G.W. Bailey worked at local theater companies during the mid 1960s until his move to California, sometime in the 1970s. Here he began his work in TV in such shows as "Starsky and Hutch" (1975) and "Charlie's Angels" (1976). He eventually got a movie debut role in a Chuck Norris movie A Force of One (1979) before landing the role of Rizzo in "M*A*S*H" (1972).

In 1993, he went to Southwest Texas State University, graduating in 1994 with a Bachelor's of Fine Arts, Theatre and, for the 1999-2000 school year, he was the Artist in Residence.

While in his 30s, Bailey went prematurely gray, leading to roles of characters much older than his actual age. Although he prefers dramatic acting, his most famous role will always be that of Captain Thaddeus Harris in Police Academy (1984).

Since his goddaughter was diagnosed with leukemia, he has worked voluntarily for the Sunshine Kids Foundation, organizing trips for young cancer sufferers. In 2001, he was announced as the executive director of the foundation.