Two albums into “The Sagebrush Trilogy,” the traveling Texas musician is following his own path to artistic freedom and writing his best songs ever.
Charley Crockett was up there in the sun and sweat and dust of the Jackson, Wyoming, rodeo grounds at the Teton County Fair, letting it all hang out —as a performer and a poet. Watching him strut across the stage, slinging his guitar and belting out very personal songs in his singular style, it struck me as strange that some folks have a hard time figuring out Charley Crockett.
Crockett roaming the mountains of Southwest Montana.
The man is deep, but he’s not complicated. It’s all right there, for anyone who is listening. The street performer background, his bluesy bandleader boogie, a sound that’s as Texas as a hot, dusty wind. And as a songwriter, Crockett brings an unmistakable authenticity and clear-eyed truth to his taut tales of exploited cowboys and transient musicians, Music City double-crosses, and sleazy hucksters.
Charley Crockett knows who he is, and now, two albums into a planned trilogy produced by longtime friend Shooter Jennings, he’s winning a “crooked game” and earning the artistic freedom to chase his visions. No surprise, the free and true Charley Crockett is making the best music of his career.
Charley Crockett can’t be anything other than himself, and while he is his own cat, he’s also an open book.
On stage in Jackson, Wyoming.
Before his raucous and rolling show in Jackson, Crockett invited me into his tour bus for a drink and chat. We’d met earlier in the summer, watching Indian relay racing, at a benefit show he played with Jamie Johnson in Whitefish, Montana.
We spent a couple of hours in Jackson sipping mezcal and talking about rigged systems, getting married on Willie Nelson’s ranch, working on cannabis farms, busking on the subway, Waylon, Cash, Dylan, and much more.
“CRUCIFIED SON”
We were catching Crockett on a summer tour supporting the two albums he released in 2025, Lonesome Drifter in March and Dollar a Day in August.
Crockett has packed a lot into his years in this business, recording an impressive 15 studio albums — some real good ones, too, all with a few great songs. For most of his career, the music industry didn’t know what to do with Crockett, and he was always working with restraints.
But since signing with Island Records, and hooking up with old friend Shooter Jennings to produce, Crockett is finally free to be fully himself.
Crockett about to spin Dollar A Day.
How he got there comes down to one thing for Crockett: “I’m strong enough now, especially, and thank God, because of the people,” he says. “My fans. There’s enough people who know about me who I feel like get me.”
In addition to prolifically recording albums, Crockett remains a touring musician leading his hot band, the Blue Drifters, through swinging shows all across the country. He’s built up a passionate following, especially among younger fans.
When I saw him in Montana and Wyoming, people traveled from all over the West to catch his shows. At the fair and the Indian relay races, Crockett spent plenty of time checking out the scene and visiting with folks. It’s a long way from playing for strangers on the street.
“DOLLAR A DAY”
Crockett’s origin story is well-known at this point. He grew up poor in Texas, raised by a hardworking single mom who did the best with what she had. There were hard times and tough circumstances, but eventually his loving and encouraging mother gave him a guitar, which changed everything.
“I was pretty much always playing in public,” Crockett says. “I didn’t want to play in that little tiny-ass apartment condo that my mom and I were living in. So I went out and played at the park, just sitting on the bleachers banging away on that thing.”
Then Crockett hit the road. He spent years as a street performer, a busker, an open mic night regular, an itinerant musician, roaming the lost highway. He squatted, hitched, worked on cannabis farms. But he was always singing and picking, playing with fellow travelers, performing for whoever stood in front of him. He learned how to write songs and be an artist live, on stage or up against the wall, in a thousand bars and honky-tonks, slinging shrink-wrapped CDs and getting by.
Cruising around Montana with Billie, the Chihuahua, who does not like strangers on the tour bus.
Eventually Evan Felker, of the Turnpike Troubadours, picked him up off a street corner in New Braunfels, Texas, near San Antonio.
“I was still panhandling out in front of Mozie’s and didn’t even know Evan,” Crockett says. “I had heard of Turnpike, but I didn’t know them and didn’t know Evan. By the way everybody was acting when I gave him a CD standing there in the bar, I realized he was somebody, but I didn’t put it together until later that they were headlining Gruene Hall and I couldn’t afford to get in there. Not long after that, I was on the roster and opened it up. Then I opened up for the Turnpike Troubadours like 130 times. I got on that South circuit —I used to call it the Hank Country Chitlin Circuit. It’s the Red Dirt Circuit.”
“LONE STAR”
No one likes to be categorized by others, but it really galls Crockett, an artist intently focused on being his own true self, whatever that is, and succeeding in the music business on his terms. He seems rightly confused that there has been so much discussion about who he is, where he belongs, what to call his music, if he’s “country” enough or “too country.” It doesn’t make much sense to me either, but I’m the kind of person drawn to artists who drink deep from all of American music and combine it into something fresh. If you must label Crockett, “Texas musician” is a good place to start. From bluebonnets and broken-down cowboys to swinging steel pedal and brash horns, Crockett’s music is deeply branded with the Lone Star sound. Crockett calls it “Gulf and Western.”
“You’re underrated culturally as a Texan,” Crockett says, “yet you go to L.A. and New York and they’re fascinated by you. I feel that class barrier with being a Texan in general when you’re dealing with the coastal business machine, but what attracts them to us is that there’s such a clear, distinct Texas identity.”
What he really is, Crockett says, is a blues singer.
“My favorite country singers are the ones who are bluesy. When I first started showing up, playing in bars, in Dallas, in Houston, or even when I was playing on the street and rolling into blues jams, that’s when I started to learn how to lead bands and play elec – trified. I was jamming with this older generation of blues players, and that’s great training for being a bandleader.”
“AIN’T THAT RIGHT?”
Crockett’s well-earned artistic freedom has him creating the best music of his career. A Dollar A Day is full of great songs, with a unique vibe of gritty country funk.
Crockett showed me a long list of short audio clips he had recorded on his phone in the preceding days. “I’m at my best when I’m grabbing creative ideas, playing with them, and turning ’em into a song, following where it goes. Then I visualize a story around it, which is like Kristofferson said, ‘partly truth and partly fiction.’”
On hearing Lonesome Drifter, Island Records told Crockett it reminded them of a Cormac McCarthy story.
Crockett at the Wilsall, Montana, rodeo grounds.
“‘That’s a hell of a compliment,’ I said. But then he was like, ‘Man, you should do a border trilogy.’ And I thought, Here’s my chance. Shooter was into the idea, and it went from there. Looking at McCarthy’s Border Trilogy, the Dollar Trilogy. [Mickey] Newbury’s American Trilogy.”
The result wasn’t necessarily a narrative through line but more like a thematic thread running through that feels like one related epic.
“One of the great things about Willie’s Red Headed Stranger album for me is how highly visual it is,” Crockett says. “You can see these Western portraits in color —images that just cut through and hold. It’s a big story, like a western novel, like Louis L’Amour. That’s the inspiration behind the Sagebrush Trilogy.”
“TENNESSEE QUICK CASH”
As an artist, Crockett says the most important thing he’s done is “defended who I am. Mostly I’ve avoided really bad mistakes that compromise who you are as a person when dealing with a business opportunity where you have people saying ‘Hey, we can fast-track you. Here’s some easy money.’ Because most of what you get in this business is a broke-dick deal.”
Crockett told tales of slick Hollywood agents, with offers to sell his soul.
“They’d see me play, look me up, see that there was a way to leverage me. They’d get a record exec or a big manager to contact me. Next thing you know, I’d get a folder sent to me of a complete album that some ghostwriter had written, and they just wanted me to sing it. They plug me right into the machine. This wasn’t that long ago, right there at the Sunset Marquee in the bar. That shit happens all the time.
“Then there are the producers who don’t get you,” Crockett says. “I had one, from the first moment I walked in there, who wanted me to mix together hip-hop and hard rock with country. I was like, ‘F–k you.’ If there’s one thing that I can’t do, I can’t run into y’all’s world, make some weird electronic mashup, screwing with what I built. I’ll lose everything.”
Crockett is quick to explain that it’s not because he has anything against crossover music or mashups.
“I’m not against that stuff,” he says. “A lot of people make a lot of great music with that. But I don’t know much about that end of the business. That’s not me. It’s about taking chances while still being authentic to yourself.
“Take ‘Lonesome Drifter,’” Crockett says. “That’s a wild song, but it’s me. The guitars, the tremolo, the lead stuff and all that, that’s all me. The band is live. No, this stuff ’s not being concocted by loops.”
“EL PASO TO DENVER”
Crockett and I spend a lot of time talking about life in the Rockies. I live in Southwest Montana, and he’s spending some of the summer in the area. He jokes that Montana promoters have him because they know how much he loves playing the state.
We’re talking about a favorite venue, the Old Saloon, in Paradise Valley, above the Yellowstone, in Emigrant. “I went up there in my late teens with some guys I knew in high school, some real derelict types,” Crockett recalls. “We didn’t have any money, but we came up to Yellowstone, and we were stealing fuel on the way up. We were so broke we were stealing beers out of the gas station.”
His smile fades.
“Shit, I’m embarrassed at how we were running when I was younger.” He’s quiet for a moment, then continues, smiling again.
“I’ll never forget we had this cabin reserved, a basic Forest Service cabin that you can get a good deal on. It was the first time I ever went up 89 and laid eyes on Montana and Paradise Valley, and one of the first places we ever pulled into was the Old Saloon. I just thought, What a cool dive bar. Now I love playing there.”
Things have certainly gotten better for Charley Crockett. In 2024, he married the woman who he says “keeps him grounded,” Taylor Grace. After six years together, they tied the knot on the ranch of Crockett’s friend and mentor, Willie Nelson.
There have been some hard times. In January of 2019, Crockett nearly died (on one of Willie Nelson’s former tour buses—“The Redheaded Stranger,” of all things) and needed two heart surgeries because of a problem with one of his heart valves.
“I woke up and they had implanted a new valve from a cow,” he says. “And I thought, thank God it’s a cow, not a pig. I mean, who can say I’m not a cowboy anymore? F–k you. I’m literally part cow.” He laughs.
His song “Welcome to Hard Times,” released in 2020 during the pandemic, struck a nerve and was a huge hit. “To a lot of people it sounded like this throwback, a nostalgic act,” Crockett says. “But it was real and authentic; the lyrics were deeply personal for me.”
For the most part, though, life is good for Charley Crockett.
Crockett is rightfully proud about his popularity and financial success. “It’s a good feeling. Sometimes it’s like Pretty Boy Floyd, and maybe it’s going to end in a hail of gunfire. That’d be all right, too. But I do feel like I’m known by enough of the ‘real people.’ When I’m in any town—if I go up to Bozeman, if I’m down in South Texas, if I’m in California, if I’m in the upper Midwest, or Pennsylvania—they know me. And that’s a good feeling. It feels like, because of the way that I come up, I’m one of them.”
“AGE OF THE RAM”
Proud Texan that he is, there has been no bigger success to Charley Crockett than playing the Houston Rodeo.
“I mean, George Strait. Selena. It was my biggest life goal at the time,” he says.
“I was like, Wait a second. I don’t know whether or not this is what I want for myself, but the next step would be to sell out that big old stadium,” Crockett says. “I’m really unsure about that. There was a manager pitching me, a friend of mine, and he said, ‘Charley, the goal for you has got to be arenas and stadiums. Any f–king swinging dick that’s not a total dumbass can do it.’ And I thought, Man, if that’s true, that’s so strange. It’s not that I don’t want to do it. Part of me for sure wants to reach as many people as possible.
“They keep calling me the hardest-working man in country music,” Crockett continues. “I’m proud of that. But then in another way, it’s a way of calling me a blue-collar touring country and western artist that is never going to be breakthrough at a certain level.”
For Crockett, it’s about more than the numbers. “For Dylan and Buffet and Willie and them, I think they understood that printing the legend is different than becoming the number. These days, it’s the No. 1 streaming, the No. 1 ticket sales. I’m not writing that off. That’s hard.
Crockett cutting up: shooting pool at Stacey’s in Gallatin Gateway, Montana.
“I told Shooter, Like, OK, and no shade, but there’s a lot of guys selling crazy amounts of tickets. Making a lot of money, maybe more money than I’ll ever see. But does it last? Is it real? Legacy is what matters.”
Crockett sees legends like Nelson, Jimmy Buffett, Johnny Cash, and Loretta Lynn as role models for artistic independence and authenticity. “They were people who sold crazy amounts of records, but they did it their way,” he says. “They got bloody breaking through the wall that they’d built around Nashville.”
We could hear the crowd swell outside the bus as the start of the show grew near, but Crockett still felt like talking about Bob Dylan.
“Dylan’s the reason I went to New York City. This little Jewish dude from those Minnesota mining towns. He’s like the most f–king outlaw punk. He’s a goddamn Woody Guthrie rebel in the hills, and they just can’t smoke ’em out. Nope. They just couldn’t smoke ’em out. Nobody could ever handle ’em or pin ’em up either. No, he’s f–king magic. The whole time I’ve been chasing after him.”
“DIE WITH MY DREAMS ON”
Crockett clearly sees that being out there on the road, a touring musician, is key to his legacy and his creative energy.
I’m not trying to walk the line. I’m just on the road. And that is a hard way to go.
“I’ve been all around this country and this world,” he says, “and I shake every hand and talk to folks and listen. The other night we were having a good time with folks at the rodeo, and I said to Shooter, ‘Living this life, the life of a traveling musician, I’ve realized that there’s so many people with different points of view, with their stories of their trials, and that no one cares about for the most part, or they feel that no one cares.”
Crockett thinks about it for a moment. “I’m not on the left. I’m not on the right. I’m not trying to walk the line. I’m just on the road. And that is a hard way to go.
Crockett remembers the first time he laid eyes on Montana, Yellowstone, and Paradise Valley.
“But then here’s this guy who has connected with my songs, and he’s getting a chance to talk to me, telling me his story. There’s so many f–king angles, we’ll never get all of those ordinary hardworking people to agree on everything. They’re going through some serious trials and tribulations, and what can I do but try to understand them and acknowledge them?” Crockett asks. “I got them boys running out the Dairy Queen who’ve been in the oil field most of their life, and then I got young mixed kids who tell me that they feel seen. What am I supposed to say?”
But now it’s Crockett’s turn to pour his heart out. We finish our drinks, and he gets ready to do what he’s been doing most of his life: stand before the people, singing and playing, sharing his trials and tribulations, openly and honestly, for the pleasure of the crowd.
PHOTOGRAPHY: Jesse Ilan Kornbluth
From our November/December 2025 issue
