble hadn’t come out of the blue. As a kid, he’d been diagnosed with Wolff-Parkinson-White syndrome, a condition that can lead to arrhythmia but that Charley hadn’t ever believed to be dangerous. He’d figured he’d outgrow it. Now 34, he’d attributed recent dizzy spells, his head pounding with each heartbeat, to his hard-charging road life and a hernia he’d developed in Morocco. But after a scary episode at a show in Austin—he’d turned white onstage and fled to the bus; Sanchez found him there later, stripped to his underwear and looking green—he saw a doctor and learned that the bad valve was letting blood flood his right ventricle. Luckily, the surgeries—he ended up needing two—were successful.

He was back on the road after just three months but struggling with a dark depression. His strength and stamina were shot, and his chest ached constantly. His mortality became an obsession. When the tour ended in October, he cut loose his Dallas-based manager and the girlfriend he lived with in Austin. Effectively homeless again, he headed for Mendo, where he spent some nights at friends’ farms and others in his truck. He started writing the songs that would comprise his next album.

That December, Charley recorded Welcome to Hard Times in a Georgia studio run by Mark Neill, who’d won a Grammy for coproducing the Black Keys’ 2010 breakthrough, Brothers. Neill is an analog and roots-music extremist. Intrigued by Charley’s hybrid sound, he’d loaded him up in preproduction with mid-sixties recordings by Waylon Jennings. Old hits like “Only Daddy That’ll Walk the Line” are now considered classic country, but Neill instructed Charley to pay special attention to the way Waylon used a Hammond B3 and a straight, four-four beat. “Waylon took George Jones country and the R&B of the time,” says Neill, “and put them on a blind date. He was trying to merge Motown with the Carter Family.”

Neill’s manic fealty to the old school was a salve that eased Charley out of his funk. New songs such as “The Poplar Tree” may have referenced the scar on his chest and the shadow of death, but he sounded at home in Neill’s throwback setting. Hard Times was his countriest album yet, evoking heroes such as Jennings, Johnny Paycheck, and Marty Robbins. It was also his breakthrough.

But due to the pandemic lockdown, which hit just after they finished recording, that ascent traveled a tortuous path. Worried that Charley couldn’t tour to promote the album, much of his team wanted to delay its release. “Jon Folk was the one who said, ‘Don’t let them shelve your s—,’ ” says Charley. “He said ‘It’s relevant right now.’ ” 

Charley knew Folk was right; just the title, Welcome to Hard Times, made the record timely. He decided to release it in July 2020, confident he could attract radio play, streams, and sales by building word-of-mouth buzz. To do so, he wanted to spend the road budget on billboards and videos. It wasn’t exactly a twenty-first-century strategy. “I pushed Charley to spend less on outdoor advertising,” says Macias, “and Charley said no.”

“I’d come up with the idea to spend two hundred thousand dollars on billboards,” says Charley. “And guess what? We got that money, and I bought billboards in L.A., Austin, Nashville, New York, and Houston. And bro, because of the shutdown they were, like, seventy-five percent off. And instead of staying up for one month, they stayed up for four. And here’s the funny thing: Everybody in L.A. had to leave their house at some point, right? So everybody saw it, from Rick Rubin to Diplo. All those motherf—ers saw it.”

The billboards were effective; not long after they appeared, Charley signed a publishing deal with Rubin, the onetime Beastie Boys hype man who’d become one of the world’s leading record producers. But it was the videos, fashioned as a curious minisuite of musical spaghetti westerns, that blew up his audience. 

The first installment was the title cut, opening with a black screen and the sound of howling wind. Then the picture comes up, a distant view of the Sierra Nevada mountain range. In the middle distance, Charley walks silently up a dirt road, his duster flapping with each step. In the foreground, a yellow rotary phone sits on a small wooden table, no cord connecting it to anywhere. It starts ringing, at which point “Welcome to Hard Times”—which had the makings of a pandemic anthem—starts playing. 

“Using that phone as a MacGuffin was Taylor’s idea,” says Charley, referring to Taylor Grace, the woman he’d just fallen for after a night dancing at Austin’s White Horse saloon. “I started thinking that ring was destiny calling.”

Whatever it was, it worked. The videos went viral. The billboards turned heads through the summer. Against all odds, Charley had turned the whole nation into a subway platform, and the cool kids headed home could not take their eyes off him.

The Long Ride of Charley Crockett
Crockett at C-Boy’s, in Austin.Photograph by Jai Lennard

Charley is a talker. Last October we made plans to spend an hour on the phone on a Thursday afternoon, a conversation that ended up lasting three hours—and three more the next day. Dude’s a born salesman but also a teacher. In both capacities he’s got plenty to say.

He answered the phone Thursday on the porch of a little ranchette he and Taylor bought in northern New Mexico during the pandemic, about halfway between Taos and Colorado state line. They’ve recently been looking to move back to Austin, but through the lockdown, the remote, place-out-of-time locale—area farmers have told Charley that the acequias irrigating their fields are actually pre-Spanish, dating back at least a thousand years—proved a great spot to write songs. 

“I woke up one morning and walked into the orchard with my guitar,” he said. “I had the phrase ‘I’m just a clown’ stuck in my head”—referring to what would be the lead single off The Man From Waco—“and it came to me initially as this old, three-chord, George Jones–style melody in a home key of C. I brought it back in the house midday and on a whim decided to move it to the relative minor, A minor, and flipped it to an R&B beat. Let me show you what I mean . . .” He set the phone down and played the song both ways on guitar, transporting it instantly from an East Texas honky-tonk to a Memphis juke joint. “That’s how interchangeable those styles are. It started with Jones in the morning, and by early afternoon it’s Bill Withers.” 

That transformation comes second nature to him now, but it took years to learn. As a young man playing by ear, he’d simply find chords that fit; nobody ever taught him the basics. “I couldn’t hold straight country chords when I started,” he said. “I remember when I began playing country music in front of people, there’d be all these punk-ass motherf—ers saying, ‘He’s not a real country singer because he’s holding bar chords’ ”—a tuning technique that purists consider a cheat. “Well, Loretta Lynn played bar chords, and I’d put her in the five best country songwriters of all time.”

It’s a topic, namely who’s country and who’s not, that makes Charley bristle—and many country fans as well. Those fans tend to be possessive; whenever the genre evolves, a generation of listeners objects, with great passion, that the new sound isn’t country. Think about the backlash against contemporary bro country from fans raised on Garth Brooks—and then recall the way Garth’s stadium-ready sound rubbed fans brought up on Merle Haggard the wrong way. So when Charley releases a record that doesn’t strictly adhere to the sound of the era he’s quoting, hardliners who love that period scoff. One prominent Texas record producer—who asked not to be identified—told me that Charley bugs him because he’ll do things like cover an old honky-tonk shuffle, but without a straight shuffle rhythm underneath.

Charley’s tired of such gripes. While he’s careful not to put himself in the same league as artists who changed country music by mixing in elements of other styles, be it Jennings with R&B or Willie Nelson with jazz, he’ll indicate they’re precedents. More to the point, blending influences is at the core of who he is. “That’s part of growing up poor in culturally and ethnically diverse places, whether it’s Texas, Louisiana, Georgia, wherever,” he says. “Remember playing Little League baseball? The thing after the game was to fill up on suicides, where you mix every f—ing drink in the soda fountain. We wanted all of it.”

Other, less informed objections often feature a racial, even racist component. Though Charley identifies as white, his great-grandmother was part-Black, and when he was a kid, as his hair darkened from its early blond, people started wondering what race he was. That perceived ambiguity has followed him ever since. “When I played the streets, it would more often be Black people questioning it. They’d get close and say, ‘Oh s—, I thought you were a brother. My bad.’ ” Social media trolls have been significantly less gracious, posting comments along the lines of “Who’s the mulatto?” and “I didn’t know Steph Curry sang country.”

“They say all this s—, like ‘That’s a weird-looking guy.’ Am I really that weird looking? Or is it just that I don’t look like a golden retriever white dude? I don’t know, man. I’ve tried hard to get away from talking about this because I don’t want to come off as playing the ‘marginalized person’ card. I just don’t have that right. Charlie Mills is a dark-skinned Black man. He’s highly educated, and I got no education. Yet when we walked into a grocery store together, he’d be the one that they’d follow around, thinking he was stealing. All he was doing was reading the f— out of labels because he wants to know what’s in anything before he buys it. That wouldn’t happen to me, even though I’m the one with the rap sheet.”

Charley deals with all that by focusing on the music and how he wants it to sound, blocking out not just the haters but often the considered counsel of folks working with him. When Charley got ready to record again, in early 2022, Rubin’s team got excited. They’d been talking for over a year about bringing him to Rubin’s famous Shangri-La studio, in Malibu. Guessing they’d want to invite A-list collaborators in lieu of the Blue Drifters, Charley decided instead to take the band into the Bunker, a Lockhart studio run by Austin singer-songwriter and producer Bruce Robison, who was also his manager at the time. Thinking Charley was merely cutting demos, Rubin’s team promised a list of ten candidates to produce the real sessions. By the time that list arrived, Charley said he liked what he was getting and that Robison would produce, at which point Rubin’s team promised a list of world-class sound engineers to mix and master the finished album. Once that list arrived, Robison had already found an engineer Charley wanted to work with. The result was The Man From Waco, which Rubin’s people acknowledge is Charley’s first masterpiece.

Its sound is distinctly late sixties, with nods to the groovy, go-go boots productions of Lee Hazlewood. The title track is a brooding murder ballad with hints of Ennio Morricone that sounds like the song Charley was writing in his head while wandering the desert in the “Hard Times” video. On the sweetly strummed ballad “Time of the Cottonwood Trees,” you can hear him falling deeper in love with Taylor in the New Mexican wilderness: “She drove a blue pickup truck / Boy, she loved it though it really wasn’t much / Kinda like the way she loved me.” He even gives gripe-ists who think he’s cartoonish a nail to hang their hats on, tacking on cattle-call yelps to the end of each chorus in “Cowboy Candy,” his upbeat ode to pharmaceutical pick-me-ups. 

If critics object, they don’t have to listen. “I read once about this surrealist painter,” says Charley. “A rich couple bought this really provocative painting of his. And they asked him to explain it. He said, ‘If you need an explanation from me, I’d rather give you your money back.’

“At times I feel like that,” he concluded, “because I’m pouring it all into the g—damn songs. I want people to look at me for the music.”

In mid-December, Charley made a triumphant return to Austin, playing two sold-out shows at the 2,750-seat ACL Live theater. The three months since the Central Park concert with Willie had been a heady blur. In October his new manager, Ken Levitan, introduced him to storied roots producer T Bone Burnett, who got him to write and record a song for his next movie soundtrack. Then came a sold-out six-date headlining tour of Europe, followed by a 25-city U.S. tour. At his first-ever show at Nashville’s fabled Ryman Auditorium—which he sold out on a Monday night, no less—he earned a lengthy standing ovation before he was halfway through his set. Ethan Hawke showed up at his Webster Hall show in New York, bending his ear for an hour backstage. Matthew McConaughey tipped his hat in a What’s-on-my-playlist? story in the Nashville Tennessean.

Much of that momentum was driven by Waco, which had started showing up on year-end best-of lists. Rolling Stone deemed it the second-best country album of the year. In early December, Charley made his late-night television debut on Jimmy Kimmel Live! playing “I’m Just a Clown,” which had spent twelve consecutive weeks atop the Americana radio play chart. He’d also booked an NPR Tiny Desk show for January, his first Australian tour in March, Willie’s all-star ninetieth birthday extravaganza at the Hollywood Bowl in April, and a Bonnaroo appearance in June. Oh, and he had plans to propose to Taylor on New Year’s Day. (She said yes.)

None of that was on fans’ minds when he took the stage in Austin. Tickets had been sold out for months, and the diehards’ pent-up anticipation erupted when pianist Kullen Fox played the first notes of “The Man From Waco Theme,” the instrumental dirge that leads off the album.  As the lights came up, the other Blue Drifters came into view, cast against the massive gold-velvet curtain Charley hangs in every hall that’ll let him. He chose it because it reminded him of the one Johnny Cash used on his old variety show.

Out strolled Charley in a wide-collared, brown-suede bolero jacket, gray woolen bell-bottoms, boots, and that trademark cowboy hat. To the crowd’s delight, he followed the opener with five more songs off Waco, starting with “Cowboy Candy.” If anybody in the room made fun of the song’s trail-hand yips, they were drowned out by everybody else, who hollered along like the whole reason they’d come was for that moment.

Charley had them in his back pocket, where he kept them for two hours. The band was loose and high-energy, but the show’s pacing was precise. He talked little between songs, letting his music and movements do the work. Between verses he shook his hips and held his guitar’s body to his ear, its head pointed to the rafters, à la Dwight Yoakam. At other moments he stood rock still and peered down its neck like he was aiming a rifle, another homage to Cash. At one point, he set his guitar aside for two bluesy covers—Jerry Reed’s “I Feel for You” and T-Bone Walker’s “Travelin’ Blues”—stalking the stage with a handheld mic like a Reno lounge singer. Then he grabbed a banjo to play his take on the old railroad workers song “Nine Pound Hammer” and a galloping original, “Round This World,” before switching to a Telecaster for a stomp through his trumpet-heavy tribute to New Orleans’s second-line parades, “Trinity River.” 

At this point he was driving the crowd crazy, two-stepping with his guitar during Sanchez’s solos, leading the band through the high-octane numbers that closed his set and ending on a furious version of “In the Night.” For an encore, he played an update of Bob Marley’s “I Shot the Sheriff” and, finally, a thundering run through “I’m Just a Clown.”

After the show, the Charley organization retired to his favorite Austin haunt, C-Boy’s, on South Congress, for a tour-wrap party. It was a subdued night’s end for the band, who looked ready for a vacation. But the tipped-off fans who wandered in were wound up. While Charley sat ensconced in conversation with Jeanmarie Stokes, a veteran R&B singer who made a small name for herself in Austin clubs in the eighties, admirers gathered in a semicircle around his booth, all waiting anxiously for a piece of Charley Crockett.

He probably ought to get used to that. Because he’s starting to look inevitable.

This article originally appeared in the June 2023 issue of Texas Monthly with the headline “The Long Road of Charley Crockett.” Subscribe today.

Additional credits: styling by Cristina Facundo, Cortney Sprayberry, and Taylor Grace; Grooming by Tara Cooper