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Cleaves switched to playing guitar while in college, he explains, "because I was a keyboard player in the band, and I was always the sideman. And I wanted to have my own band and be the band leader and singer and all." At the same time, he "rediscovered roots music" via Bruce Springsteen's Nebraska album. "And through The Clash. They were pointing toward rockabilly and some things, and hearing about Joe Ely. And even The Stray Cats, who I saw on television, and thought, 'Wow, that's cool stuff. I'm sure my father has some of those old records in the attic.' And sure enough, I went up there and just raided the whole record collection gathering dust in the attic. Taped all this Buddy Holly and Gene Vincent, Elvis, Hank, and Woody."
Cleaves took those tapes and his father's guitar with him to Cork, Ireland, for his junior year abroad. "I followed a girl over there," he confesses. "She basically dumped me on the plane. So there I was, committed for nine months, with no girlfriend, no car, no job, no TV, no friends, no family. So I ended up with nothing to do but learn songs and play on the street. That really got me started with the singer-songwriter thing. If that hadn't happened, I wouldn't be here today. And that happened a couple of times down the road too, in other scenarios, when I was about to quit. And that kind of thing just pushed me over the edge into desperation to try it again."
After he graduated from Tufts, Cleaves' life fell apart again in 1988. "So I started traveling around some and playing, sleeping in my car and on couches. And I ended up in Portland [Maine] and started getting gigs in bars. And after a few months, I was making enough to survive on. I couldn't believe it. I was so happy. It was the happiest year of my life." Since then, he's been making a living at music, aside from the occasional stint as a pharmaceutical guinea pig, ingesting new drugs at Austin's Pharmaco drug-testing facility, and renting out his sound system and mixing talents.
He eventually found that Portland wasn't big enough to use as a springboard for his career. Austin was a natural, and it also provided a respite from the Maine winters. "I really wanted to be up close to people like Joe Ely, because my heroes at the time like Bruce Springsteen and Tom Petty were so unapproachable," Cleaves recalls. "But I knew that someone like Joe Ely was also a hero, but someone I could see, often, and maybe open up for. I was just looking to be in that kind of scene, where there were a lot of people I could look up to and learn from. I didn't have much evidence for that, but my instincts turned out to be right."