Former Dallasite Charley Crockett is in the midst of what may be the biggest week of his career to date.

On Wednesday, he shared the stage with Dwight Yoakam and other top acts at the Roxy Theatre in Hollywood for a concert benefiting Children’s Hospital Los Angeles.

On Sunday, he will attend the Grammy Awards, where he’s nominated for best traditional country album for Dollar a Day, competing with Willie Nelson, Lukas Nelson, Margo Price and Zach Top. He also contributed to A Tribute to the King of Zydeco, which is up for best regional roots music album.

Then on Thursday, it’s off to the red carpet premiere of his new documentary, A Cowboy in London, at the prestigious Santa Barbara International Film Festival.

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Despite the stack of glowing reviews and accolades, Crockett downplays the attention, placing more importance on the art itself.

Michael Hogue

Crockett has always worked on his own terms. Speaking on the phone from his home in Austin, he discussed his career trajectory and his view of the music industry.

“All that’s going on with country music, I think it’s just a catch-all for people looking for something genuine. That’s what country music is to me,” he said. “There’s an element of country music that speaks to people with rural backgrounds, and I think that’s why it speaks to all of America, because many of us come from a rural background.”

The early days

It wasn’t an easy start for Crockett, now 41. He spent much of his life scraping by, beginning with a childhood in a San Benito trailer park in Cameron County — the southernmost county in Texas — where he was raised by his single mother. When he was 8, they moved to Irving.

“When I was a teenager, my mama got me this guitar out of a South Irving pawnshop. I taught myself how to play by ear, and played everywhere I could,” Crockett said. “They used to do this little guitar pull called Irving City Limits, and I played there a lot.

“Some of the first places I remember walking into were the Sons of Hermann Hall when I was 18, playing my idiosyncratic tunes, and the Balcony Club, when they had that little four-by-six stage by the door. I’d play at the Winedale Tavern, which is now the Single Wide. The smoke was so thick in that place, you couldn’t see the door. Everybody in there looked like they had one foot in the grave, but it was a cool place.”

Crockett attended high school at Carrollton’s R.L. Turner but did not graduate, instead leaving to travel and pursue music. Homelessness was a frequent reality in his teens and 20s as he hitchhiked and hopped trains across the United States and Europe, taking whatever work he could find as a farmhand by day and performing music for spare change at night.

A well-dressed man

Today, Crockett is regarded as one of the best-dressed musicians in country music, a far cry from his vagabond days, when money was scarce and his wardrobe showed it.

“Back when I was playing the streets in New Orleans, I realized that I looked like s— and people didn’t want to come near me,” Crockett said. “The Salvation Army had these brown bag specials on certain days of the week. You could fill a brown paper grocery bag for five bucks,” he said.

Michael Hogue

Over the years, he’s encountered music industry figures who tried to shape him into something he’s not. He talked about one such New York deal.

“They wanted to lock down publishing, bring in an entertainment lawyer and basically to try to mold you into what they want you to be,” he said. “They were showing music videos of all these groups, and they’re gonna decide your name. I was feeling like I had no voice in the situation.”

He ultimately walked away from the deal. As he did, someone in the management group made a last-ditch effort to keep him signed:

Michael Hogue

“I’ll never forget that,” he said. “I was definitely afraid of going back into the streets and staring down the uncertainty of living hand-to-mouth again. But it was one of the best things that ever happened to me. I realized that the less I took control of my own destiny, the more these business types were going to decide it for me.”

Moving back to North Texas

When he moved to Dallas around 2013, he was able to reunite with his mother, whom he hadn’t seen for a couple of years. She’d moved from Irving to East Dallas, and she’d been worried about him, he said.

“From what I remember, the music scene in Dallas had been pretty down and out for a number of years, but it was coming back,” Crockett said. “There were always open mics, and you could feel that it was a revival. That’s when I first met my lead guitar player, Alexis Sanchez, playing at places like Adair’s and the Free Man.”

Sanchez introduced Crockett to Leon Bridges that year, in Bridges’ hometown of Fort Worth.

Michael Hogue

Bridges and Crockett played 16 concerts together last year in a tour dubbed “The Crooner and the Cowboy.”

Becoming a bandleader

Early on, Crockett operated as a one-man band, and it took him several years before he learned how to lead a group. As he traveled the country, he often jumped in with local house bands, learning through trial by fire. Sometimes it clicked; other times it was a train wreck.

“Sometimes I’d get lucky, and the guys on stage could maybe follow me without me saying anything,” he said. “And sometimes I’d get banned from the place. They’d tell me, ‘Don’t come back here until you can lead a band with a blues song and tell everybody what f—ing key you’re in.’”

Momentum began to build for Crockett in 2014, when he formed the band The Blue Drifters with guitarist Sanchez, a Dallasite. The lineup expanded starting in 2016, releasing albums that blend old-school country with blues and soul.

Michael Hogue

Crockett did not use the band on his 2015 debut album, A Stolen Jewel, instead recording the record with Kyle Madrigal, who’s now in the band but was not a member at the time.

The band took clearer shape in 2016 with In the Night, which featured Alexis Sanchez on electric guitar and added Nathan Fleming and Kullen Fox. Percussionist Mario “Mayo” Valdez, a Dallasite, joined at the start of 2018, coinciding with the release of Crockett’s fourth studio album, Lonesome as a Shadow.

Michael Hogue

Crockett has performed many in-store sets at Good Records in Dallas. One of those shows, organized by the late co-owner Chris Penn, took place the same week Penn fell, suffering a spinal injury that left him paralyzed from the neck down.

I spoke with Alex Montenegro, the manager of Good Records, about the impact of Crockett’s frequent appearances at the store.

Michael Hogue

“I miss that man,” Crockett said of Penn, who died in April. “He became one of my biggest advocates in the record store business, maybe the biggest one.”

The documentary

Michael Hogue

A Cowboy in London presents an unvarnished portrait of Crockett on the cusp of global stardom. It traces a chaotic week in London marked by three sold-out shows at Hoxton Hall, unscripted media stops, restless city walks and quiet moments with his fiancée, Taylor Grace, a singer-songwriter from Alabama, whose personal camcorder footage threads through the film.

The film’s director, Fort Worth-based Jared Christopher, began his career as a journalist, spending a decade writing for the Fort Worth Star-Telegram before transitioning into documentary filmmaking.

“If I’m going to do this, I have to have creative control,” Christopher told Crockett. “I’m totally open to your input and suggestions, but this can’t be a commercial for you.”

After completing the rough cut of the film, Christopher sent it to Crockett, then waited more than a week without hearing a response.

Michael Hogue

While Christopher was waiting to hear back from Crockett, he received a text from Taylor Grace saying the film was “like watching a scary movie.”

“That’s not the reaction I wanted,” said Christopher. “But to her point, it’s so raw when you’re the one in front of the camera. This isn’t what we’re used to seeing, which is usually a very curated thing.

“It was really hard to watch,” Crockett said. “And I had a hard time sleeping, actually. That’s part of why I didn’t answer him for a while.” But ultimately, Crockett didn’t ask to make any changes to the film.

Crockett admitted to The Dallas Morning News that he felt underprepared for the Hoxton Hall shows, being a little rusty after not performing solo in some time. “I should’ve done a couple of warm-up solo shows before going to London,” he said. He also spoke candidly about having had a little too much to drink before the second night’s performance.

Before the third show, Jimmy Page showed up and met with Crockett backstage, professing his admiration.

“When Jimmy showed up, I couldn’t believe it. As we were talking, I kept thinking to myself, ‘What is he doing here?’” Crockett said. “Then he started kinda whispering in my ear about how Lightnin’ Hopkins was his first and greatest influence, and talking about playing in New Orleans when he was younger. I felt the respect that he had for Texas and Louisiana music.”

Then Page shared another memory with Crockett from his early days with Led Zeppelin:

Michael Hogue

“After he said that to stuff me, I was less nervous and I let my guard down,” Crockett said. “During the show, it was wild looking up there, seeing Jimmy Page watching me from the balcony. I had my best show of the London sessions that night.”

While in London, Crockett was fitted for his wedding tuxedo at Davies & Son, a prestigious tailoring house that has dressed the British royal family.

A few months after the final cut of the film was completed, Charley Crockett donned that tuxedo as he married Taylor Grace on the ranch of his friend and mentor, Willie Nelson.

Located on the ranch is a historic landmark, the Old West-style town of Luck, built by Nelson as a movie set for Red Headed Stranger.

Michael Hogue

“We’re all here, and it’s just one big jamboree,” Crockett said.

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