You'll be hard pressed to find a musician that works harder than Charley Crockett. Prior to his career as a country crooner, the Texas native has done everything from working for cattle ranchers to cultivating marijuana. And since his first official release in 2015, Crockett has become one of the most prolific artists in music — and his work ethic is at the heart of Dollar A Day.
Out Aug. 8, the album not only marks his 16th in a 10-year span, but also his second in 2025 following March's Lonesome Drifter. The 15-song project sees Crockett detail his struggle to find success in the music business and the chip on his shoulder it's left. Whether it's bangers like "Dollar A Day" and "Tennessee Quick Cash" that touch on making art in poverty, or others about his blue-collar work ethic ("I Stay Ready") and staying away from shady suits ("Cruficied Son"), Crockett has a way of telling it like it is with a resonant twang that few others can match.
The hard-fought narrative is a continuation of themes he's explored on previous releases; he ruminated on not seeing a future in music on 2018's "How Long Will I Last," having the cards stacked against him on 2020's "Welcome To Hard Times," and shady record deals on Lonesome Drifter's "Game I Can't Win." But on Dollar A Day, he's more steadfast than ever in calling his shots after being a pawn in other's games for so long. He alludes to this directly on "Santa Fe Ring" as he pleads, "I've tried to take advice/ I've been a gambler all my life/ Getting shot from behind/ That aint no way to die."
The album is the second installment in what Crockett calls The Sagebrush Trilogy, which began with Lonesome Drifter. Both albums were a collaboration with Shooter Jennings and follow the theme of classic Westerns, with a mysterious, cloaked stranger swooping in to save the town from everything from sweet talking swindlers to gun-wielding gang busters. The Sagebrush recordings are also Crockett's first on Island Records, who he signed with in January after the label offered him full creative and release control over his work, something he was adamant about in negotiations but few people were willing to offer.
Crockett's stubbornness and unabashed desire to make music his way has drawn comparisons to modern day contemporaries like Tyler Childers and Sturgill Simpson. However, while each's mindset is similar, Crockett is quick to point out one key difference in their paths.
"For each of them it was their first or second record that really popped off — I'm on number 16 and people are still just finding out about me," Crockett emphasizes. "It's been very difficult for me to stay in the game this long being underground the way that I have."
Yet, his slow burn to success is a reminder of the beauty that can come from patience, grit and staying true to yourself no matter what others think. That, and there's never too much of a good thing, especially when it comes to compilations from Charley Crockett.
Below, in his own words, the GRAMMY nominee details how his latest set honors his unconventional rise to country music stardom, the hypocrisy of the music business, and making art on his own terms — all with his signature swagger.
It has been 10 years since I put out the first record — if you can call it that. I had a lot of recordings prior to then that for modern standards would be considered more underground or field recordings than anything else. My most popular record over that time from a streaming standpoint has been 2016's In The Night. I had a manager on a handshake deal that I found playing around bars in Texas a decade ago pitch that record really hard, but nobody would pick it up. I tell you that because there was simply no place for me in the business, even when I first got signed, since that was really just a favor for my then-agent when I was working the old Red Dirt circuit.
A couple years later, I put a record out called Lonesome As A Shadow that most of my label advance paid for, and the rest I blew on a publicist that didn't know how to market me at all. Honestly, if I'd left it up to them that would've been the end of it. "Well, this guy's confusing. He doesn't fit a clear classification. We tried. Time to move on." That's how so many of these records were made, because if I did it their way I'd be done before I even got started.
The only reason we're here talking now is because I went back to making records with the least amount of tools. Take A Stolen Jewel, for example, which I put out in 2015 and paid for mostly with a couple pounds of weed I'd been given by a ganja farmer I was working for as compensation for extra work I'd done in cultivating the harvest. I then gave that to another farmhand who was also a musician and now plays bass for me, Kyle Madrigal, and he paid everyone out of that, which basically equated to making the record for $5,000.
After Lonesome As A Shadow came out and they saw it as a cheap investment that didn't work out, I went back to doing that. The reason that's important is that Waylon Jennings and Willie Nelson were really struggling those first several years that they were on RCA. But the difference between the business back then in Nashville and the model now was even if Willie and Waylon weren't really profitable, there was a path of development and a philosophy that you made a couple of records a year on the Nashville assembly line to get your name out. Nowadays they just throw cash at a young signing and hope that the team around them goes viral, and if it doesn't they move on — which is never the way I've done it.
I always say there's only two business models — there's the suit's model and there's the Willie Nelson model. The latter has been seen very few times, but what has changed since the pandemic with a few artists, including myself, is proving that when you have an audience that truly accepts you, they take you as a whole. I think a lot about how that model has changed, even if it's just in relation to how I deal with Universal Music.
There are some artists who are proving that you could damn near put out music whenever you want. And so what I think changed for me is I was told, even in the Americana world, where they're behaving exactly like the majors used to, with just a much lower ceiling — that if you put out music more often than every 24 months, you're going to flood the block box and lose your audience's interest. I think I'm an example that that's totally wrong.
[When] Anthony Ferrell wrote ["I Stay Ready"], he was really looking hard at what I've overcome in the business from where he's standing. It's one of those things where it's really hard and a pretty raw deal accepting the reality of the music business in America — they're either making you or you're making yourself. Oftentimes you're in their business, but they're not in the Charley Crockett business.
My experience the entire way has been people plugging me into a bigger scheme that they've got going on, and the success of that scheme is often based on me not realizing their bigger business model. It's like a management company bringing you in for the main reason of running revenue models on what you'll be worth to them over the course of five years and applying that revenue to how they're going to expand their business or attract other artists. But I've found that as soon as an artist starts to play the same game on them that they're running around crying foul and bloody murder even though it's alright for them to hustle you all day.
My wife Taylor came up with the idea [for "Crucified Son"], and we started writing it when I was filling in for Bob Dylan on [Willie Nelson's] Outlaw Tour because he couldn't make a show in New Hampshire. As if anybody could possibly fill in for Dylan! But we got to thinking about the public — or even Jesus Christ himself — said he pays for everyone's sins, and the same can be said within the music business.
Shooter Jennings is simply a different man than Waylon Jennings, but there's a percentage of people that will never see himself for who he actually is, only that he's not his dad. That's where Taylor came from with the song idea, then when I was rounding it out, I realized that every business person I've dealt with I've outgrown, even though they've damn near tried to nail me to the cross just because I was moving on from them.
It's very difficult for an artist to overcome the scheming of the music business. It's a lot like the stock market or what I call "money guitar" — like the Moneyball movie featuring Brad Pitt about Billy Beane and the Oakland A's — because it's all data. The only difference between the music industry and the stock market is that, as corrupted as it is, there's actually regulation on the stock market.
[The Sagebrush Trilogy] came about when I made the deal with Island Records. I had been talking with a bunch of labels, but Island were the ones that really gave me creative and release control. It's the primary reason I signed with them and nobody else. It was right there in the paperwork — I do it my way and put it out even if you don't want me to.
When I signed the deal, we already had Lonesome Drifter done and Justin [Eshak, Co-Chairman/CEO] at Island hadn't ever heard it, which was another stipulation in my contract. I remember telling him that I planned to release a lot of records and to be ready, to which he responded by saying, "What if it was like a Cormac McCarthy Border Trilogy?"
I had already been thinking of doing something similar to Sergio Leone's Dollars Trilogy, so when I got back together with Shooter we started thinking of bigger thematic concepts instead of just a single LP. The throughline of it all is this concept of the Lonesome Drifter — a Waylon Jennings-type character showing up in Nashville in the '60s ready to disrupt and change the system, which he and others did.
What I've seen in Nashville lately looks almost exactly like what those guys were fighting against 50 years ago. It's like Mark Twain said — "History doesn't repeat itself, but it does rhyme." That's exactly what the Border Trilogy is about, telling that story through a Louis L'Amour type of character that's a stranger who rolls into an area where corruption got the town. It's like [the 1967 Burt Kennedy Western film] Welcome To Hard Times where there's a bad man in control running everything and everybody's too afraid to do anything about it — but not the tall, dark stranger.
Taylor and I started [writing "El Paso to Denver"] outside of the Plaza Theatre in El Paso. I had just finished the show, and we were doing an overdrive with double drivers to get up to Denver overnight. That's a long haul through the high desert mountains, takes about 12, 14, hours, you know, if you're hauling ass.
What it's more about is, I had a manager type guy tell me a few years back now, kind of courting me, he said, "Charley, any guy that's not a total dumbass can sell out arenas these days." I thought, Geez, if that's true, wow, how strange. And I thought, Well, maybe that's not a primary motivator for me.
I think an element of pop culture has always been disposable, but nowadays, more than ever, it's more reality and disposable-driven. We're seeing more forgettable content dominating our culture for a few minutes, and then it's gone. It's like, in the '90s, there was the birth of the 24-hour news cycle, and I would say in this era that we're living in now, it's the birth of the 2.4-second news cycle.
So one thing that I think about nowadays, [in the context of] "El Paso to Denver" is like, these businessmen, they all want me to turn into something that they think I should be while they're really just kind of staying the same. And the constant for me is that I'm out on the road. I've always been on the road, and I always will be. So for all of the bulls— going on out there, it's that idea that that's what it's all about for me. Playing in El Paso and knowin' I'm going to be playing in Denver the next day, that's my life. As Willie Nelson says, "It's not the good life, but it's my life." And I wouldn't change it.