Mooney initially appeared in the sketches "Ask a Black Dude" and "Mooney at the Movies" on Comedy Central's "Chappelle's Show". He later appeared as Negrodamus, an African American version of Nostradamus. As Negrodamus, Mooney ad-libbed the "answers to life's most unsolvable mysteries" such as "Why do white people love Wayne Brady?" (Answer: "Because Wayne Brady makes Bryant Gumbel look like Malcolm X.") Mooney was planning to reprise his role as Negrodamus in the third season of the "Chappelle's Show", before Dave Chappelle left the show due to stress.