Craig grew up in Ohio and began his career as a stand up comic in the late 80s, travelling the country playing comedy clubs and universities. He was a featured comic on "A Night at the Improv" in the early 90s, as well as appearing on the "MTV Comedy Half Hour". He starred in a series of television commercials for "Auto Shade" in addition to several television ads for various radio stations. Craig had an uncredited role as an intern in the movie "Get Shorty" and appeared in several made-for-TV movies before leaving the business in 1996.