Damon Wayans
Wayans plays the TV writer of a comedy-variety show and brings to the role his experience as a writer and performer on the legendary Fox Network variety show In Living Color. The show that Delacroix creates with the intention of being so racially charged as to be impossible to air does contain some elements of the satirical perspective of In Living Color which pushed the boundaries of exposing the racist overtones of what much of white American had long viewed as funny about African-American culture and history.
Michael Rapaport
Rapaport gives the kind of performance that gets actors assaulted. His character is distinctly unpleasant and unlikable—despite being hilarious—and Rapaport brings him to such full life that it is easy to imagine some disturbed individual confusing the character and the player. Part of the design of Dunwitty is to make him accessible in order to reveal that even the most painfully unaware racists can be engaging on a certain level and Rapaport nails that essential element to the point that some viewers will actually be forced to face their own level of racism through association.
Savion Glover
Glover was thrust into media spotlight with his roles as actor and choreographer of Broadway hit "Bring in 'da Noise, Bring in 'da Funk” just four years earlier. His role in Bamboozled was his first starring in a feature film and remains his last to date.
Jada Pinkett-Smith
Pinkett-Smith received an Image Awards nomination for Best Actress for her role as the voice of reason and (for the most part) calm in the film. Of special note is that though her character wears glasses at work, she does not seem to suffer any vision problems whenever she is show not wearing them and so may represent a symbolic statement about appearances versus reality.
Tommy Davidson
Davidson is another veteran from the Fox variety series In Living Color. The tie between that show and the fictional variety show in the film cannot be underestimated. The real life show was defiant in its attempt to reconstitute longstanding African-American comedy tropes in a way that revealed the underlying racism and taken to its extremity, the show might well have become an actual satirical version of the show within the show.
Mos Def/Yasiin Bey
Credited at the time as Mos Def, Yasiin Bey was a rapper who had been acting since the late 80’s. His appearance in Bamboozled seems to have supercharged his career, however, as shortly afterward he appeared in a number of high profile films such as Monster’s Ball and The Italian Job before achieving leading man status in The Hitchhiker’s Guide to the Galaxy and Be Kind Rewind. Just as quickly, his rise to star status seemed to dissipate as he turned his attention to other projects.
