He began playing small roles in TV movies such as "The Runaway Barge" (NBC, 1975), "The Summer of My German Soldier" (NBC, 1978) and "Fog" (CBS, 1981), but recognition didn't come until Bailey was cast as Private Rizzo, a pool-hall con man, in the 1981-1983 seasons of the hit sitcom "M*A*S*H*" (CBS, 1972-1983). This exposure won Bailey his first of five dramatic TV movies directed by Roger Young. His role in "Bitter Harvest" (NBC, 1981) was small, but he went on to play larger roles in "Love and Lies" (ABC, 1990), "Held Hostage: The Sis and Jerry Levin Story" (ABC, 1991), "Doublecrossed" (HBO, 1991), and as one of the militia fugitives in "Ruby Ridge: An American Tragedy" (CBS, 1996).
Bailey began another, very different, long-term relationship in 1984, when he played the hard-nosed Lt. Harris in the lowbrow hit "Police Academy." He went on to recreate this role in "Police Academy" sequels number 4 through 7, which grew more lowbrow and less successful by the year: "Citizens on Patrol" (1987), "Assignment Miami Beach" (1988), "City Under Siege" (1989) and "Mission to Moscow" (1994). The dubious upshot of this was supporting roles in more thudding comedies, such as the goofy Western parody "Rustler's Rhapsody" (1985), "Short Circuit" (1986) and "Mannequin" and the Whoopi Goldberg vehicle "Burglar" (both 1987). He also appeared in a handful of dark thrillers ("Warning Sign," 1985; "Write to Kill," 1991).
But Bailey had much better luck and a broader canvas for his talents on TV. He played supporting roles of varying size in a huge number of TV movies and mini-series apart from his work with Roger Young, many of them dramas. The most popular included "Murder in Texas" (NBC, 1981), as a Mayor in "On Our Way" (CBS, 1985), a soldier in the epic "War and Remembrance" (ABC, 1988-1989), the agency head in "Spy Games" (ABC, 1991), and an FBI man in "Dead Before Dawn" (ABC, 1993). These roles were all a far cry from "Police Academy."
Series TV has also proven rewarding to Bailey, to a lesser extent. The pilots "There Goes the Neighborhood" (NBC, 1983), "The Earthlings" (ABC, 1984) and "True Stories" (Fox, 1993) failed to take off. But he did have continuing roles as a psychiatrist during the 1981-1982 seasons of "St. Elsewhere" (NBC) and as the anxious news director of a TV station in the sitcom "Goodnight Beantown" (CBS, 1983-1984). He was later cast as the father on "The Jeff Foxworthy Show" (NBC, 1996-97), a character Bailey has described as "a middle aged Lothario." Bailey also returned to college in the mid-90s, finally earning his degree and signing on as artist-in-resident at his new alma mater, Southwest Texas State University.