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Where to Next, Charley Crockett?

The breakout roots singer built a career on hard luck. Now he has to get comfortable with success
Charley Crockett
(Credit: Bobby Cochran)

If you didn’t know better, you might think Charley Crockett is settling down. It’s a Tuesday morning in January, and the Texas singer-songwriter sits at the kitchen table of the house he owns in the mountains of New Mexico with his fiancée, Taylor, to whom he got engaged earlier in the month. There’s a fire in the fireplace and it’s been snowing since he got up, before the sun had even risen.

“I’m going to do something I don’t usually do,” Crockett says, his gravelly Cajun drawl sounding muted and thoughtful over the phone. “I’m trying to write all these songs down. Like write them down on paper, because I never write anything down.”

Usually, he doesn’t have time for such extravagances. The ever-prolific country and blues artist at one point played up to 250 shows a year with his band, the Blue Drifters, and released a dozen albums in the past seven years. He says he has over 2,000 voice memos of unfinished songs on his phone and is set to hit the recording studio before January is complete.

“It’s always just been by memory, just an oral thing,” Crockett says of his past approach to cutting records, the most recent of which, 2022’s The Man From Waco, reached No. 1 on the Americana Music Association’s Albums chart and landed on a slew of year-end critics’ lists. “The songs that have gotten on the albums have just been the ones I remember the best by memory.”

Charley Crockett
(Credit: Bobby Cochran)

Crockett’s journey to this point sounds like it was pulled from one of the traditional folk ballads he learned as a 17-year-old cutting his teeth busking on the street corners of New Orleans. Now 38, he grew up poor, raised by a single mother in south Texas, spent time in jail for weed possession, lived for years as a semi-vagrant musician, and claims to be related to frontiersman Davy Crockett. He even had to undergo emergency surgery in 2019 to cure a potentially fatal heart condition. “It’s funny,” he says, “I think people are drawn in by the live show. But I think some people are maybe interested in me because of that wild background. It seems, you know, almost impossible.”

In another unlikely twist, Crockett got the attention of none other than Willie Nelson, who called him personally to join his Outlaw Music Festival Tour in 2022. “He said, ‘Hey man, I’ve been watching. I’m really proud of you. You want to play some shows?’ And then he handed the phone to his agent,” Crockett recalls. Now he shares that same agent with Nelson and his hero, Bob Dylan, and will join Nelson for his 90th birthday bash at the Hollywood Bowl in April.

As much as he’s been fueled by that itinerate lifestyle — not to mention the romance of riding the rails, à la Woody Guthrie — Crockett needs to get away from it at times. Thus, the home in the mountains. (He splits his time off the road between here New Mexico and Austin, Texas.) “It was always [spend], like, half the year up in the mountains, or on a farm, in order to make myself whole,” he says — and to keep what he calls the “dangerous spirit world” of the streets at bay.

All that hard living seems to have finally paid off: In 2021, he won the Emerging Artist of the Year prize at the Americana Music Honors & Awards, and last year appeared on Jimmy Kimmel Live! and CBS This Morning‘s “Saturday Sessions.” Crockett will make his Bonnaroo debut this summer, as well. “Actually just hearing all those things listed off, I guess I hadn’t even realized,” he admits. “When you put it that way, it makes it sound really good.”

Charley Crockett
(Credit: Bobby Cochran)

Crockett can be forgiven for sounding skeptical. Never getting too comfortable in any situation, knowing that the bottom could always fall out, is hard-wired into him: “I watched my mom live her whole life that way. And she took it on the chin. And she’s still working her ass off, nearing 70,” he says. Seeing her example, though, he adds, “gave me the will to persevere.”

Having Taylor in his life — a singer and stylist who Crockett describes as an “all-around artist” — has helped assuage some of those fears.

“That’s definitely really helped me to have trust in something, beyond just the art. The one thing I’ve always believed in was the art, was the song,” he says. Yet, he harbors a certain lack of faith in his own songwriting abilities, even after sharing a credit with Dylan on “Tom Turkey,” his reimagining of a song sketch from 1973’s Pat Garrett & Billy the Kid soundtrack.

“I think I’m a natural at interpreting other peoples’ material,” he acknowledges. “[But] I don’t see myself as a good songwriter. I guess I’m just not satisfied.”

Someone as restless as Crockett may, in a sense, never be fully satisfied. There’s always someplace else to get to, be it in a spiritual or creative sense. And no matter how big the crowds at his shows get, there’s also an allure in the past, of those days playing on a milk crate outside the venue instead of on the stage inside.

“I’d be lying to you if I told you I didn’t sometimes fantasize about being back in that place, where I was hand in mouth and there wasn’t anybody else involved — just me and the guitar,” Crockett says, with the wisp of a laugh at the very notion. “The only thing that’s changed is there’s a bigger group of people around me. [But] I could easily just be that guy.”