Eion struggled in school until he found his calling in his high school drama department. Eion was soon performing in each school play and went on to study formally at the American Academy of Dramatic Arts in New York City.
On stage, Bailey has appeared in Peter Schaffer's classic psychological drama, 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 appeared in a cameo role in Cameron Crow's Almost Famous, portraying Jann Wenner. Bailey's TV appearances include Dawson Creek, Band of Brothers and the HBO original film And Starring Pancho Villa as Himself opposite Antonio Banderas.