Late last April at a small German beer hall in Queens filled with steins and bolo ties, Charley Crockett took the stage to celebrate the release of $10 Cowboy. Backed by the Blue Drifters, his trusty band by way of Austin, Texas, he played a style of music he calls “Gulf & Western,” an amalgamation of the blues, folk, soul, and country influences he absorbed growing up between South Texas, Dallas, and New Orleans. The New York crowd—unmistakably full of belt-buckled transplants—was captivated, only looking away to two-step. But one look at the man himself and it was clear: Charley Crockett is tired.
At the pace he works, it’d be hard not to be. $10 Cowboy and its recent sequel, Visions of Dallas, mark his 15th album since 2015 and his ninth since 2020. Before that, Crockett spent roughly a decade busking across the northern hemisphere. In New Orleans, he learned traditional street songs and was introduced to the hobo lifestyle; in the Dallas-Fort Worth area, he played honky tonks and street corners alongside Leon Bridges and Vincent Neil Emerson. There were stints in Paris, Copenhagen, Morocco, California, and New York City, where he and his folk-meets-hip-hop group the Train Robbers were discovered performing on a subway car by a music industry executive. Their new manager aspired to take the Train Robbers mainstream; Crockett had other ideas, heading to Northern California to work on a weed farm (and traffic pounds of it) until their contract expired.
Risky as this move was, it allowed Crockett the time and independence to concoct a vintage country sound that still manages to be forward-thinking. The core of his music pays homage to old-school outlaws—Hank Williams, Willie Nelson, and James Hand—but more elastic artists like T-Bone Walker and Link Wray play a role too, attributing to his boogie-woogie and rock‘n’roll tendencies. Crockett’s mix of genres initially confused some country purists, but these roots-driven sensibilities have now situated him alongside contemporary stars like Tyler Childers, Colter Wall, and Sierra Ferrell who are moving the genre forward by looking back. With the $10 Cowboy series, Crockett not only cements that he is one of the most prolific artists in the business, but that he is one of the most consistent, too.
Chapter I, the stronger of the two releases, features one of Crockett’s most personal and well-executed ballads to date, “Good at Losing,” a solemn ride-along through the years he spent traveling aimlessly. The title track, “$10 Cowboy,” is another highlight: a slow burner that traces the similarities between cowboy singers and bull-riders, quixotic showmen eking out an existence on the outskirts of society. This feeling, a desire to be seen but a refusal to be known, runs strong through Chapter I. Crockett takes the role of a lonesome traveler who, despite getting kicked around time and time again, continues to stride towards the blurry paradise he believes America still has to offer.
The bulk of Chapter II is made up of covers, including renditions of Jack Routh’s “Crystal Chandeliers and Burgundy” and Townes Van Zandt’s “Loretta,” two songs written nearly 50 years ago that still speak to Crockett’s troubadour narrative. Crockett has always done a good job at keeping the classics alive, but the album’s originals lack the punch and narrative depth of Chapter I. “20-20 Vision,” off Chapter II, is led by a simple ragtime piano riff and a whining electric guitar that puts his smoky baritone voice in its natural setting: a dusty bar room. It’s a good track, but, as is the case with much of Chapter II, it doesn’t really weave in his relationship with Dallas. Instead, it’s a song that could be dropped nearly anywhere on his discography.
Compared to the intimate showcase of Chapter I, Chapter II comes off more like a grab-bag of Crockett loosies than a true sequel. He’s at his strongest when he writes about the ghosts from his past, battles with redemption and belonging, or pours his heart out for a lover; he retreats to his comfort zone when he falls back on songs about “Trouble and Misery” or invokes casinos as a lasting emblem of false hope in America. Yet throughout both, his conviction and sense of place are undeniable. In the decade it took Crockett to brush country stardom, the bygone era of music he loves and embodies arrived in the modern age. He is a key player in deciding where it will go next.
