In 1990, Damon and his brother Keenen co-created the comedy sketch show “In Living Color,” which ran on the Fox network until 1994. He had a variety of parts on the show as well, which earned him four Emmy nominations.
After that, he created and produced the Fox drama series “413 Hope St.” (1997–98). His next significant role came in 1998 when he played the title role in the Fox comedy series “Damon.” He then played Pierre Delacroix in the satirical comedy-drama film “Bamboozled” (2000), which was directed by Spike Lee.