This thesis examines Chappelle's Show’s use of racial satire to challenge dominant stereotypes and the effectiveness of that satire as a tool to achieve perspective by incongruity. I use a variation of D’Acci’s circuit of media study model to examine the institutional challenges and limitations on the show due to the context in which it was created, produced, and distributed; to interrogate the strategies employed by the show’s writers/creators to overcome these challenges through the performance of race; and to analyze the audience’s understanding of the use of racial satire through a reception study of the show’s audience. I argue that using satire often has the unintended consequence of crossing the line between “sending up” a behavior and supporting it, essentially becoming that which it is trying to discount, though this is not to say that its intrinsic value is therefore completely negated.