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. His television appearances include Dawson's Creek, HBO's highly acclaimed series Band of Brothers produced by Tom Hanks and Steven Spielberg, and the HBO original film And Starring Pancho Villa as Himself opposite Antonio Banderas. Onstage, Bailey appeared in Equus at the Pasadena Playhouse, as well as Spoon River Anthology, Look Homeward, Angel, and Dinner at Eight at the American Academy of Dramatic Arts, Desire and I at the Access Theatre Santa Barbara, and Icarus' Mother at the SBCC Studio Theatre.
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. His television appearances include Dawson's Creek, HBO's highly acclaimed series Band of Brothers produced by Tom Hanks and Steven Spielberg, and the HBO original film And Starring Pancho Villa as Himself opposite Antonio Banderas. Onstage, Bailey appeared in Equus at the Pasadena Playhouse, as well as Spoon River Anthology, Look Homeward, Angel, and Dinner at Eight at the American Academy of Dramatic Arts, Desire and I at the Access Theatre Santa Barbara, and Icarus' father at the SBCC Studio Theatre.

