Is Charley Crockett country music’s next big 40-year-old thing?
Charley Crockett confidently enters Studio 3 at Sunset Sound on a recent sunrise like a man who’s always been blessed with lengthy limbs. Sporting a brown leather jacket, pristine blue jeans, and a cream-colored cowboy hat, he introduces himself as “Charley, with an ‘ey’,” followed by a mischievous smile.
Country music artist Crockett, hailing from Texas’ southernmost region, is currently stationed at this renowned Hollywood recording studio, collaborating on an album with producer Shooter Jennings. Despite usually beginning their sessions early, they decided to unwind at Dan Tana’s, a popular Italian eatery that has been a favorite haunt for entertainers for many years.
The first time I visited my favorite spot in LA, people didn’t recognize me; they just saw ‘Big Tex’ entering and treated me poorly, as Crockett recounts. Later on, when I returned, my bill was an astonishing 800 dollars. I generously tipped the waiter 100% and scribbled ‘Texas money’ on the receipt. When I encountered that individual again, he was performing backflips. Laughing, Crockett sums up, “That, in essence, encapsulates the entertainment industry.
I’ve got quite a bit of experience under my belt – I’ve been navigating this industry for well over a decade, ever since someone saw potential in me as a budding pop star. Crockett, with his years of involvement, certainly has the knowledge and insight we can rely on.

Currently at the age of 40, he’s all set to unveil his major-label debut with Island Records – which is his 15th studio album titled “Lonesome Drifter”. This album, filled with soulful and slightly psychedelic country-blues tunes, was recorded last year at Sunset Sound, where he collaborated with Jennings. Interestingly, they’re already working on the sequel to “Lonesome Drifter”. Notably, this studio has previously hosted legends such as The Doors, Prince, and Neil Young. Today, it’s bustling with Crockett’s equipment, including two drum kits, as he records a cover of the song “Bad Company” for a tribute album dedicated to the iconic British rock group by the same name.
Crockett mentions that he sealed his ‘Island deal’ with a touch of superstition by signing it on this old keyboard,” he adds, tracing the keys with his fingers. “Though everything is done digitally today, he insisted they produce a physical copy.
Crockett, with his rich baritone, old-fashioned attire, and fondness for narratives about unconventional characters, some of whom stemmed from his past legal entanglements, didn’t always align with the mainstream country music scene, which was mostly populated by guys wearing baseball caps backward. However, the genre’s massive commercial prosperity has paved the way for artists with unique styles and caught the attention of record labels from the coasts, eager to discover the next Zach Bryan or Jelly Roll.
Ten years back, I didn’t have a spot in the larger corporate world, shares Crockett, who initially self-released his records. However, as Marlon Brando put it in ‘Burn!’, “Ten years can feel incredibly long.

Music
Wesley Schultz, a member of the Denver-based folk-rock duo, has earned the admiration of artists such as Zach Bryan and Noah Kahan.
Title “Lonesome Drifter” blends Crockett’s authentic tunes with charming covers of classic country songs such as “Jamestown Ferry” and “Amarillo by Morning.” This music, much like that of Tyler Childers and Sturgill Simpson, cherishes tradition while also highlighting Crockett’s larger-than-life character.
According to Leon Bridges, a close friend and fellow Texan who’s performing with Crockett at the Hollywood Bowl on June 5, Charley has a unique style that stands out. Bridges compares his friend’s fashion to a blend of ’70s western attire and ’90s infomercial styles, and emphasizes that this is not just a pretense. Instead, he says, it’s a reflection of Charley’s way of life.
According to Justin Eshak, one of the co-CEOs of Reckons Island, Crockett is reminiscent of a blend between Larry McMurtry and Charles Bronson. Eshak, who played a role in introducing Chappell Roan and Sabrina Carpenter last year, considers Crockett as an “underground legend” rooted deeply in Texas culture and history but instantly recognizable to all as someone deserving of notice. “When you see him,” Eshak adds, “you can’t help but wonder, ‘Who on earth is that man?’
Charlie Crockett, it’s claimed, hails from a lineage tracing back to the famed frontiersman Davy Crockett. He spent his childhood in poverty in Texas’ Rio Grande Valley, an area historically recognized as the Gulf of Mexico, but more recently referred to by President Trump as the Gulf of America.
Crockett expresses his disapproval about Trump’s new branding. Born in the Gulf region himself, he emphasizes that it’s predominantly 95% Latino there and vows he will never refer to it by the name suggested.

During his teenage years, Crockett taught himself how to play the guitar and compose songs, performing on the streets of New Orleans whenever he spent his summers there with an uncle. Additionally, his older brother persuaded him into a complex financial scheme, leading them both to be arrested; while his brother served time in prison, Crockett claims he was forever banned from engaging in stock market activities.
Yearning for a fresh start, he embarked on a journey as a traveling musician and entrepreneur, spending stretches of time in cities like Dallas, Paris, and Morocco before eventually settling in New York. There, he established a band known as the Train Robbers, who played a fusion of roots music and hip-hop, both on the subway and online. In 2012, this ensemble joined forces with a prominent manager aiming to transform them into a diverse group reminiscent of a street-kid boy band, according to Texas Monthly; however, he eventually left and moved to Northern California to work on a marijuana farm – an endeavor that led to his arrest for possessing six pounds of cannabis in his vehicle.
Following a month in jail due to trafficking allegations, Crockett launched his solo debut, “A Stolen Jewel,” in 2015. Subsequently, he returned to Texas with aspirations of gaining recognition on any stage that would accept him. His journey was gradual yet consistent: In 2021, he received the title of Emerging Act of the Year at the Americana Music Awards; in 2023, he shared the stage with Snoop Dogg, the Chicks, and Kris Kristofferson at Willie Nelson’s 90th birthday concert at the Bowl. Last year, he secured a song on the popular “Twisters” soundtrack and earned a Grammy nomination for his album ” $10 Cowboy.
Crockett crossed paths with Jennings at some point during their shared participation in a music festival. However, Crockett can’t recall the exact event, attributing it to excessive marijuana use. Similarly vague about the details, Jennings, a three-time Grammy-winning producer for Brandi Carlile and Tanya Tucker, recalls Crockett’s performance distinctly: “I’d never witnessed anyone with such finely tuned sound,” says the producer.

The duo drew inspiration for “Lonesome Drifter” from the music of Bill Withers, who debuted his first album at Sunset Sound, and classic western films such as “Hud,” featuring Paul Newman as a disillusioned rancher’s son, and Sergio Leone’s gritty Dollars Trilogy. They completed the album before Crockett entered into business with Island Records; noteworthily, they signed him without even listening to it – a significant display of loyalty after his past professional struggles with The Train Robbers.
According to Bridges, Charley never allows others to take advantage of him, a trait that stems from his hands-on approach of working directly in the field without relying on machinery.
After securing a deal with a prominent record label, Crockett now has the opportunity to captivate new audiences with his lively music and flamboyant persona – that is, if Island Records delivers as promised, he jokes. However, there’s also a great deal of curiosity surrounding his vivid past, a subject that leaves him in a quandary. He admits that his life experiences have played a significant role in shaping him, but discussing certain aspects of them could potentially harm people close to him – particularly his brother and mother, who he claims are still deeply affected by the death of his sister 10 years ago due to a drug overdose.
He mentions, “She’ll never move past it,” referring to someone’s lingering feelings. However, he has relatives who have their own concerns about their past, which is causing them anxiety.

From Crockett’s perspective, as well as Jennings’, outlaw country isn’t defined by past troubles, but rather it embodies artistic liberty and creative autonomy. Additionally, Crockett is hesitant about being likened too closely to figures such as Willie and Waylon.
He remarks, ‘I can’t compete with those individuals.’ They were the ones who harvested cotton, understand what I’m saying? I grew up amidst cotton and sugarcane fields. However, no one was manually picking that stuff in the 80s. That era, they were simply tougher.
Eshak suggests that Crockett might find a way to make it big in country radio, but there could be obstacles and it’s uncertain if Charley will play his songs. He also mentions touring as an important factor for Crockett’s career. Additionally, Eshak sees potential for both Crockett and his wife Taylor Grace in film and television. In a nod to their relationship, Crockett wears a necklace with a silver pendant spelling out Taylor’s name at Sunset Sound.
“The two of them as a couple have this old-school kind of Hollywood glamour,” Eshak says.

Crockett, set to be the main act at the Houston Rodeo on March 17th, seems to have a stronger affinity for show business than some artists within the country music scene. He was intrigued by Timothée Chalamet’s speech during last month’s SAG Awards when Chalamet won the Best Actor award for his role as Bob Dylan in “A Complete Unknown.
What he expresses is this: “Right now, it seems like he doesn’t mind, but I admire that Timothée mentioned Brando, Viola Davis, and his aspiration to excel. It shows he values art and has a message to share, which is exactly what we require.
In front of Crockett, a whiteboard rests against the studio wall, filled with the titles of 28 songs he’s recording for his upcoming album – Vol. 2, which he plans as part of a Sagebrush Trilogy inspired by Ennio Morricone’s film series and Cormac McCarthy’s Border Trilogy. He confesses that he’s uncertain whether to include all 28 songs or trim down the playlist.
“There’s just so much good stuff,” he says. “I’m a late bloomer. I’ve got some catching up to do.”
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2025-03-13 13:31