Although he has appeared in many dramatic roles, he may be best remembered for his "crusty" comedic characters such as Staff Sergeant Luther Rizzo in M*A*S*H (TV series 1979–1983); Lieutenant/Captain Thaddeus Harris in the Police Academy films (1984–1994), and Captain Felix Maxwell in Mannequin (1987).

Bailey was born in Port Arthur, Texas, where he went to Thomas Jefferson High School with Janis Joplin and Jimmy Johnson.

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.

From 2001 to 2019, Bailey served as the executive director of the Sunshine Kids Foundation,[4] which provides trips and activities for hundreds of young cancer patients annually.