Ryan Frank Cabrera was born on July 18, 1982, in Dallas, Texas. His father is a native of Columbia, and although Cabrera speaks only a little Spanish, he was influenced by Latino culture while growing up. As a boy he spent summers and holidays with his father's family in Miami, Florida, and listened to salsa musicians like Grupo Niche and Jerry Rivera (1973–). No one in his immediate family, however, was a musician and it was by chance that Cabrera learned how to play guitar. "I started playing guitar kind of by accident," he admitted on the Ryan Cabrera Web site. While in middle school he was inexplicably drawn to a beat-up guitar he found at a friend's house. One day he picked it up out of sheer boredom and began to experiment. Soon he was picking out chords to tunes by the Beatles.

He eventually began playing with friends and after many late-night jam sessions he formed his first band, a high-school punk group called Caine. "The music was just as bad as our name was," Cabrera confessed on his Web site. Cabrera fronted the band, which he claimed was a horrible mistake, since he was not a trained singer. It seemed that his music career would be short-lived, but then the budding singer had a kind of awakening after hearing the music of the Dave Matthews Band. Cabrera was specifically impressed by Matthews's guitar styling, and considered him to be a singer/songwriter with an edge. As a result, he decided that music was not just a hobby, it was something he wanted to devote himself to. Cabrera remarked on his Web site, "I said okay, this is going to be my life now. I have to start playing this music."

Cabrera put down his electric guitar, abandoned the fast-driving sounds of Caine, and formed a new acoustic-based band called Rubix Groove. With the help of his older brother, the band began playing gigs in and around Dallas, quickly becoming a favorite with audiences. According to Cabrera they played anywhere and everywhere, from restaurants to fraternity houses to birthday parties. Eventually, however, the band formed a loyal following and landed jobs at top Dallas venues, including the Gypsy Tea Room and the Curtain Club. While still in high school they also opened for such big name groups as Cheap Trick and Third Eye Blind.

Just as learning the guitar happened by accident, Cabrera went solo as a result of chance. For a surprise birthday present his brother bought a block of studio time. He only had enough money, though, for one person to record. While Cabrera was hesitant to record without his band, the opportunity was too tempting to resist. He went into the studio with three songs he had written, and the studio engineer was so impressed he offered to produce an entire album for Cabrera for free. The nineteen-year-old musician jumped at the chance, gathered up two years' worth of songs, and holed up at Deep Ellum Studios to create his first album, the independently produced Elm Street (2001). Cabrera played all the guitars on the CD, as well as keyboards, drum beats, and beatbox (creating beats, rhythms, and musical instruments using the human voice).