Born in Minneapolis, Bailey has been acting from a young age. His film credits include M. Night Shyamalan's The Happening, starring Mark Wahlberg; Coraline with Dakota Fanning; Dragonfly, starring Kevin Costner and Kathy Bates; and Mission to Mars. Bailey played the lead role in Hallmark Hall of Fame's Little John, as well as starring roles in NBC's Behind the Camera: The Unauthorized Story of Diff'rent Strokes and VH1's Too Legit: The MC Hammer Story.
In television, Bailey most recently completed four years as a series regular on NBC's The Night Shift. He had a recurring role on Becker, which garnered him a Young Artist Award. He was also a series regular on Wanda at Large and had guest-starring roles on ER, The Practice, Touched By An Angel and Shameless, to name a few.