Though he would return to higher education nearly three decades later, Texas native G.W. Bailey left college and spent the mid-'60s working at local theater companies. Determined to establish an acting career for himself, a young Bailey moved to California in the 1970s and worked in a variety of settings. From appearances on television's Starsky and Hutch and Charlie's Angels to stage productions of Shakespearian classics, Bailey, despite his lack of professional experience, proved a surprisingly versatile actor. He did not, however, attain significant mainstream recognition until 1981, when he was cast as pool-hall con artist Private Rizzo in CBS's long-running series M*A*S*H. The exposure led to five large supporting roles on a variety of feature-length television dramas, and ultimately, a very different type of performance all together: that of the imposing yet incompetent Lieutenant Harris in the lowbrow cop comedy Police Academy (1984). His Police Academy role was reprised as sequels were churned out in rapid succession, and he was cast as a similarly inept authority figure in 1987's Mannequin.
Though the 1980s found Bailey immersed in fairly unmemorable film roles (mainly comedies and dark thrillers), he was able to forge a more than respectable resumé in the realm of television movies, including the popular Murder in Texas (NBC, 1981), On Our Way (CBS, 1985), Spy Games (ABC, 1991), and Dead Before Dawn (ABC, 1993). His television roles offered a G.W. Bailey quite unlike Lieutenant Harris, and he was able to develop a following and a steady reputation as a supporting actor. Eventually, he was able to add "college graduate" to his list of accomplishments, as his mid-'90s stint at Southwest Texas State University proved successful as well. In 2004, Bailey lent his vocal chords to Disney's animated musical Western Home on the Range.
He was cast as Lt. Provenza on The Closer, a show that would be for a time the highest rated scripted program on basic cable, and he would stay on the show for its entire run.