Charley Crockett Looks Back — And Moves Forward — With Covers Album ‘Jukebox Charley’: ‘I Wanted to Not Do the Obvious Stuff’

Since the start of the pandemic in 2020, Charley Crockett just might be among the most prolific recording artists in any musical genre.

His upcoming album Lil’ G.L. Presents: Jukebox Charley, out Friday (April 22) via Son of Davy/Thirty Tigers, marks his fifth full-length studio album in just over two years. It’s also the latest in his G.L. series of tribute albums (last year’s Lil’ G.L. project paid tribute to James “Slim” Hand), this time delving deep into a goldmine of obscure country gems — and applying his amalgam of country, blues, Cajun and R&B to some of the lesser-known entries from Willie Nelson, Tom T. Hall, Red Sovine, George Jones, and more.

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The tracklist includes “Between My House and Town,” a Sanger D. “Whitey” Shafer-penned track Jones recorded on his 1968 album If My Heart Had Windows, and “Make Way for a Better Man,” penned by Cy Coben and recorded by Nelson on his 1967 album Make Way for Willie Nelson. The album’s title track is a Johnny Paycheck cut, while the lead single is a rendition of “I Feel For You,” from Jerry Reed’s 1967 debut album The Unbelievable Guitar & Voice of Jerry Reed.

“I have this running list on YouTube of about 900 songs, and a couple thousand old country records,” Crockett tells Billboard of his song selection process. “There are a lot of recordings on those LPs that are really hard to find any other place. All these country, blues and R&B artists, they were recording so much. If you signed a deal in the 1950s or 1960s, you were doing a few releases a year. When I get ready to make these kinds of albums, I’m always making lists of songs. I must have listed out 40 songs for this album and I wanted to not do the obvious stuff, like Merle Haggard’s ‘Swinging Doors.’”

Crockett says one of the songs on the album, “Lonely in Person,” penned by Tom T. Hall, was so obscure he didn’t even know Hall was the writer when he first heard it.

“My girlfriend Taylor Grace found it in a very obscure record compilation out of Louisiana called Rice Records. It was Buddy Meredith singing it. I love a song that shows what a traveling entertainer is experiencing — the description of the happy people listening to the man singing songs and loving life, yet they would never think it is lonely up there,” Crockett says. “When we went to find out the publishing on the song, you have to go find the pictures of those old 45s to get an idea of who wrote it and do that detective work. Once we saw the 45, it said Tom Hall—it didn’t say Tom T. Hall. When they went to the publishers, they said it was a Tom T. Hall song.”

For Crockett, the covers albums are about more than just tipping a hat to classic artists — it’s a reminder that the work of an artist takes time to mature and build, something often missing in the streaming era.

“I think there’s a lot of amnesia, and people think they are reinventing the wheel, when they’re not looking back. This business makes it difficult for an artist to ever really bloom. We all know Aretha Franklin was a household name and d–n well should be. But she recorded nine albums of pop songs in New York City before Jerry Wexler took her to Muscle Shoals. Willie did not break through until his 17th or 18th album with [1975’s] Red Headed Stranger, and Johnny Cash had several albums out before I Walk the Line.”

Since releasing his first album, 2015’s A Stolen Jewel, Crockett has made a point of alternating projects of original music with batches of covers albums — all drawing from the earlier eras of country and blues music he learned to play while working as a street musician and then working smaller clubs.

Along the way, Crockett has retained a staunchly independent vision, aligning with hit artist/writer Bruce Robison at The Next Waltz for management, Angela Backstrom handling Americana radio, and teaming his own Son of Davy label with Thirty Tigers (“I’ve been making records all along the way and I own all of it, every record,” Crockett says).

“Independence has been key for him,” Robison tells Billboard. “There used to be 10 different industries — label, merchandising, publishing, radio — it felt like hundreds of people. And now, you’re doing all of that yourself, every bit of it. And Charley’s overseeing all of that — the graphics, artwork, he’s so involved in every aspect.”

That’s in part due to nearly getting caught up in what Crockett calls “the pop machine” about a decade ago. “I used to perform in subway cars in New York City for two years, and two really big people in the industry, a husband and wife, they plugged us into the pop machine and I saw how it all worked,” Crockett says. “I was only around it for about eight weeks before I bailed, but it was enough time to see the pop machine, the co-writers, the electronic pop dance beat that was popular at the time, 10 or so years ago. They build you up, lock your publishing down, the focus groups…

“The crazy thing is a lot of the big labels are still presenting me with the same package they did 10 years ago,” he continues. “The difference is, 10 years ago, I was a desperate street person with no money. Now I have a pretty d–n big grassroots following. So when people come around and offer me an entry-level, bulls—t a— deal designed for someone who thinks the only way is American Idol, I can’t help but smile.”

Instead, Crockett and his team have focused on putting out music and touring, and the work has paid off. Last year, after the release of his album Music City U.S.A., he was named emerging act of the year at the Americana Music Honors and Awards ceremony. Then, in December 2021, he made his only partnership with a major company thus far, signing with CAA agent Lee Goforth for booking — though Crockett says it was a hard decision.

“When they first approached me, I was fiercely resistant to dealing with somebody that comes with that big name, the Goliaths,” Crockett says. “I was avoiding them, but then Bruce said, ‘You need to see all the options that are out there, so you can make the best decisions for you and your family.’ I was overworking some markets. I saw it one night in a venue in Oklahoma. I was filling in the holes for people. They were bringing me back every quarter and didn’t have to spend money to promote me. I thought, ‘If you keep doing this, your ticket sales are gonna level off and you might never get it back.’ I had to make some decisions.”

“We saw him as a career artist, someone who will be doing this for the next 40 or 50 years, similar to some of the people he looks up to, like Willie Nelson,” Goforth says. “For us it was just about strategizing and picking the right moments to play certain markets. He’s really strong in Texas and the Southeast, but also in Colorado and the West Coast — Denver, Los Angeles and San Francisco are also key markets.”

This year, in addition to headlining his Jukebox Charley spring tour, Crockett is booked as an opener for Willie Nelson’s Outlaw Music Festival this summer (CAA also books Nelson). He also performed alongside Nelson at the Luck Reunion festival in March.

With Crockett’s new alignment with CAA, Goforth says licensing Crockett’s music for film and television could be in the works, while Goforth also says it’s possible that Crockett could possibly follow in his legendary fellow Texan’s footsteps and launch his own festival at some point.

“We’ve had a lot of talk already about what that could look like for him,” Goforth says. “His ties and roots in Texas and the fans he has there, it will be a lot of planning and at the right time we feel like that will be something interesting for him and something he wants to do.”

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