Appearing both in his 1996 HBO special Bring the Pain and his 1997 stand-up album Roll with the New, American comedian Chris Rock’s routine “N-word versus Black People” has brought fame and courted controversy. After comparing his work in Entertainment Weekly to comic classics like Redd Foxx, Steve Martin, and Richard Pryor, Daniel Fierman called it “Chris Rock’s groundbreaking star-making […] routine” (Fierman). Writing in Variety, Ray Richmond stated that the routine transformed “Rock from a respected but largely unmarketed standup to the front burner of comedy’s future” (Richmond). In response to the fact that in the approximately six minutes that the routine lasts, Rock uses the “n-word” at least 34 times (my count) multiple people, such as Justin Driver, have expressed criticism writing that “Chris is attempting to shuck, jive, grin, and bulge his eyes all the way back to the days of minstrelsy. His act often legitimizes white racists’ views of the world” (quoted in Leung). Such reproach seems to have connected with the comedian who, when discussing the routine on 60 Minutes, stated “I’ve never done that joke again, ever, and I probably never will. ‘Cause some people who were racist thought they had the license to say the n-word. So, I’m done with that routine” (quoted in Leung). Rock’s feelings understood, the routine could also be argued as important in expanding the boundaries of racial dialogue in the United States as well as discussion about the need for self-criticism in the Afro-American community. Perhaps a testament to this is the fact that candidate-Barack Obama referenced the routine in a Father’s Day speech he gave in 2008: “Chris Rock had a routine. He said some—too many of our men, they're proud, they brag about doing things they're supposed to do. They say ‘Well, I- I'm not in jail.’ Well you're not supposed to be in jail!” (quoted in Baumann). Rock’s humor is the kind the pushes the boundaries of civil conversation. Watching his performance, it is possible to see entranced audience members laugh quickly and then check themselves, looking around to make sure those sitting nearby have also shared in the mirth. It is almost as if people want to agree with his words, but they know that the chosen rhetoric is inappropriate and therefore have to make sure that laughing about such things is socially acceptable. In the video of this routine it is possible to actually see the country’s dialogue about race expanding. This is the power of dark humor and Rock knows it is dangerous. When asked why it took so long for someone to say what he did, Rock responded by directly wading into racial politics, stating “[b]ecause it is threatening to white people” (quoted in Brennun). What is the trick? Why is he able to say successfully what others have not? Rock expresses confidence in the power of his medium: “Comedy’s special […] If my stuff wasn’t funny you wouldn’t be here right now. The exact same things have been said in serious ways, and nobody cares. It’s all about the jokes at the end of the day” (quoted in Brennun). Humor is indeed special, capable of breaking the ice and, through laughter, facilitating discussion of subjects that would otherwise be uncomfortable.