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Charley Crockett on his long road to stardom and touring with his inspiration, Willie Nelson

One of many reasons Charley Crockett won the Americana Music Awards' Emerging Artist of the Year honor in 2021 is because his bluesy, countrified Americana music earned twice as many streams in 2021 than in the six prior years that his music has been available on platforms, combined. For most artists, experiencing this type of popularity after a 20-year career would be a cause for ecstatic celebration.

Instead, he's still unpacking music defined by his remarkable experiences and gained knowledge into a throwback, largely honky-tonk style. At the onset of a touring cycle that will take him through Halloween 2022, he's better than ever and poised for an enormous moment.

While speaking to The Tennessean, the San Benito, Texas native, recalls how his first meeting with mainstream acclaim informs why he laughs in the face of conventional thinking regarding success.

"A record industry executive tried to sign me early in my career. While we were talking in his office, he told me that an artist's career typically spanned three records in seven years," says Crockett.

He then makes a defiant statement:

"Man, I looked at that guy in the face and said, 'f*** that.'"

Charley Crockett's "Lil G.L. Presents: Jukebox Charley" is his 11th major album.
Charley Crockett's "Lil G.L. Presents: Jukebox Charley" is his 11th major album.

Crockett's having this conversation while waiting for a tailor to size him for pants for a custom stage suit. The reason? He's spending three months on the road in the summer of 2022 -- in various capacities -- with Willie Nelson, including a May 6 date opening for him at the FirstBank Amphitheater in Franklin, Tennessee. Plus, he's joining an all-star lineup including Nathaniel Rateliff & The Night Sweats, Jason Isbell and the 400 Unit, Allison Russell and Brittney Spencer at this summer's Outlaw Music Festival.

When Crockett is asked about how he feels about being one of few modern-era artists to be able to spend that much time around Nelson, he's stunned and immediately switches into a profoundly reflective mode. It's the only time on the call that the line is silent for more than five seconds.

Realize that his struggle with heart disease resulted in open-heart surgery in January 2019. Yet, three years later, he's closing in on stardom, and he's doing so with a 1993 Country Music Hall of Fame inductee who is an important trendsetter for his iconoclastic path.

Aside from Nelson, his path to success pays homage to a slew of his essential forebears.

On his April 22-released album "Lil' G.L. Presents: Jukebox Charley" (via Son of Davy/Thirty Tigers), he covers songs by other 60s and early 70s country favorites, including Johnny Paycheck, George Jones, Jerry Reed, and Tom T. Hall.

Furthermore, the name "Lil' G.L." has adorned two other albums in a trio of his albums since 2017. The name comes from G.L. Crockett — an early 60s' hit-making Mississippi R & B singer whose sound erred heavily into twang-boosted soul rhythms.

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Crockett's "Lil' G.L. Presents: Jukebox Charley" cover version of Nelson's 1963 single "Home Motel" offers the album's best overall material and the most significant insight into the rising star's mental state regarding the year to come.

"["Home Motel"] is my favorite track on the album. When I was a street musician, I was strictly seen as a blues and jazz artist -- nobody called my music country music. Willie released "Home Motel" in 1963, and it's jazzy and soulful," Crockett says. "It's also on his second album (1963's "Here's Willie Nelson"). He released 17 more albums in 12 years before hitting No. 1 in 1975 (with "Red Headed Stranger"). In that time, he developed as an artist -- singing a bittersweet, 'cabaret style' of country music -- to his full potential."

Charley Crockett accepts the award for Emerging Act of the Year during the Americana Music Association Awards ceremony at the Ryman Auditorium Wednesday, Sept. 22, 2021 in Nashville, Tenn.
Charley Crockett accepts the award for Emerging Act of the Year during the Americana Music Association Awards ceremony at the Ryman Auditorium Wednesday, Sept. 22, 2021 in Nashville, Tenn.

"We have to let artists make music and not slow down the record cycle. If you let artists -- and look at that era, there was Aretha Franklin, James Brown, Willie Nelson, so many -- who were allowed to grind it out in the studio and on the road to become masters of the craft before the industry said they were superstars," adds Crockett.

Continuing, he dives into why he's self-describing his new material as "Gulf and Western." It offers a clearer sense of his creative vision.

He's settled on the concept by intentionally alluding to the era between 1966-1974. During that time, Gulf and Western Industries (formerly Paramount, currently Viacom) distributed both iconic soul labels Stax Records and country imprint Dot Records.

In this context, it's a perfect descriptor for his journey from busking streets to headlining clubs nationwide, with a sound fusing into a singular style that encapsulates timeless excellence in blues, R&B, soul, Cajun, reggae and western swing.

It may be the best way to encapsulate Crockett's life -- one that's seen him play in every conceivable place possible from North Africa to North Dallas, Texas -- in a way that doesn't sound as unbelievable as it seems.

"When I was 'discovered' in New York City, I was busking on the subway with a vocal harmonizing group from St. Lucia singing Toots and the Maytals and Bob Marley," Crockett says relating another unbelievable but true story. "While they were singing that, I played my classic country songs," Crockett recalls. "They were the ones who pointed out to me how much their music and 60s honky-tonk country had in common. There's not much difference between George Jones and Studio One (noting an influential 60s and 70s era reggae label)."

His diverse musical knowledge and dogged determination are what he lists as guiding his success.

"Playing these sounds, the way I know them blends them so close together," says Crockett. "I've been grinding for years, and I think I'm still getting better at my craft."

Charley Crockett performs Are We Lonesome Yet during the Americana Music Association Awards ceremony at the Ryman Auditorium Wednesday, Sept. 22, 2021 in Nashville, Tenn.
Charley Crockett performs Are We Lonesome Yet during the Americana Music Association Awards ceremony at the Ryman Auditorium Wednesday, Sept. 22, 2021 in Nashville, Tenn.

Longer into the 60-minute conversation, the artist who experienced his most tremendous success with his 2021 album "Music City USA" shares a fascinating thought: He's keenly aware that he's 11 albums into an impressive run that mirrors Nelson's career.

Notably, Nelson took nearly 20 albums to finally reach No. 1 on Billboard's Country Sales charts with 1975's double-platinum selling "Red Headed Stranger." If math holds true, Crockett will claim similar success in the next half-decade.

Crockett has an unshaken, resolute tone in his voice as he ponders this reality out loud.

"Imagine if my first five records are all I ever released? Instead, I'm blessed to have over ten albums out because I refused to be exploited by the music business and gone in under a decade," Crockett says. "In the past, artists were allowed to grow and survive that."

Famously, Charley Crockett is very aware of his style and aesthetic, from his song selection to his outfit choices. The appeal of both has yielded a career that has, after nearly 20 years, set him upon a path that has finally aligned him with his destiny.

When asked about what his future entails, Crockett sums up his final steps to superstardom with well-worn wisdom.

"Don't ask a man his shoe size if you haven't paid the dues to fit his shoes."

This article originally appeared on Nashville Tennessean: Charley Crockett on his road to stardom and touring with Willie Nelson