Charley Crockett on Signing With Island, Celebrating a Decade of Genre-Fusing Music With ‘Lonesome Drifter’: ‘I Wanted to Maintain Ownership’

On his new album, Lonesome Drifter, out Friday (March 14), Charley Crockett traverses new career territory while simultaneously nodding to his roots.

In the past near-decade, the prolific Crockett has released 13 albums, each on his independent label Son of Davy and nine of them in conjunction with Thirty Tigers. For Lonesome Drifter, which he recorded over a 10-day span at Los Angeles’ Sunset Sounds Studio, the fiercely independent-minded Crockett made a major career shift, signing with UMG’s Island Records.

“The last few years, all the majors started calling,” he tells Billboard, noting that he nearly signed with Columbia Records at one point, given that it had been at points the home of two of his musical icons, Bob Dylan and Johnny Cash.

But he says Island Records understood what he was seeking in a label partner. “It’s been a process in the past few years of seeing labels realize that if you don’t do a licensing deal with my company, or my friends’ companies, we’re just not going to do [the deal],” Crockett says. “Island agreed to all the things I was looking for, which was I wanted to maintain ownership and have creative control.”

Crockett has spent years building his reputation as a musician’s musician, an artist fueled by creativity and fashioning songs that mirror the lives and stories he sees around him, while also nodding to a deep understanding of the ties and history connecting country, folk, blues and more. In making the choice to sign with Island, he also wanted to make sure he wasn’t erecting creative boundaries in his career.

“Island wasn’t like, ‘Hey let’s take this thing to Nashville and focus on Nashville radio,’” he says. “I didn’t want to be stuck in that because I’ve always felt the thing in Nashville was ‘He’s too country,’ or ‘He’s not country enough.’ No matter who I was dealing with in Nashville, that was always the viewpoint. Not to be controversial here, but I’ve been around a long time and seen a lot of back rooms in Nashville and the money’s still coming from New York — just like Willie [Nelson] and Waylon [Jennings] figured out.

“[Island Records co-chairman/co-CEO] Justin Eshak, he did the whole deal, got all the paperwork, we signed the deal and everything, and they had never heard the [Lonesome Drifter] record,” Crockett continues. “It was like, ‘Look at these records we put out before it. If you like those records, then you’ve got nothing to worry about.’”

To commemorate the release of the new album, and the new label deal, Crockett has been giving away 100,000 copies of a four-song CD sampler at locations around the United States, including at 200 record stores across the country, at SXSW and the Houston and Austin Rodeos, and at Luck Reunion and the Luck Record Club. The choice brings him full circle — as a decade ago, he handed out 5,000 free copies of his self-released 2015 A Stolen Jewel.

“It was my wife’s idea. She’s a lot smarter than I am,” Crockett says, his grin audible as he gives credit for the Lonesome Drifter giveaway to his wife Taylor. “She mentioned it had been 10 years, and was like, ‘Let’s remind them how you did it. Let’s do 100,000 instead of 5,000.’ We went to the Universal building and Taylor threw that idea out in front of Island and they said, ‘It sounds like a hip-hop model,’ and when I say hip-hop, I mean DIY. And they weren’t scared of it.”

Crockett co-produced Lonesome Drifter with singer-songwriter-producer Shooter Jennings, son of Waylon Jennings and Jessi Colter. One of the songs released from the album, “Game I Can’t Win,” inspired by the work of Woody Guthrie, looks at greed from an underdog’s perspective. He takes a shot at Music City on the line, “Them boys in Nashville, they don’t mess around/ Better watch ’em when your deal goes down.”

“The phrase ‘I always love a game I can’t win’ came into my head, because it’s true,” he says. “The thing about America is: No matter what background people are coming from, people feel that it is rigged, that the cards are marked in advance. I think people feel that. When I think about parlor games, think about casinos — we know when we walk into a casino that the game is set up for the house to win, but even with all the odds stacked against you in America, you can win as hard as it is, as rigged as it is, as much favor for a favor [that] there is. For me personally, being from South Texas, I feel that you can win, and I think that’s at the heart of all Americans, that’s kind who we are.

“’I Can’t Win,’ a lot of it is two songs jammed together,” he continues. “When I put them in front of Shooter, he made me see how Willie and Waylon and them were doing. Willie was really good at taking what looked like two totally different sketches and making them one. Shooter helped give some context to that for me to finish some songs.”

“Easy Money” was inspired in part by the 1969 movie Midnight Cowboy, taking in the story arc of a Texan who seeks his fortunes in New York. Crockett began writing a freehand poem as he watched the movie. “I also remembered this person, a friend’s sister, who started dancing at a gentlemen’s club, Silver City in West Dallas. It all hit me, this idea of ‘easy money,’ but if you’re poor, there’s no such thing as easy money.”

The album closes with a cover of George Strait’s 1982 hit “Amarillo By Morning,” written by Terry Stafford and Paul Fraser in 1973. Before Strait’s version became prominent, Stafford released a version of the song in 1973, while Chris LeDoux recorded it as part of his 1975 album Life as a Rodeo Man.

“I’m a huge Terry Stafford fan,” Crockett says. “I knew all of George Strait’s songs when I was a kid, and ‘Amarillo by Morning’ was always a favorite. I thought, ‘I’m going to recut this. It’s 40 years old.’ But when I told Shooter about it in, I second-guessed myself and was like, ‘Never mind. They are going to judge the s–t out of me. George Strait owns that song.’ But Shooter’s heart was set on it and we did cut it. When I sing [songs like his own] ‘$10 Cowboy,’ it’s like, ‘I’m not George Strait. I’m not a rodeo guy.’ [But the “Amarillo by Morning” lyric] ‘I’m not rich, but Lord, I’m free,’ that’s how I live my life. I wake up every morning and I’ve got more responsibility than I ever did, but I know I still have that freedom of choice.”

Crockett was born in San Benito, close to the Texas-Mexico border, before his family moved to the Dallas-Fort Worth area (he also spent summers with family in New Orleans). He grew up soaking in an array of music, including Jennings, Nelson, Curtis Mayfield and ZZ Top, in addition to folk-troubadours like Dylan and Guthrie.

“I went to New York City because of this idolizing of what I heard or read about that scene in NYC that Bob took that folky thing in the village and took it to the world,” Crockett says. “Looking back now, there was a lot of darkness with that, and I couldn’t live there. I did learn that New York is the empire, the heart of the empire and if you try to get on top of the empire and stay on top, it can destroy you. That concrete jungle is so big. We got offered so many record deals, management deals, all that kind of s–t on those subway cars…one positive thing that’s changed about the business [is] there’s a lot of artists out there and they’re just amplifying what they are doing when they discover ‘em.”

He continued busking his way across the country, playing on the streets of California, Colorado and Paris, France, before making his way back to Texas. Along the way, he offered listeners CDs out of his guitar case, on the advice of other, more seasoned transient performers.

“If I was staying with someone, I would record the songs that I knew real quick with the built-in microphone on their laptop and then burn those onto CDs,” he says. “I’d wrap those up in colorful ads and magazines and sell them for $5,” he says, recalling that “the amount of money people threw in my case increased overnight — I realized I looked more legitimate.”

He had handed one of those CDs to Turnpike Troubadours lead singer Evan Felker outside of Gruene Hall in New Braunfels, Texas. The CD made its way into the hands of Turnpike’s booking agent Red 11 Music, Jon Folk (Red 11 Music was acquired by WME in 2023. Crockett is represented worldwide for booking by CAA). The Folk connection led to Crockett previously aligning with Thirty Tigers.

“The good thing about the way I did it, is I made a lot of records really cheaply with [Thirty Tigers’ co-founder/president David] Macias over the course of those seven, eight years, that allowed me to develop my sound,” Crockett says.

As his sound solidified, his prominence has grown. Crockett has continued putting in the time in both the studio and the road, playing over 100 shows over the past year. He’s been nominated for numerous Americana Honors & Awards and was named emerging artist of the year in 2021. Last year, he earned his first Grammy nomination, as his 2024 $10 Cowboy release was nominated for best Americana album.

His Island Records debut Lonesome Drifter comes not quite eight months after $10 Cowboy Chapter II: Visions of Dallas. The frequent releases Crockett has become known for serve as needed deadlines to help drive the singer-songwriter’s creativity.

“One of the reasons I record so often is because I’m really good at starting songs, but I’m not always great at finishing them, if I don’t have pressure,” Crockett says. “I need a bunch of pressure and not a lot of time, so booking studio sessions is how I finish songs.”

And there are more on the way — Crockett says Lonesome Drifter is the first in a trilogy of projects, noting, “I just got the second one done, and I’ve got the theme and sketch of the third one done.”

Related Images: