bailey struggled in school until he found his calling in his high school's drama department. he was soon performing in each school play and went on to study formally at the american academy of dramatic arts in new york city. he briefly attended santa barbara city college. he appeared in "almost famous", portraying jann wenner. he was seen in "center stage", "fight club", catherine jelski's "the young unknowns", "the scoundrel's wife", "seven and a match", renny harlin's "mindhunters" for miramax, and the independent feature "sexual life" for director ken kwapis.