Bailey was born in Port Arthur, Texas. He went to Thomas Jefferson High School in Port Arthur with Janis Joplin and Jimmy Johnson. He started college at Lamar University in nearby Beaumont and transferred to Texas Tech University in Lubbock.
Bailey left college and spent the mid-1960s working at local theater companies before moving to California in the mid-1970s. He broke into television with a small recurring role as a crime scene police officer on the short-lived detective show Harry O. He then landed one-shot episodic 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. By the late 1970s, he got his breakout role as the conniving, cigar-chomping goldbricker Sgt. Luther Rizzo in M*A*S*H. He also appeared as Tom Berenger's sidekick in Rustler's Rhapsody (1985).
He returned to college in 1993, and graduated from Southwest Texas State University, now Texas State, 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.

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