There is a distinct kind of mythology that wraps itself around Charley Crockett. With his sharp vintage suits, effortless brand of cool and a worn acoustic guitar slung over his shoulder, he looks like a ghost pulled straight from a 1950s honky-tonk. But behind the polished veneer of the Texas troubadour lies a story far more complex, rugged and untamed than any country song could hold.
Now, a new documentary and concert film, A Cowboy in London, aims to strip away the myth and show the man. The film, which premiered at the South by Southwest (SXSW) Film Festival earlier this month, offers an unfiltered look at the beloved blues and country singer. The film follows the journey of a rising star of Texas music, yes, but it also follows the story of the Texas filmmaker who caught him on tape.
Much like Crockett himself, director Jared L. Christopher knows the Dallas-Fort Worth sprawl intimately. Growing up in Grand Prairie, a sort of middle ground between the two, he understands the invisible geographic lines that define North Texas.
“If you grow up in Dallas, you really never go to Fort Worth. And if you grew up in Fort Worth, you never go to Dallas,” Christopher says to the Observer. “I identify with Dallas when people ask me where I’m from.”
That local soil is exactly where his connection with Crockett took root. Crockett spent a significant chunk of his early life in Irving and honed his musical craft busking on the streets of Deep Ellum.
“Me being from Grand Prairie, we actually knew some of the same people, so we stayed in touch,” Christopher explains. “When you hear his voice, there’s only one Charley Crockett. When he sings, you know who it is every time. And so, I was just taken by him, and I thought, well, we need to work together.”
Charley Crockett takes London (and the big screen) with A Cowboy in London.
The path to premiering a film at the State Theatre during SXSW was not a straight line for Christopher. His journey started in the trenches of local journalism as a video journalist for the Fort Worth Star-Telegram. He recalls hustling just to get a taste of the Austin festival scene.
“I had convinced my editor to let me cover South By purely for the badge,” he admits. Tagging along with the paper’s former film critic, Cary Darling, Christopher used his credentials to slip into just about any room he wanted.
“Just in the back of my head, I thought, one day I’ll have a film that’ll premiere here,” he says.
On March 18, that thought became a reality.
Honest, Not Polished
A Cowboy in London is a bold departure from the standard, sanitized music documentary. It does not exist to merely stroke an artist’s ego or sell records. Instead, Christopher wanted to create something honest and meaningful — a film that had something real to say. Inspired by the old-school vérité documentaries that both he and Crockett admire — works by Les Blank, D.A. Pennebaker, the Maysles Brothers — Christopher’s approach was all about capturing truth, not hype.
“This is going to upset some people, but this is real and we need to put this out,” Christopher says about the film’s unflinching gaze. “It is [Crockett] laid bare for the audience to decide how they feel. And to me, that’s what a documentary is. Otherwise, you’re making reality TV, and so we’re trying to resist that at every impulse.”
Documentary filmmaking of this caliber requires immense patience and sharp instincts. Christopher describes his creative process as a delicate balancing act of observation and presence.
“I’m always trying to find that place where the version of you that you think exists, and the version of your friends and family that speak of you, sort of meet,” he notes. “I try to find that middle ground, and that can be uncomfortable.”
Capturing that fleeting medium is no easy feat.
“This type of filmmaking is without a doubt the hardest type of filmmaking, and it’s because you only get one shot at it,” Christopher says. “It’s literally observing and also being present and sharp enough to capture these moments that only happen once.”
Part of Crockett’s truth involves a history that occasionally casts a long shadow over his soaring success. Recently, the singer made headlines when he was denied entry at the Canadian border due to an old drug conviction, forcing him to cancel a string of international shows. It was a stark reminder that the hard-traveling, outlaw persona is not a marketing gimmick — it’s a lived experience with real-world consequences.
Christopher views these moments with the empathetic but objective eye of a true storyteller.
“I won’t speak for him, but certainly he’s got a past,” Christopher says. “And as [Crockett said in his social media post], that came back to haunt him there at the border. When you live that kind of life, you certainly have a past, and sometimes that literally comes back to haunt you.”
Fans often romanticize the drifting, busking lifestyle that Crockett endured before finding fame. But the reality of sleeping on the streets and hustling to survive leaves deep scars. As Christopher points out, “So many people question parts of his story. The truth about his story is probably even darker than people realize.”
Yet, it is precisely this darkness, woven with an undeniable star power, that makes Crockett such a magnetic force. He carries the weight of his past onto the stage every night, channeling it into a sound that feels entirely out of time.
After A Cowboy in London screened at the State Theatre to close out SXSW’s film portion, the celebration spilled over into the night. Crockett took the stage at Stubb’s Bar-B-Q in Austin to perform alongside fellow Texas musicians Presley Haile, Nicky Diamonds and Calder Allen.
But on a screen in a darkened theater, audiences witnessed Charley Crockett stripped of his armor, laid out bare through the lens of a local filmmaker who knew how to look past the Stetson.
A Cowboy in London is not available on streaming or in theaters yet.