Bailey attended Duke University in Durham, North Carolina, on a full athletic scholarship. He graduated in 1995 with a degree in Psychology. After graduation, Bailey moved to Los Angeles to pursue his acting career, which has encompassed a training stint in London and performing in such plays as "A Comedy of Errors," "Picnic" and "Death of a Salesman." Bailey's first film break came in Adam Shankman's Cosmo's Tale (1998), which screened at both Sundance and Cannes in 1999.