Damien began his career in the Eddie Murphy concert film, Raw. He also got his big break in the film, Malibu's Most Wanted and playing the role of Tec. Damien has written and directed several episodes of the series, My Wife and Kids. Damien and his cousin, Craig also produce the series, The Underground. He also directed the spoof film, Dance Flick. In 2009, Damon and Craig created their own production entertainment company, Second Generation Productions. He also stars in the BET series, Second Generation Wayans.