Bailey left college and spent the mid-1960s working at local theater companies before moving to California in the mid-1970s, where he landed roles on television programs of the day such as Starsky and Hutch and Charlie's Angels. His film debut was in A Force of One (1979), an early Chuck Norris film. He then got his breakout role as Rizzo in M*A*S*H. He also did a star making turn as Tom Berenger's sidekick in Rustler's Rhapsody (1985).
In the late 1990s he starred in three of the seventeen television movies and miniseries in the Bible Collection series produced for the TNT television network, Solomon (1997), Jesus (1999), and Paul (2000).
He returned to college in 1993, and graduated from Texas State University in San Marcos, Texas in May 1993, with a Bachelor of Fine Arts, Theatre. For the 1999–2000 school year, he was the Artist-in-Residence.
Since 2001, Bailey has served as the Executive Director of the Sunshine Kids Foundation, which provides trips and activities for hundreds of young cancer patients annually. He first volunteered with the organization after his goddaughter was diagnosed with leukemia.
