This skit from the second season of Chappelle’s Show (2003-2006) encapsulates many of the pioneering aspects of the show’s treatment of racism in contemporary America. In particular, it represents perhaps the most sustained televisual rumination to date on racial slurs: who can use them, under what conditions, and to what effect. Given the recent uproar about Michael Richard’s racist tirade at the Laugh Factory in Los Angeles and the media fallout that surrounded it, it seems that debates about the politics of racial slurs, particularly the “N” word, have reached a fevered pitch. Ultimately, the Chappelle’s Show skit raises far more questions than it has the capacity to answer, but perhaps this is the most that we can ask of televised comedy or culture in general. As Dave Chappelle explains in his introduction to the skit, it was inspired by the use of the “N” word among young whites, which leads to Chappelle’s question—and the premise of the skit—about using the word to refer to white people. A parody of a 1950s sitcom about a white family named “Niggar,” the skit initially provokes mostly uncomfortable laughter and groans from the audience, until Chappelle appears as a “colored milkman” who revels in calling the family by its last name. The contrast between Chappelle’s ability to use the “N” word in a variety of ways and the inherently racist overtones when used by the white characters provides a nice metaphor for the different connotations of the word that continue to inhere in different racial/language communities. In fact, by the end of the skit, it becomes obvious that the white family is quite aware that their last name doubles as a racist epithet, again underscoring the idea that whites cannot use the “N” word in a nonracist way. There are also subtle undertones throughout the skit about the use of the word to naturalize racist exclusions and violence—such as Chappelle’s observation that Timmy Niggar will “get the best table a Niggar ever got in this restaurant”—and his almost offhand remark, in the midst of guffawing laughter, that “this racism is killing me!” As good as this skit is in terms of bringing to light some of the complex connotations and politics surrounding the “N” word, it does pull some punches. In particular, the decision to locate the skit in a 1950s sitcom family, rather than among contemporary white youth who are a primary fan base for the show (and also the people whom Chappelle is ostensibly most concerned about in the introduction) makes it easy for those fans to escape self-reflection or –critique. In addition, it seems as though the overriding message of the skit is that, regardless of who can’t use the word, Chappelle has asserted his right to do so. Chappelle’s Show is often mischaracterized, even by academics, as a show that travesties everything, resulting in a conflicted cultural politics and cynicism. In fact, as this skit demonstrates, the most consistent targets of Chappelle’s satire are the touchiest aspects of contemporary race relations and racism. Of course, satire is a dangerous gambit; it prevents Chappelle from staking out a clear position on these topics, allowing him only to dredge up a host of anxieties, fears, desires, and debates. Perhaps, however, any desire for politically clear and coherent television—or any other form of cultural expression, for that matter—will always run up against the fact that meaning only inheres in the social uses of culture, in the encounter between socially located texts and viewers. Perhaps Chappelle’s Show and its brand of satirical humor are not any more politically unstable than the PBS documentary Eyes on the Prize. Perhaps, Chappelle’s Show is simply more obvious about its instability.