After developing a following in the Houston area, Carll signed a one-album deal with Compadre Records, releasing "Flowers and Liquor" in 2002.
The follow-up, "Little Rock," was released under his own label, Highway 87 Records and produced by R.S. Field. The CD became the first self-released album to reach number one on the Americana music charts. In May 2006, Carll announced that he signed with Lost Highway.
Despite the respect Carll obviously has for those he admires, he was once blessed with the chance to write with Guy Clark and didn't turn it down. "I always find it's difficult to write with somebody, no matter who they are," he explains. "It can be an awkward experience because you completely have to open yourself up and throw out ideas. I think Steve Earle said it's like letting somebody watch you have sex. You're completely opening yourself up."
"Working with Guy was a great experience," he recalls. "We met at a party one time. We did a show together somewhere in Texas and afterwards hung out and had a few drinks and talked a bit. I was coming through Nashville so I just called him up and said, ‘You probably don't remember me, but we met at this show. Would you like to write a song together?' And much to my surprise, he said, ‘Sure.' So I went over to his house. I tried not to think about the fact that he was one of my songwriting heroes and just tried to sit down and get on the same level and write a song together. Eventually I threw out some ideas, and he found one he liked, and we started working on it. It was a great experience, in that there's no songwriter's school. You're just trying to figure it out on your own when you're coming up. I'd never had anybody show me any tricks or gotten to really see how they work, and with Guy it was really a good education watching him work on the craft of a song and see how he approached it -- with each line and the emphasis he put on each and every single word, which was somewhat different from how I approached things. Not only did we get a song that I liked out of it and he was extremely gracious and great to hang with, but I thought I learned a lot in a short period of time."
Ironically, one other cover song on this disc is "I Don't Wanna Grow Up," which Waits – the songwriting inspiration for "Bad Liver and a Broken Heart" – helped write. "That was one where I heard his version and then I heard -- I believe it was The Ramones -- do a version of it. And I'm sure several other people have recorded it as well. That's another one, where just the truth behind it and the kind of humor and universality of it jumped out at me. That's something that everybody can relate to – not wanting to grow up. Not wanting to have to have all the worries and the stress and the mortgages and the heartbreak and the reality of adult life. And just wanting to hang onto that innocence and youth for as long as you could. If I cover something, I try and put my own spin on it, performance wise, and I heard those (by Waits and The Ramones), and I thought they were really cool versions. But I thought that I could do it a different way and still have that message come through, but kind of do it my style."
"It's hard for a kid to grow up," Carll relates. "All they know is their youth. And you want to grow up as fast as you can and do all the things that seem like they'd be a lot of fun when you're younger. But with that, comes the things that aren't as much fun. If you could know then what you know now, you'd probably enjoy your youth a lot more. But that's not the way it goes so we have to sing about it so that kids will get it."
Carll, who grew up in the Houston suburb of The Woodlands, is a college graduate who majored in history and minored in theater at Hendrix College in Arkansas. But music was more important to Carll than using his collegiate education after leaving the university.
"I always thought I was going to be a songwriter," Carll confesses, "and I was just kind of biding my time going to class occasionally and doing just enough to not get kicked out. That was a time in my life where I was away from home, living in a different place and soaking up the different experiences that came with it. I just thought this was a great time in my life to learn as much as I could, but after about a year in school in Arkansas, I had pretty much decided that when I got out I was gonna go try and be a songwriter. I was just hanging out and living for a few years and trying to come up with some experiences to write about. At that point, I hadn't really done anything, and I didn't feel like I was ready to move to Nashville or move to Austin or something and give it a shot. I was enjoying myself."
‘I remember going to my counselor when I was about to graduate -- and I graduated last in my class. So having a 2.1 GPA with a history degree and minor in theater, I wasn't very employable. And going up to my counselor I said, ‘Okay, well I'm about to get out. What are your recommendations?' He said, ‘Well, you could go to graduate school.' ‘Well, I don't think four more years of school are gonna do it for me.' There really was no other job - other than teaching high school or something - that my degree and my grades was gonna allow me to do. So, I just moved down to the beach and started singing in bars."
It doesn't always turn out this well, but Carll went from last in his class, to becoming a first class songwriter.