Photograph of Caleb Caudle by Joseph Cash

The Long Road to the Opry Stage

From punk rock roots to Americana success, Caleb Caudle discusses his evolution as a songwriter and the path that led to his upcoming Grand Ole Opry debut.

By Chuck Reece

Sep 19, 2024

Caleb Caudle was in his twenties, just beginning to move out of the punk rock milieu and into the hope of becoming a masterful songwriter, when two of his friends in Charlotte, North Carolina, asked him to write a tune for their fifteenth wedding anniversary. That song—called “Miss You Like Crazy”—made me a Caleb Caudle fan.

Those friends must have had a fine marriage—a coupling of two forceful personalities who fight a little but have learned how to recover, because they know that, ultimately, they’re made for each other. Caudle wrote into that dynamic, and the way he rolled into the chorus of the song just caught my ear and stayed there.

We’d fight like my grandfolks, John and Rose
But if the Lord takes you first, he better take us both
’Cause I’d miss you like crazy

It’s hard to write a line like “If the Lord takes you first, he better take us both”—because there is a full page’s worth of meaning behind those eleven words. First, you learn these people were raised in a culture where people do not simply “die”; the Lord “takes” them. Second, you learn this couple feels one of them isn’t really worth a damn without the other. Finally, you learn that when something forces them away from each other, something even stronger begins pushing them back together.

I’m a hopeless sucker for a song lyric like that, where much meaning hides behind a few words. That’s why, after I first heard Caleb Caudle sing “Miss You Like Crazy.” I wrote this: “In a just world, the song would be on every country radio station in the world, and Caudle would be a millionaire.”

Caleb Caudle is still not a millionaire. But here we are, exactly ten years later, and Caudle’s latest album, Sweet Critters, is sitting at No. 23 on Billboard’s Americana chart. And on November 23, he will make his debut on the stage of the Grand Ole Opry in Nashville. Over that decade, I’ve always followed Caleb’s career, and I’ve gotten to know him personally. I’ve watched him go through downs, then ups. Seen him lay down the bottle after too many battles with it. Watched him a marry a fine woman named Lauren, who has played a critical role in his growing career and with whom Caleb just celebrated an eighth wedding anniversary. Once, he visited my house and played a Tom Petty song for Stacy and me while we all sat at our kitchen table.

“I tell people all the time, Caleb is the hardest working man in show business. He’s an example of how you don’t have to have a major label deal, and he still makes it work.”

—John Paul White

When Sweet Critters, his sixth album, came out a couple weeks ago, I was taken by Caleb’s singing, how it has become more precise, more adventurous, a truly fine instrument. On this album, it is surrounded with Appalachian acoustic instruments, played by his very own road band and produced to a fine sheen in Muscle Shoals, Alabama, by another great songwriter, John Paul White, formerly of the Civil Wars, and his musical partner Ben Tanner, formerly of the Alabama Shakes.

I also heard how Caleb’s songwriting has matured. Now, at age thirty-eight, he can pull off complex character studies—lyrical and literary—of the sort that “Miss You Like Crazy” only hinted at a decade ago. Sweet Critters’ title song, in just two minutes and forty-one seconds, spans the marriage of Gerry Ann, who “collected feathers and little brass figurines,” and Harold Lee, who “split the wood and put vinegar on his greens.” It’s like a novel in miniature, following the couple from when they “met so young” all the way through the years when Gerry Lee must help Harold Lee because he’s “struggling with the stairs.”

Ten years ago, Caleb Caudle gave up paychecks and set out to be a musician. I’ve watched him perfect his art and, with the help of Lauren, learn to navigate a notoriously treacherous business. I figured it was time to talk about how he figured out how to do both without ever having to take a straight job again.

“I tell people all the time, Caleb is the hardest working man in show business,” John Paul White told me. White, besides running a record label and studio in Florence, now also teaches aspiring musicians in the University of North Alabama’s Entertainment Industry program. “It’s fascinating to me what Caleb and his wife have accomplished pretty much on their own. It’s a great success story. I tell students here at UNA about how he’s put it all on his back. He’s an example of how you don't have to have a major label deal, and he still makes it work. And that’s the definition of success.”

When Caleb and I talked, I asked him to dial back the clock to his first album, Paint Another Layer on My Heart, which contained “Miss You Like Crazy,” the song that first hooked me.

Caudle: When you met me, it was around Paint Another Layer, and that really did feel like, “Hey, I’m going into a big studio and we’re making this record, and I’m hiring people.” I had signed with a really small indie label. Around that time is when I gave up any other source of income. I just switched to music.

Reece: When you look back over the last ten years since that first record, how do you see your career development? I ask that from two points of view. One would be you learning how to make a living in this business, and the other one would be as a songwriter, an artist.

Caudle: Those are totally separate, right? It probably took me the better part of a decade to figure that out, that those two things were separate and that they should remain separate. So it’s a decade, and so obviously, a lot has happened. We also had a world pandemic, which was a whole other thing I had to navigate and figure out. But prior to that, I always viewed each record as a stepping stone. I never thought of anything as being like, “Hey, I’ll put out Carolina Ghost (his second album), and that’ll be the finish line. That’s where I’ll get the glory.” Because when I look at my favorite songwriters, they don’t treat their careers like that. I certainly don’t think John Prine put out his first record—with all those songs like “Hello in There” and “Sam Stone" on it—and just felt like he was done, you know? Sometimes it feels like there’s a lull, and we’ll go six months and nothing big happens. But in that interim, I’m working on the day-to-day stuff: how can I get smarter about the business side? How can I get smarter as a writer? How can I become more vulnerable as a writer, and how can I inject all of myself into my work?

When you’re approaching that first record, you’re like, “Man, I can write about anything! I can write about falling in love. I can write about the first time I felt heartbreak, the first time I lost somebody who was close to me.” As time goes along, I have had to mine this new area—like, what am I forgetting from my past that is evocative? And how can I incorporate that into a character study of somebody new? And so now I write way more character studies.

I know we talked about “Miss You Like Crazy” on that first record. I think that was the only character study I had written until that point, and it wasn’t by design. Somebody had reached out and asked me to write a song for them, and they gave me the details. Okay? And so that was kind of my blueprint for character studies. Now, instead of somebody giving me the details, I need to mine my own experiences and pull from that and use those as details and create characters.

CONDENSED-Caleb-Caudle_Sweet-Critters-album-cover

As far as the business side goes, I’ve had to keep my antenna up, and I’ve had to constantly stay aware of what the changes are, because everything changes. With each record coming out, it’s a whole new landscape each time. I’m really benefiting from Lauren working behind the scenes as a project manager, because she can clue me in: “Hey, you know what, what you did two years ago isn’t what’s happening now, and you have to adapt.”

Reece: You’re talking about how fast the business is changing, right?

Caudle: Absolutely. It’s like, every two years, here’s a new set of rules I have to play by to have the best chance to get the record in as in front of as many people as possible. And that has nothing to do with the art.

I have a lot of great mentors who have taught me what they know. And that list of people, it’s grown. Ten years ago, if you had told me Buddy Miller would text me about my record, my head would have blown. And that’s just one example.

The business is constantly changing, and I’m trying to rely on my team. I have an entire team around me now. I’ve got a manager, a booking agent, a booking agent overseas, a publicist, a radio person. So I’m kind of in the center of this big web of people that I work with, and I’m running point on all that. I have hired the people who I trust to give me the best advice at my blind spots. Obviously, I wasn’t able to do that at first because there was no money there. But time goes on, and you’re able to add a piece at a time. Over time, I could attract management, attract an agent, and take some of that off my plate, and really free me up to start planning. What does the next five years look like, versus what does the next five hours look like? That was a real problem for me. And I feel like I’m finally at a good place, where we are planning out the next two or three years. It feels good.

Reece: Let’s talk about those mentors some more—the primary people who’ve helped guide you along.

Caudle: The first artist who really changed things for me was [SiriusXM Outlaw Country channel DJ and songwriter] Elizabeth Cook. She took me on tour twice. Not only did she take me along on tour, which nobody had done, but she had me come out and sing with her each night. She invited me to Outlaw Country, which was the first time I’d ever had any sort of national radio. She went to bat for me. Then also John Paul White is a huge, huge mentor for me. Obviously, he produced the new record. Back in 2018, we were on the Cayamo cruise together, and that’s how I met him. He asked me to be part of a Don Williams tribute. I sang “Atta Way to Go” [a song from the late Williams’s 1974 Volume Two album].

Caleb Caudle joins John Paul White for a Don Williams number on the Cayamo music cruise in 2018.

We got to be fast friends. We’re a lot alike, me and John. We’re both from the middle of nowhere in the rural south. And whether we’re making overtly country music or not, we’re going to get a country tag on us, no matter what. Elizabeth’s the same way. They have the grit and the sweetness, right? I really love writers who have those two sides. Buddy’s a big example. Guy Clark’s a big example. It’s just these people who can kind of get down in the mud, and then they can kind of get out into the perfectness of nature.

I try to ride that line and show both sides of life. I never want to get too flowery and I never want to get too down and out. I think I exist somewhere between those two things. Sometimes I’ll dip further into one than the other. And so you have a song like “The Brim” on the new record, which is very sweet, and then you have a song like “Knee Deep Blues,” which is gritty.

Reece: I feel that in the title cut of Sweet Critters. It feels like maybe the best character study song you’ve ever written. There’s an emotional maturity in that song about a long relationship between a man and a woman that you wouldn’t have been capable of when I first met you.

Caudle: No, definitely not. There’s something that happens in that song that I’ve never done in any song. I don’t know if you picked up on it, but the line, “His ankle hurts when it rains” is a precursor to him struggling to get up the stairs later in the song. I’ve never developed a character in a song to where I could foreshadow in that way before. I was really proud when I finished that one. I thought, job well done.

I’m kind of at the point where I’m writing for me, you know? I’m not writing for Is this going to be a single? If I can make myself feel good about what I’m writing, which is a huge task, then I’m just ready for the world at that point.

Reece: You should be proud. The thing that makes “Sweet Critters” so rich is the level of detail in it. You open by talking about how Gerry collects figurines and Howard puts vinegar on his greens, and those were great little details.

Caudle: Thank you. If you can figure out how to write someone’s habits or ailments into a song and you can do it in a way where you’re you’ve taken yourself out of it, and you’re just letting it breathe and letting it live, I think that’s what makes it realistic. There are certain things that you kind of need to stay out of and observe about other people.

Reece: Let’s talk about “The Devil’s Voice.” It’s about a hard-drinking young woman whose signature quip is “The devil’s voice sounds a whole lot like mine.”

Caudle: It’s another character study. We’re dealing with an addict in the song and so obviously, that’s a huge piece of who I am. But I wanted to approach it maybe from a different angle. And I wanted to just not judge. I try not to judge the characters in the songs. I don’t think that’s my place as a writer. It’s sort of like I reveal the story and leave enough for the listener to make their own judgments or not. Or to question themselves: why am I judging this character?

I felt like with Sweet Critters—and with Forsythia, the previous record—I unlocked some magic as far as getting more detailed with my writing. I’m kind of at the point where I’m writing for me, you know? I’m not writing for Is this going to be a single? I think I’m just trying to impress myself at this point. If I can make myself feel good about what I’m writing, which is a huge task, then I’m just ready for the world at that point.

Reece: And I think that brings up another question. You’re playing in a lane where—and I don’t want to mischaracterize this, so please correct me—it’s not like you’re working in Nashville trying to get a cut of one of your songs onto some big star’s record. I mean, if you got a cut, that’d be great...

Caudle: I do have a publisher now, and that’s a pretty recent thing. I’ve signed a publishing deal, and, you know, if I get something cut, amazing, but, yeah, it’s not my focus. My focus is the art.

Reece: When you say you’ve gotten to the level of maturity—and you’ve gotten your team built up—to where you can look a few years down the road and think about what you want for yourself, what do you envision? What do you see when you think about living life the way you want to live it, and doing what you feel like you were put on Earth to do?

Caudle: In a lot of ways, I’m already doing it, but that’s still not enough. I don’t mean that not about financial success. It’s the yearning to just top myself, right? Maybe I’m already there, or maybe I’ll never be there. But I operate as if I’ll never be there. Maybe that’s bad, you know…

Reece: I think, in a lot of ways, that’s the nature of being a writer…

Caudle: Yeah, or an artist in any way. I think everybody can relate to that if they’re creative at all. In a lot of ways, I’m already doing what I want to do. I just want to be able to do it on maybe a bigger level. I’m doing everything I know how to do to further this thing down that road. But as far as the art is concerned, I feel like it’s in a great place now, where I’m remaining completely open and completely curious. I think that as long as I can stay in that realm, I can keep working at a very high level, where my standard of writing is constantly growing. Just looking to the people who I pull inspiration from, and seeing how they navigated their careers and how it looked as time went on… You look at Mary Oliver and Wendell Berry, just crushing it in the writing game later in life. That’s so inspiring for me, because it just feels like the work will never run out. I’ll run out before the work runs out.

Having him push me to get it right...was awesome. It could only happen like that because of how much trust I have in John. If it was somebody else telling me to do that..., I would have just been like, “Get away from me!” But I really, I really trust John.

Reece: Let’s go back to one of the mentors you were talking about, John Paul White. How did you first get to know John Paul?

Caudle: Just through him asking me to be part of that Don Williams tribute. We just hit it off. I think the next time we saw each other, we were over in London for Americana Fest UK. I remember it was snowing, and we were in Hackney, and we just sidled up to a table together and just hung out all night. Super easy guy to talk to, and we share a similar sense of humor—a dark one. We’re just similar in general—how we view music, how we interpret it, and how we hear it. And I’ve always been just blown away by his voice.

Reece: He does sing like an angel.

Caudle: When we were in the studio, I mean, he just pushed and pushed and pushed me to become a better singer. I was already starting to do that around Forsythia. I was really starting to feel like I understood what I could and couldn’t do with my voice. So having him push me to get it right, it was awesome. I had never experienced that sort of drive from someone to get the best out of me before. It was just a lot of fun. And it could only happen like that because of how much trust I have in John. If it was somebody else telling me to do that, my punk-rock background would have kicked in. I would have just been like, “Get away from me!” But I really, I really trust John.

Reece: What was it that made you decide it was time to go to Alabama and work with John Paul and Ben? You made you last two records—Better Hurry Up and Forsythia—at a pretty amazing place, the Cash Cabin, with John Carter Cash and some other pretty heavy hitters, like Sam Bush and Jerry Douglas.

Caudle: I remember having a conversation with my buddy Trey Call, who is kind of the default house engineer at Cash Cabin—he engineered Forsythia—and I played him some of these new songs. I went by the Cabin one day when I was in Nashville, and he threw up a mic, and I played him some new stuff. We were talking about what my plans were. I said, “You know, I could I could probably make every record from here on out at the Cash Cabin.” I love that place so much. It immediately felt like home for me when I went in there to record Better Hurry Up. And Trey just looked at me and he goes, “Don’t get too comfortable. Just because you can record everything here, it doesn’t mean you always should.”

As soon as that you start getting comfortable and you’re like, Oh, I could do this for the rest of my life, that means that I need to go get uncomfortable again. I had a few different people who wanted to produce Sweet Critters, and I talked to everybody, anybody that was interested. I had phone calls. I met with people in person, because I wanted to get it right. I wanted to make the right decision. I wanted to do my due diligence and explore all options. I played somewhere with John Paul, and I was talking to him backstage, and I told him, “Look, I have these songs. My band uses Appalachian instruments, but not completely in the way that most people use them. I really I need to find somebody who can believe in this idea of mine, that something can be very traditional and very nontraditional at the same time, and those things can can work together to push this type of music forward. I want to become a gateway to country music the way that the Byrds’ Sweetheart of the Rodeo was.” That’s what I wanted, because that led me to Merle Haggard and everything else. I started realizing that country music doesn’t have to be this square thing that is only meant to recreate itself. It can be more vibrant, and it can explore a lot. Through the Byrds and Gram Pasons, I got to know who Townes Van Zandt was. And Guy Clark. And John Prine.

So, I always kind of thought it would be cool if my records could lead somebody to the stuff that those those folks led me to. I want to be able to usher younger crowds into those folks, if they haven’t already gotten there, right? And John Paul just bought into that. He was like, “Yeah, that’s how I view music.”

Reece: I want to talk a little bit more about the making of this album, because when I listen to it, I can hear something in it I don’t know that I’ve heard on one of your records before. But I’m not sure exactly how to describe it…

Caudle: Like I’m calmer?

Reece: Yes!

Caudle: I know what you’re talking about. I recorded it in a different way than I ever recorded before, which was I went down to Florence and I recorded everything, just me and my guitar, solo. And then we recorded the band live to those solo tracks.

I’ll be honest with you: right now, everything—all my hopes, all my dreams for my career, all my bucket list items, the things I want to do—it all at this point just feels inevitable. I just got to stay in the game.

Reece: Tell me how that worked.

Caudle: I had heard that was the way Guy Clark recorded later in his career. He would just record himself solo, and then he would have his friends play on it. And that got me very interested, because you’re allowed to be more intimate with it. You know, you’re not sharing it with anyone. And so when I was in the studio, it was just me, John, and Ben. John would come in after every take, and we would talk about what was working, what wasn’t working, and if there was a line that I needed to focus on. He would say, “Hey, just give me something different on this one line than you gave it to me last time.” I had rehearsed and rehearsed and rehearsed going in. The calmness you’re hearing is probably because I’m not singing over a band. I’m just singing over my guitar.

Reece: Okay, tell me how this whole Grand Ole Opry debut thing feels.

Caudle: It’s great. It was a good call to get. I can’t remember a time not knowing what the Opry was and what it meant. I’m excited. I fought to take the band with me to play, which I’m really excited about. [Often, singers who play the Opry perform with the show’s house band.] And John Paul’s going to come up from the Shoals, and he’s going to sing with me. I’m pretty pumped. It’s something I’ve wanted to do for a long time. Probably since the first time you met me, I’ve wanted to do that. I’ll be honest with you: right now, everything—all my hopes, all my dreams for my career, all my bucket list items, the things I want to do—it all at this point just feels inevitable. I just got to stay in the game. That’s it. I mean, that’s what any of my heroes would tell me: just figure out a way to make the next record and stay in the game. And you know, all the things you want to do, it’ll happen.

Reece: You know, sometimes, when you get in that right spot, you got to be able to recognize that you’re in it, and then just sit in it and let it happen.

Caudle: I’m so much happier that it happened now rather than eight or nine years ago. I would not have been ready for that type of moment. It’s a good lesson in patience. It’s a good lesson in perseverance.

Chuck Reece

Website

Chuck Reece is the co-founder and editor-in-chief of Salvation South, the weekly web magazine you're reading right now. He was the founding editor of The Bitter Southerner. He grew up in the north Georgia mountains in a little town called Ellijay.