A huge fan of Elvis Presley, Frank Sinatra, Robert Johnson, and Muddy Waters, Hilton spent several years performing at open mic nights and clubs, and playing blues and jazz covers for tips in coffeehouses and restaurants. “I did pretty well with the older clientele because they loved that stuff,” Hilton says. “It wasn’t until I signed with Maverick that young people even came to my shows. I’d always be so shocked when a kid came up to me and said he liked my music, because usually it was: ‘Oh my parents heard you at the Crab Shack and they loved your rendition of ‘Wonderful World’ and I’d be like, ‘Thank you.’ And that’s when I got out of Palm Springs.”

Hilton moved to Los Angeles and released a self-titled independent album in 2000. He also indulged his other passion, acting, by appearing in The CW’s One Tree Hill and the indie cult favorite Charlie Bartlett, and playing Elvis Presley in the 2005 Johnny Cash biopic Walk the Line. (Hilton’s songs have been included on the Grammy Award-winning Walk the Line soundtrack and on all three of One Tree Hill’s popular soundtracks.) Hilton signed with Maverick Records and released The Tracks Of Tyler Hilton in September 2004. “I wrote all those songs when I was still in high school,” he says, “and I was very impressed that the songs I wrote while I was doing homework ended up being released on a major label. That was really exciting to me. I could have written those kinds of songs again, but I wanted to do better. And I think my new album is better.”