Charley Crockett Answers Critics, Explains History on Joe Rogan

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Joe Rogan has done some incredible things for the careers of independent country artists over the years, from being integral to the rise of Sturgill Simpson, to shouting out Tyler Childers and Colter Wall, to having Shooter Jennings, Charles Wesley Godwin, and others appear on his massive podcast. But if we’re being frank, not all of Joe Rogan’s musical episodes go especially great. As a musical novice, Joe doesn’t always ask the right questions, and sometimes the size of the audience makes guests pucker up (see Zach Bryan).

That was not the case with the recent appearance of Charley Crockett released back on June 19th. The interview resulted in some great revelations about Charley Crockett, answered some major questions and criticisms that comes up regularly about him, and generally speaking, portrayed Charley as a knowledgeable guy about country history, especially the Outlaw era, and self-aware of how he’s perceived.

With Crockett continuing to rise to the headliner level, it feels important to emphasize some of the most important revelations from the Rogan interview, especially ahead of Charley’s upcoming album Dollar A Day out August 8th.

You can find them below. The full interview is at the bottom.

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At the 27:00 mark, Charley Crockett talks about first learning to play guitar, and playing in front of his mother. Self-taught at 17 when his mother bought him a pawn shop guitar, Charley asked, “Mama, am I any good?” She answered, “Well son, when you play, people will believe you.” Charley Crockett has never been the “best” at anything, but that believably has turned out to be a key to Charley Crockett’s musical career.

At the 32:00 mark, Charley Crockett talks about how he probably didn’t wear shoes regularly until he was 9 or 10 years old, and that his half brother and sister (from a different father) were 10 years older than him. “They were pretty wild,” Crockett says. “I’m telling you that background because my brother became a hustler because he had to, because of a lack of education, because of poverty.”

Crockett went on to say that a bunch of people died, and a bunch of people went to prison. “We were in the paper, and I found myself not being able to get a bank account. Nobody I knew would go near me.”

This set the tone for Charley’s young adult years, and resulted in his decision to leave town and become a transient musician.

At the 41:00 mark, Crockett says one of the most prophetic things of the episode. “My mama said, ‘What happened to you when you were young wasn’t your fault. But now you’re a man, and it’s your responsibility.’ I’ve been living off of that for a long time.”

At the 54:00 mark, Crockett explain how he got discovered, giving credit to Evan Felker.

“I was standing out at Gruene Hall handing out CDs on a street corner ’cause I couldn’t get into the show. Handed a guy a CD. His name was Evan Felker. I didn’t know who he was at the time, but he was the front man for the Turnpike Troubadours. He took home and listened to it with his then girlfriend, now wife. Lo and behold, his agent Jon Folk called me up and started booking me.”

Jon Folk was the founder and CEO of Red 11, which booked a lot of the Texas and Red Dirt acts at the time. They were sold to WME in 2023.

At the 57:30 mark, Charley Crockett explains how he owned Willie Nelson’s Red Headed Stranger bus for about a year. This was around the time he started experiencing heart issues that eventually led to him having heart surgery.

At the 1:07:00 mark, “I think mental slavery is something that is real. But so much of it is us. We do it to ourselves. I remember something [Noam Chomsky] said a long time ago that stuck with me where he was talking about American consumerism over the last hundred years. He said, ‘There are people working really really hard to eliminate your sense of purpose for the explicit goal of making you a more efficient consumer. All human being live for and desire a life of purpose.’ The 10,000 hours, the ten years.”

“I kind of realized when I became a transient that a lot of who I was was this amalgamation of a bunch of people just trying to f–kin’ sell me products—’90s radio just blasting my brain as a kid. So much programming is hard for me to watch because you know that it’s only a vehicle for the commercials … I feel like I killed a lot of the false version of me that I was becoming that I only realized when I walked away from Crystal City. And then I really started becoming me.”

These two quotes are really important to understanding who Charley Crockett is. A lot of people have pulled up footage of him performing on subway cars in New York City from many years back, citing how this means he’s not really who he’s selling himself as. Crockett would address this in greater detail later in the Rogan interview. But these thoughts set the table for them.

Crockett’s observation of “it’s only a vehicle for the commercials” is also a great way to understand commercial country radio, and why it operates like it does.

At the 1:13:00 mark, Crockett talks about the importance of being a Texan in music, and how that makes it unique. He specifically tells a story of performing on the streets of Copenhagen, and how his money quadrupled when he leaned into his Texas roots. You hear this from many Texas performers who’ve often found greater reception for their music in Europe as opposed to the United States.

At the 1:18:00 mark, Charley launches into a deep discussion about Waylon Jennings, Willie Nelson, the mid ’70s in country music, and the Outlaw movement that revolutionized country music at that time. His knowledge of this era is detailed, and you can definitely tell he’s tried to use this knowledge to the benefit of his own career. The only caveat that always seems to need to be cited in these oral histories of the Outlaw movement is to give credit to Bobby Bare, who was truly the first to break free from the Nashville system and gain creative control, while Tompall Glaser also played a major role by setting up the renegade studio at Hillbilly Central.

At the 1:23:00 mark, Crockett says, “When I got signed to Thirty Tigers in Nashville, it was purely because Jon Folk was my agent, and those guys they’ll tell you this themselves, they didn’t understand what I was doing. They didn’t get it. I was only put on the roster as a favor to my agent because they were having some success with some other artists.”

In the Rogan interview, Crockett gives a ton of credit to booking agent Jon Folk, but in numerous instances, tends to diminish David Macias at Thirty Tigers, and the Thirty Tigers record label. Crockett also complains about how many labels push a two-year record cycle, while as we know, Charley Crockett likes to release two albums a year, if not more. But Crockett was able to do two records per year through Thirty Tigers for multiple years.

Crockett later goes on (1:27:00) to compare Colter Wall leaving Thirty Tigers to Willie Nelson leaving RCA back in the ’70s, which allowed Waylon Jennings to stay on RCA, but negotiate complete creative control.

“Colter to me is kind of like when Willie left RCA back in the day,” Crockett says. “And when he left, all of a sudden, those guys [Thirty Tigers], because he took everything with them, were about to lose me, and they handed the fu–king keys over to me.”

Whiskey Riff went on to publish an article that mischaracterizes Charley Crockett’s relationship with Thirty Tigers, and the Thirty Tigers relationship with all of its artists. One of the things that makes Thirty Tigers unique is they do not sign multi-record deals with artists. An artist can leave at any time, which Colter Wall, and eventually Charley Crockett took advantage of. So did other major artists like Luke Combs and Sturgill Simpson. Sturgill ended up coming back to the label after becoming disillusioned with the major label system.

Another important aspect of Thirty Tigers is all artists have complete creative control. In Whiskey Riff‘s portrayal of this portion of the Joe Rogan interview, the article claims, “Colter didn’t just leave his music behind, and he took his catalog of music and everything with him, which paved the way for Charley to gain creative control with Thirty, because they didn’t want to lose him too.”

Whiskey Riff also goes on to say, “If it wasn’t for Colter walking and going to a new label, it’s unlikely Crockett would’ve maintained that kind of creative control because that’s simply just rare for any artist, regardless of how big the label is…”

When asked about Charley Crockett’s exchange with Joe Rogan and Whiskey Riff‘s portrayal of Thirty Tigers and creative control, David Macias told Saving Country Music point blank, “All of our artists have creative control over their musical output. Always have, always will.”

The “handing the keys over” that Crockett mentioned to Joe Rogan was a better percentage deal on the money split with Thirty Tigers. Creative control was never in question. Thirty Tigers also facilitates each artist owning their own record label. For Crockett, it was called “Son of Davy.” Thirty Tigers just distributes the music.

What has happened over the years is since Thirty Tigers does not restrict artists by signing them to multi album deals or disallowing them to go to other labels, majors have regularly picked their pocket. Tyler Childers also started on Thirty Tigers before moving to RCA. Thirty Tigers has developed so much of the top independent country talent today, including Charley Crockett. The majors then come in a pick them off, taking advantage of the Thirty Tigers open door policy.

Crockett signed with Island Records right before the release of his last record Lonesome Drifter. Perhaps Crockett felt Thirty Tigers was too small potatoes for him at this point in his career, and Island likely offered him a major signing bonus. But Thirty Tigers never restricted Crockett’s creative control, or made him adhere to a 2 year album cycle. Later in the interview (about the 2:01:00 mark), Crockett calls his Thirty Tigers situation a “broke dick deal” because they would only spend $10,000-$15,000 to market his albums.

The first time Saving Country Music (or really anyone) ever wrote about Crockett was in September of 2017, right before Crockett released the album Lil G.L.’s Honky Tonk Jubilee, which included Charley’s now famous cover of “Jamestown Ferry.” David Macias reached out to SCM personally to ask to preview the album a week early in hopes of starting the national buzz for Crockett ahead of his next original record, Lonesome as a Shadow.

At the 1:42:00 mark, Charley Crockett gives great sermon about what it means to be a music artist from Texas.

“One thing you can’t explain away is place. You can’t explain away region. You are from where you’re from. It’s not that it’s rock, blues, soul, or country. It’s Texas. And what happens with Texans of any background is they discount you for sure, look at you as provincial. People have ideas of what Texas is who’ve never stepped foot in the state.”

“There’s two roads for a Texas artist. You either let somebody in Nashville or New York or L.A. convince you to lose your accent, wash the Texas off, do it our way. Or—which is the only way—which is to take your brand of Texas to the world, whatever it is.”

At the 2:05:00 mark, Charley Crockett explains that he made a movie called $10 Cowboy that involves in part the liquor store called Waymore’s in the hometown of Waylon Jennings, Littlefield, TX, operated by Waylon’s brother. The store also includes a shrine/museum to Waylon in a side room. When Saving Country Music stopped by Waymore’s in 2024, it was right after Crockett had been there, and James Jennings mentioned the taping of the movie. Crockett left it open if the film would ever come out, but it’s definitely something to keep on the radar.

At the 2:10:00 mark, Charley Crockett address the criticisms against him directly, and very specifically the common criticism that comes up from some people who love to cite a YouTube video of him performing in New York City subway cars.

“I’ve always been a pretty polarizing figure for some reason with audiences. It’s a love hate thing. And I’ve done a lot of styles, and they’ve called me a stylistic chameleon … I can play the blues, I can play country music, I can play folk music. I played all that shit on the street, matter of fact. It’s surprising to me that people would question my authenticity and point to me playing in subway cars as this ‘ah ha!’ moment that I’m not who I said I was. Why don’t you try to play in those New York City train cars? Brother I’d rather get on a fu–in’ bull.”

At the 2:20:00 mark, Charley Crockett goes into even greater detail about his experience playing on the subway trains, who he was playing with, and why. He also explains earlier in the interview how he was almost signed to a record deal off the trains, but didn’t think he was ready.

At the 2:16:00 mark, Charley Crockett says, “Waylon Jennings was always rock and roll. He was never traditional country. There’s nothing about him if you know what you’re listening to, even on his very first record, there’s nothing straight ahead.”

Though Crockett offers tons of great insight into the Outlaw era in the interview, including in this segment, he overlooks the importance of steel guitar legend Ralph Mooney to Waylon’s sound. Mooney was a country legend even before he joined Waylon’s band, and it was Mooney who kept Waylon’s more rock-oriented sound grounded in country.

At the 2:34:00 mark, Crockett says, “The manager in many cases, is the most powerful, and the least regulated.I think that’s what’s wild about the music business, there’s basically no regulation.”

Crockett recently brought his management totally in-house, meaning he’s no longer working with an outside manager after working with half a dozen different guys and companies over the last many years.





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