Charley Crockett spends so much time on the road, he says he sleeps better on his bus than on a real bed.
"That big diesel motor sings me lullabies at night," he says. "It really is comforting to me. You know, the low hum of the motor and the satellite television, turned down low on some old-time movie."
In the last year, Crockett played more than 100 shows — in Australia, Canada, the U.K. and all over the U.S. And his preference for the bus, he says, explains why there isn't a whole lot in this dressing room backstage at the Yaamava' Resort & Casino in San Bernardino. The counters are sparse — a bottle of mezcal, a bowl of lemons and ginger, a bag of tortilla chips and a case of Topo Chico.
"I take the lemon and I just squeeze it into my mezcal there," he says. When asked if the mezcal is good for his singing voice, he replies: "Yeah, let's go with that."
Outside the dressing room, in a hallway lined with signed cymbals, his wardrobe trunks are cracked open, filled with exquisitely preserved vintage Western wear — a collector's dream. There are Pendleton and houndstooth jackets, and smooth golden leather ones with fringe and elaborate stitching. He pulls out a box of beautiful tan cowboy boots, with cream-colored rodeo riders in mid-flight on the side.
"I bet I paid too much for these," he says. "I started dressing up on the street in New Orleans. And the main reason was, being [the] hobo that I was, I started dressing up so the tourists would take me serious, you know? Back then, I was wearing wingtip shoes and old newsboy caps. I used to do a little jig for the tourists in front of Café Du Monde." He breaks out into a jig in the carpeted hallway. He's still got it. "I was a song-and-dance man."
Crockett is still a song-and-dance man. But he's come a long way since his days busking on the streets of New Orleans. Now, he performs at theaters in front of thousands of people. He's graced the stage at Nashville's legendary Ryman Auditorium, and he's jammed with Willie Nelson. He even got married at Willie Nelson's Luck Ranch last year. To cap it all off, he's up for his first Grammy, for Best Americana Album, for his record $10 Cowboy.
Crockett says family lore links him to the frontiersman and politician Davy Crockett — "Son of Davy" is written on big red letters on his touring truck. He was born in the state where Davy died, in San Benito, Texas, just miles from the Mexican border in the Lower Rio Grande Valley. He spent his early years living near there, in a single-wide trailer with his mom, among grapefruit and orange groves, cotton and sugarcane.
Crockett recalls being influenced at an early age by The Johnny Canales Show — the musical showcase helmed by the eponymous Tejano singer — and Crockett says he used to get up on a milk crate, sporting a cape, swing his arm and shout "Take it away!" to repeat the host's signature line.
When he was 8 or 9, his mom moved them up to the Dallas-Fort Worth area. It was around then that he began to spend summers down in New Orleans. He lived with his uncle, who worked as a bouncer at strip clubs on Bourbon Street, dealt cards at casinos and worked the bingo halls.
"I was seeing the culture of the French Quarter when I was 8, 9 years old," Crockett recalls. When he was older, he started playing and singing on the streets there. "And it really was in New Orleans where I learned all the different styles. I learned drinking songs, playing in front of tourists on Royal Street. I got a sense of jazz timing, of how to really strum a guitar, how to pick a guitar to a two-beat, to a shuffle. I'm not a jazz musician by any stretch, but I learned some jazz positions to substitute in for simple country and blues chords, there on those streets, you know?"
It was also in New Orleans that he says he learned to play for an audience; how to entertain and talk to crowds — a skill that he finessed in New York City, playing in the parks.
"I was playing in the spot nobody wanted," he says. "And then slowly but surely, over a couple of years, I started getting better, you know, because I was playing 10 hours a day. But I couldn't compete with the noise of the traffic, just one young man and a guitar. It pushed me underground."
Underground, to subway platforms and inside train cars. He began performing with a group that called itself "Train Robbers," and in one video, you can see Crockett, in a beanie and black T-shirt, singing soulfully as his friend Jadon Woodard raps between verses.
Performing in New York brought other opportunities. He drifted to California, Colorado, Copenhagen, Paris and Morocco to busk. But the farther he got, he says, the more he felt his Texas roots showing.
"I think I was running from Texas for a long time. Eventually, you run far enough from home that you realize at some point that, even in trying to get away from it, it tells you who you are."
They laughed at me in New York City
Called me a fool in L.A
I doubt that Nashville saw me coming
Besides the bar folks working late
Played every room in the state of Texas
All the ones in California too
So many nights I can't remember
Maybe I've played a song for you
Left San Francisco in a hurry
They ran me out of Fort Worth town
Been to the bottom of New Orleans
Them river boats make a lonesome sound
— "Good at Losing," from the album $10 Cowboy
As he takes the stage for the soundcheck at the Yaamava' Theater, he's sporting a pale buckskin jacket, plaid Western shirt and relaxed fit jeans. He's got on a big white cowboy hat, and his initials loom large over the band, the two Cs sideways horseshoes, studded with lights.
In addition to Crockett's exhausting tour schedule, he's released a prolific amount of music. He's put out 15 records in the last nine years, all on his own label, Son of Davy. In March, he's putting out another, Lonesome Drifter, co-produced by Shooter Jennings, the son of Waylon Jennings and Jessi Colter.
In the middle of it all, in 2019 he underwent open-heart surgery, for a potentially fatal heart valve problem. But even that hasn't slowed him down.
"I think with my heart surgery, when I woke up on the other side of it, it's not the pain or the scar on my chest — it was that all of a sudden I realized that I was going to die," he says of what he took from that.
If anything, it's made him work harder. He's afraid to stop, he says.
"I guess I'm afraid of getting fenced in, you know? As you move further into this business, the ticket sales go up. The ticket price goes way up. I can tell you, it puts a pressure on you to be like, 'Well I need to do something more.'"
It sounds a bit like he's saying "making it" as an artist means constantly feeling inadequate — like you're not enough.
"I didn't mean to put it like that. But I mean, you could just say that's what it feels to be American, right? That's what we're taught to do. You know you got to work. You got to swing that hammer. And you know what? I'm not mad about that. I'm gonna keep swinging that f***ing hammer," he says.
It might even win him a Grammy.
"I'll give it to my mama if I ever get one."
Ailsa Chang and Kira Wakeam contributed to this story.
Copyright 2025 NPR
