Charley Crockett grows into country's legendary traditions with new album '$10 Cowboy'

Americana Music Association 2023 Entertainer of the Year nominee Charley Crockett has graduated from leading a hand-to-mouth existence as a road-weary busker to living for nearly the past half-decade a much more comfortable, hand-to-tour-bus reality.

"$10 Cowboy," the San Benito, Texas, native's latest album, marks the beginning of another era in his life and career.

"I've gone from being rough enough around the edges to having a foot on the street, having everyone around me paid in marijuana, not thinking much of myself or my music and scared ... of success to being a country soul performer making songs for people who appreciate not having to adapt to the limited choices music industry gatekeepers offer them," says Crockett to The Tennessean, backstage before a Saturday night appearance at the Grand Ole Opry.

Life as a 'cowboy singer'

A press release describes the album as a series of "raw, personal, vivid portraits of a country in transition," penned at casinos and tour bus stops and observing the two decades of gentrification that has overrun the "weird" set of venues, like The Continental Club, that were the social and economic hub of the South Congress Street section of Austin, Texas. He spends most of his time in Texas when he's not touring.

Take these notions into consideration when hearing the title track on "$10 Cowboy" or the album's lead singles "Hard Luck and Circumstances" and "Solitary Road."

Then, pull back and look at Crockett's emergence over the past decade from being considered "a pure street musician uncontaminated by radio" to an artist obsessed by "cultural and political things that I'm still learning how to touch that inspire me" and led him to release enough music to "defend myself from definition while I'm figuring this musicality out."

The album's title alludes to a notion that cheapens and limits an artist's growth from a street performer into a modern-era, stadium-headlining country star.

Among many opinions Crockett has, he assuredly has one about the crush of popularity country music is currently experiencing nationwide.

"As much as America's obsessed with identities and politics, there's something else that, when it comes down to it, the people are actually buying," he says.

"Country music is cool right now," he says, then dives into a note about how he feels educating the broadening fanbase to the value of a balance and respect between the work of cowboys who solely hold microphones instead of those working fields is necessary.

"However, as an archetype and identity currently, the cowboy singer is a part of the still-amateur reality of what people are currently accepting as country music. As this movement perseveres and struggles into a harder (more 'professional') reality, the importance of how we think about cowboy singers is going to be much different than it has ever been."

'The pressure's mounting'

Crockett is very much a star but not quite yet a superstar. Given that he's now managed by Grammy-winner Ken Levitan, who has worked with Kenny Rogers, Kid Rock, Meat Loaf and Hank Williams Jr., among others, it's less a matter of how — not if or when — he'll be a larger-than-life personality at the leading edge of country, Western, and rock 'n' roll.

Because he correctly views his career at present through an unprecedented lens, it is the "how" of his forthcoming success that worries him.

A hundred years after Gene Autry's similar fate, Crockett now sits incongruously at a singing-cowboy crossroads of sorts.

Notably, Autry's two decades spent as a North Texas rancher and telegraph operator working midnight shifts made the 40 years he spent as a Country Music Hall of Fame, Hollywood Walk of Fame and Nashville Songwriters Hall of Fame-level actor, television pitchman, musician, radio personality and live performer feel authentic.

On the surface, Crockett's aesthetic and parts of his rising popularity are similar to Autry's. However, dig deeper, and he's similar but wholly different than Autry, Rogers, Herb Jeffries, Glen Campbell, or any "singing cowboy" country star ever.

The singer-songwriter often recalls a moment early in his career when a record industry executive told him that an artist's career typically spanned three records in seven years. "$10 Cowboy" is his 14th in nine years.

It's the culmination of two decades of evolution from playing a guitar his mother bought him at a pawn shop to having albums on top of Americana's charts for most of 2023.

"The pressure's mounting," says Crockett, jokingly.

Whether at Nashville's Opry, at nearly two-dozen festivals worldwide, or celebrating Willie Nelson's 90th birthday at the Hollywood Bowl, Crockett has become an expected fixture at theater showcases holding anywhere from 5,000 to 20,000 people. Onstage as a solo act, 2024 finds him barnstorming at venues greater than they are smaller, playing three shows weekly through October.

Even though a decade's worth of vintage suits and timeless songs feel comfortable with his humanity and presentation, he's still emotionally fidgeting with the power of falling into a lineage as America's next suave, cinemascope and spotlight-ready "singing cowboy."

Crockett recalls sitting in a Parisian cafe seven months ago and being asked if "donning a cowboy hat was an earned American and Texan rite of passage."

His reply speaks volumes.

"Like a lot of things in America, wearing a cowboy hat allows you to assume the perception of earned privilege," he says. "However, my privilege to wear my hat comes through hard circumstances and playing on street corners and in subways. Stepping into the boldness I learned from that, or learning the shapes and positions of the rhythms while playing in New Orleans, to playing every night these days — that's how I earned wearing my hat."

'A high, unclassifiable art that distills everything'

Crockett correctly frames the conversation's lens before The Tennessean can ask about his musical inspirations of late.

He's currently between an album that presents him singing soulful country tunes like George Jones backed by a Stax house band in 1973 and another one in the can that was inspired by the folksy, blue-collar soul of Bill Withers' 1971 debut album — and much like that record and others, including Prince's "Purple Rain," the Rolling Stones' "Exile on Main St.," the Beach Boys' "Pet Sounds," Linda Ronstadt's "Don't Cry Now" and Janis Joplin's "Pearl" — recorded at Hollywood's Sunset Sound Studios.

"I can't sleep at night if I'm not a step ahead of the thousands of people whose eyes I see in these crowds worldwide now."

It wasn't Memphis' Stax, but Austin's Arlyn Studios into which Crockett stepped to record "$10 Cowboy."

Aryln is a 7,000-square-foot facility in which Ray Charles has recorded and where numerous star-studded events have occurred during Austin City Limits and South by Southwest. The space is housed in a place that from 1977 to 1992 was known as Willie Nelson's Austin Opera House, a venue that hosted everyone from Merle Haggard and the Eagles to Tina Turner and Blondie.

"I needed a room big enough to put a 13-person live band playing inspired performances," says Crockett.

It was at Nashville's Ryman in November 2022 that his band showcased how, via their mastery, "country songs have evolved into Cajun ones, Western songs are R&B, honky-tonk anthems are gut-bucket funk bombs, two-steppers become waltzes and ballads become 'Quiet Storm' radio format-ready grooves."

He walked into the studio with emotional concepts and ideas for words that, once blended with his players' work, could grow the album past feeling potentially constrained by the idea that he saw himself settling with fitting into a box as an unwitting "outlaw country" performer.

"Gospel singers, horns, strings — they're all on '$10 Cowboy' because as much as I understand that everyone wants to have an idea of 'what I am' these days, I'm just trying to maintain what I believe to be music as a high, unclassifiable art that distills everything."

'The honest, inspired truth'

In 2024, country music in popular culture can look and sound like both Beyoncé and Dolly Parton, Post Malone and Jelly Roll, Luke Combs and Morgan Wallen, or Kacey Musgraves and Lainey Wilson.

For many reasons, though, country music styles gaining widespread renown could eventually reach the tipping point of popularity and disdain.

However, the century-long archetype of the singing cowboy currently targeted, slightly incongruously, at Crockett's career has proved resistant to prolonged dislike in the American marketplace.

He's conscious of the moment at which he's arrived.

"The weight of my words is finally as powerful as the stereotyping of my image," says Crockett. "People who used to look at me like a freak show realize there's something greater happening inside of me. I deserve to be a spoke in the wheel of (what's gaining momentum right now).

"I'm no longer a desperate young man excited by the machine of popular music. These days, I'm disciplined, mature and pursuing the honest, inspired truth."

This article originally appeared on Nashville Tennessean: Americana star Charley Crockett releases new album '$10 Cowboy'