How Charley Crockett Makes New Music Sound Old (and Old Music Sound Brand New)

Charley Crockett knows his story seems far-fetched.

“People always tell me, ‘Man, you didn’t ride trains — that’s not possible, no one does that anymore,'” he says, sitting at his tour bus’s small table. Crockett is clearly frustrated – the fact that he’s traded train cars for tour buses and street corners for venerable stages that he shares with even more venerable artists makes his improbable origin story even less likely. “I’m like, ‘You don’t know what the f*** you’re talking about. You have no clue.’ It’s easier than ever to get on a f****** train, and there’s a ton of kids doing it. I never intended to do that, I fell into it — and I couldn’t believe it. I was so shocked at the amount of disillusioned kids coming from poverty in America resorting to riding trains.”

It’s a scorching July day that’s even more scorching in the vast South Dallas parking lot where Crockett’s tour bus has stopped for the afternoon a few hours before San Benito, Texas native and his band take the stage for their fifth set with Willie Nelson’s traveling Outlaw Festival. Many of the Blue Drifters, as they’re called, have been with Crockett since not long after he “came in from playing exclusively outside,” as he puts it, and have been called on to corroborate his unlikely origins — which they do, willingly.

Crockett’s past does seem larger-than-life — like fodder for the tall tales and gossip of some frontier town. It’s not just the years of domestic and international travel as a transient, busking to get enough money for food and little else, that seem like they could be exaggerated. There’s the fact that Crockett claims relation to folk hero Davy Crockett, who inspired the name of the independent label upon which he releases all his music, Son of Davy. He shares his border hometown, San Benito, with pioneering Texas genre-bender Freddy Fender. His scrapes with the law could’ve turned out worse: When he was arrested for possessing a substantial amount of marijuana, he sent the judge his music and begged him not to hinder his career — and it worked. Oh, and when a congenital heart condition necessitated open heart surgery in early 2019, surgeons replaced one valve of his heart with a cow’s. He is literally a cowboy.

“All those things will show themselves as years go by, that everything I ever said I am is true and then some,” the 38-year-old says. As Crockett releases The Man From Waco, his 11th album in seven years, he’s reaching towards his broadest audience yet the only way he knows how: by digging even deeper into America and its music and, specifically, the idiosyncratic way he’s known and seen both. He keeps telling those unbelievable stories because believability is his stock-in-trade; not everyone can pull from as wide a range of sources and eras and influences as he does without it feeling like costume or caricature. That wild journey — so foreign to the vast majority of the contemporary music industry — made him, as he argues, and made him into one of the most potent and convincing artists working in the country and Americana scenes today.

Learning music as a persistent and curious busker meant that Crockett’s first text was the broadest possible version of the American Songbook, one that he took in almost exclusively aurally. As a result, it is not only the songs he sings that tie him to another time but the pragmatic, casual, offline way he adopted them — hearing, learning and performing those songs without much context, a friendly audience or the pomp of a traditional venue.

“The greatest gift of my story of a broken road — a lot of fortune, a lot of misery, a lot of suffering, a lot of happiness — it’s all tied together just by the satisfaction of knowing these folk songs,” Crockett says. It’s perhaps no surprise that a man whose life has had such poetic contours appreciates them so deeply in song; his reverence is so deep that he’s released four covers-only albums, all of which he presents under the moniker Lil’ G.L. — a tribute to G.L. Crockett, a country-blues singer to whom Crockett is not related.

But there is not even a little stylistic difference between the covers albums and the ones that include original songs; instead, they are presented as he learned them, a glorious all-American mish-mash of genres and eras and styles. Like his audience, he often hadn’t known who wrote those songs or who originally performed them when he first heard them.

“I learned ‘My Bucket’s Got A Hole In It’ off a Cajun teenager named Sal in New Orleans,” Crockett recalls. “I learned it and was doing it, and then someone told me it was a Hank Williams song. That happened with everything. S***, I was doing Tom Waits songs that I thought were mid-19th-century spirituals. That happened with him twice; that happened with Dylan 100 times.”

Dylan, and Willie, and Dolly, and Lightnin’ Hopkins, and Lavelle White are just a few of the names Crockett will bring up over and over again when explaining his own music. Only by following their paths and learning America’s music from the ground up — forsaking anxiety about originality and authenticity along the way — was Crockett able to find both his sound and his voice as a songwriter. His prolific catalog can be divided into songs he wrote that sound timeless enough it seems like they’ve always existed, and songs he didn’t write (that depending on your age and/or music nerdom you may or may not be familiar with) that he makes sound so natural and fresh it’s hard to imagine them any other way.

To explain how he’s able to write songs that blend so seamlessly with those of his inspirations, he references Bob Dylan’s speech from the 2015 Grammys, when Dylan was named the MusiCares Person Of The Year: “He was like, ‘If you sang the folk songs that I sang as many times as I did, you’d be writing these songs too,'” he says. “That’s not even complicated, and I’m not very smart. I just sang ‘March Wind’s Gonna Blow My Blues All Away‘ a million times. I sang ‘Bei Mir Bist Du Schoen‘ a million times. I know music the way that I do because I learned how to live and play music on a street corner. I’ve not only done that, but I’ve done it so many more hours than anyone around believes that I did.”

Bob Dylan appears as a co-writer on The Man From Waco. “Tom Turkey” is Crockett’s completed version of a fragment from Dylan’s Pecos Blues collection, outtakes from his soundtrack for the 1973 Western Pat Garrett And Billy The Kid — the same process, Crockett notes, by which Old Crow Medicine Show wrote the still-inescapable “Wagon Wheel.”

That’s the closest this album gets to a cover, though. The Man From Waco is a collection of originals that outline a fictional Western epic with a title inspired by one of Crockett’s real-life friends and heroes, the late Texas singer-songwriter James “Slim” Hand, who was born in Waco, Texas and passed there in 2020. Crocket had already recorded a tribute album of Hand’s songs, 10 For Slim, so rather than exploring his musical legacy or biography, The Man From Waco uses the idea of him as a jumping off point. Crockett’s own take on Western mythology is inspired in part by Jim Jarmusch’s 1995 revisionist Western Dead Man: On the album, a man accidentally kills the woman he loves in a jealous rage, an act that figuratively and then literally kills him.”He can’t outrun what he did,” says Crockett.

To tell that story, Crockett deploys much of his aesthetic arsenal. Crockett turned to fellow Texas singer-songwriter Bruce Robison to produce the release, cutting live to two-inch tape with limited overdubs. His studio sound is his live sound, and vice versa, in part — again — because of the portable, minimalist way Crockett refined his skills in the first place. “Any mistakes, if the vibe was there and it didn’t take away from it, they stayed in,” he says. “Time Of The Cottonwood Trees” is a tragically pretty, deceptively simple folk ballad; the title track is all theatrical Western bravado through a ’70s haze; “I’m Just A Clown,” the first single, has a classic R&B groove. Crockett recorded with his well-honed touring band for the first time, seeking to recapture the easy energy of his first release, A Stolen Jewel, which was recorded while he was working on a farm in Mendocino County. He even re-recorded one of that album’s highlights, “Trinity River” — an ode to the Dallas-Fort Worth waters that shaped him after his family moved there when he was a teenager, and where he found creative inspiration as an adult busking and eventually gigging in Dallas’ historic musical core, Deep Ellum.

Crockett’s musical journey led him to a kind of aesthetic continuity that has been framed as “gulf and western,” a Jimmy Buffett-inspired term that may not be all that descriptive, but that Crockett embraces precisely because of its geographic rootedness. The Son of Davy logo is overlapping outlines of Texas and Louisiana; the western Gulf coast and its environs (namely Dallas, Fort Worth and Austin) are home to the sounds Crockett always finds himself returning to. He loves to recount the fact that when he was young and learning guitar, he thought he’d invented new chords — until he learned a T-Bone Walker song while living in New York and found that Walker had used the exact same ones almost a century prior, when he was helping innovate the blues on the corners of Deep Ellum.

“I could run away from my history, from Texas; I can try to forget the things in my past that are a burden to me or are sucking me dry,” says Crockett. “But there’s the obviousness that region and place affects who you are, all the way. I didn’t invent the chords, I was playing the sound like T-Bone because I was walking a road like that, in my time. That’s when I started to develop a true pride and identity that I did not have previously: I found power and strength and confidence in standing on a street corner and started realizing that I could support myself hand to mouth, travel the way that I wanted to, and that I was better off.”

Crockett has always released his albums independently with distribution by Thirty Tigers, a move that allows him to keep creative control and continue to refine the burnished, warm, genre-agnostic tack that is so distinctively his. As he often puts it, he pulls songs and sounds from the foundations of American music and “washes them anew” — a beautiful image, like someone meticulously taking apart old songs, cleaning all their nooks and crannies with a soft toothbrush, and then putting them back together.

“I think I’m a folk singer. It’s blues, it’s country, it’s jazz, it’s gospel, but all of that is folk music,” says Crockett. “Especially now, I’m just reminding myself that it’s folk music.”

As a result, his work has an undeniable vintage hue — one that some might write off at first glance as the dull mimicry of just another retrophiliac. But especially set beside his inspirations, the modernity and wit of Crockett’s new-old sound become obvious. Clean but not sanitized, analog but not alienating, what Crockett has found in digesting all these different traditions and digging deep in the fertile Southeast Texas soil is style, something he can keep tapping and honing for as long as he’s playing.

Crockett might release records at a dizzying clip, but the place where he’s undoubtedly converted the greatest number of fans is onstage, maintaining a relentless and unexpectedly diverse touring schedule with admirable energy, charisma and polish. Or as he puts it, gesturing to his tour bus, “Well, as you can see, I never got out of the transient lifestyle.”

Just in North Texas, I’ve seen him at music festivals, theaters and state fairs (“Is this country music?” one woman near me inquired seeing the crowd that had gathered before Crockett’s set at the State Fair of Texas last fall. The reply was unequivocal: “Oh yes.”) — and that’s without considering the increasingly large venues on the coasts and abroad that he’s filling now that he shares a booking agent with Willie Nelson.

This fall, he’ll play at New York’s venerable Webster Hall, as well as two shows apiece in Seattle and Los Angeles at theaters that hold more than a thousand people — making it impossible to ignore how unusual it is that he can now draw those kinds of audiences in coastal hubs as easily as he can fill venerable Texas venues like John T. Floore’s and Gruene Hall. At a PBR-sponsored (that’s the rodeo, not the beer) headlining show at Fort Worth’s Will Rogers Auditorium (2,856 seats) where I saw him back in May, the beer line was filled with horse talk, and I occasionally caught the faintest whiff of manure stuck on some square-toed cowboy boot.

“I don’t sing folk music for a conservative crowd, and I don’t speak my stories through song for a progressive crowd,” he says. “I speak it because this s*** is true to me.”

Crockett doesn’t take the political implications of his music lightly — his first album, A Stolen Jewel, is named for a song he wrote about colonialism, and the diverse covers he chooses serve as a rebuke of those who are proactively trying to keep country music white and conservative. But not compromising his own values while trying to make music that reaches beyond political and cultural divides is still, in his words, a “tightrope act.”

“That’s one of the great challenges of America,” he told me in a 2021 interview. “You just have to kind of decide at some point: Do I want to speak only to an audience that thinks like me, or do I want to speak to a wider audience? That doesn’t mean I’m going to censor myself. But I’m not going to stop anybody from listening to me, because I actually want to change people’s minds. Not just about racial issues or gender issues, but I want to change people’s viewpoint of the whole world.” After all, as he correctly assesses, one of the reasons “Welcome To Hard Times” (released during the summer of 2020) became his national breakout is that everyone who hears it — no matter their circumstances — thinks it’s even more true for them than it is for anyone else.

Crockett’s heritage adds another element of complexity to his ability to traverse a slew of different audiences. “A lot of people see me as white, a lot of people see me as Black,” Crockett says. “A lot of people see me as somebody safely in-between, which just kind of makes you like a weird outcast. That’s just been a big part of who I am, being in-between. I’ve got country boys in West Texas that don’t see me as anything but a cowboy like them. Then there are urban people looking at me as like, representing diversity in country music. With the last record, and them wanting to push all this stuff with race, the truth is that I’m mostly white but I’m just different enough that country people are really weird about it.” Or as he puts it more candidly, they’re “wondering what Steph Curry is doing in a cowboy hat.”

Regardless of where they happen, people at Crockett’s shows wind up rapt. Years of survival by compelling apathetic bystanders to have fun helped Crockett cultivate not just his sound, but his showmanship — he pulls out 60-year-old dance moves that seem to have otherwise gone extinct, packs sets full of songs spanning his vast catalog with next to no pauses for awkward stage banter, keeps the same polished band that he’s now had for years. It’s good-timing music, and he makes sure audiences have one.

Earning fans everywhere he goes comes with its own tradeoffs, and as Crockett’s star rises they become more obvious. The last song on The Man From Waco is called “Name on a Billboard“: “Hey look my name is up in lights/Somehow I still don’t feel right,” Crockett sings. Not coincidentally, Crockett bought billboards to promote Welcome To Hard Times when they were cheap due to the COVID-19 pandemic. It became his most successful album to that point, setting him on the road to earning the Americana Award for Emerging Artist of the Year in 2021; now, the stakes are raised despite the fact that, as he’s sung, “the dice are loaded and everything’s fixed.” It chafes, a little, all the pomp and ceremony.

“Somebody like Billy the Kid, he was dead by the time he was 21,” says Crockett. “There’s physical death, there’s spiritual death … there’s all these things that can happen when too many people are looking at you. That idea is running through The Man From Waco.”

Crockett has his own definition of success: to be able to “sing anything and sound believable.” “I believe that everybody has that in their essence, it’s just not very many people go down that road and stay on that road,” he adds. “There’s a lot of roads, and it’s not the only one and it ain’t the only worthwhile one — not even close. I can tell you a lot of times, it doesn’t feel worthwhile. It seems like you’re lost and you’re not coming back.”

Whether he’ll be believed as a man and as a musician as he continues to ascend is an open question. So for now, he’s doing his best to stay grounded in the things that got him this far.

“I was in Rock Island, Illinois, just walking down the railroad track in the heat of the day because I felt stuck in this tin can,” he says, again gesturing to the tour bus. “I was watching a freight train coming down the line real slow, and the last car just stopped right in front of me. I was like, ‘There you go.'” There were people, just like a younger Crockett, inside the freight car.

“I could have just got on it,” he says. “In some ways, I never felt more like disappearing back into that than I did the other morning.”

But this time, he let the train go by. The songs are what he’s searching for now, and they’re taking him where he wants to go.