Before acting, Gilliam was a member of the Coast Guard's boxing team, where he won 201 out of 217 fights. He remained in the boxing world for decades, working as a referee in California.
While working as a fireman for the city of Dallas, Gilliam appeared in the role of "Floyd", the desk clerk, in the film Paper Moon. He then went on to appear in such popular movies as Blazing Saddles and Back to the Future Part III. Performing in Blazing Saddles was difficult for him, since he played a despicable racist who repeatedly hurls racial insults (including "nigger") at the black characters, especially the hero, played by Cleavon Little. Gilliam was so uncomfortable with his use of that slur that he apologized to Little, who had to remind him that it simply was a word in the script and that the racial insults were treated unambiguously negatively since he was playing a villain. Gilliam was also embarrassed by being the main protagonist in the fart scene.
Gilliam also has had roles in movies such as Honeymoon in Vegas, Thunderbolt and Lightfoot, Farewell, My Lovely, Fletch, Gator, Telefon and The Terror Within II. His television appearances include Alice, Charlie's Angels, The A-Team, The Dukes of Hazzard and The Fall Guy, and he appeared as a regular on Evening Shade.

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