Humor lends itself as a convenient tool to address sensitive issues such as race. Since 1997, the TV series South Park with its brash satire and rampant irony has been a prime example of how such issues are negotiated in American popular culture. However, the utilization of highly rhetorical devices such as satire or irony has divided scholars on whether the series promotes or stifles social discourse on race and ethnicity. In this article, I examine the episode “With Apologies to Jesse Jackson” (2007), focusing on how white feelings of anxiety are portrayed in this episode that is permeated by racial tension. The particular representation wavers between a social critique of the state of race relations in the United States and a portrayal of white anxiety as hindering open discourse on the topic. Ultimately, the article demonstrates that the scenes containing elements of white anxiety are portrayed in such a way as to critique the current dysfunctional state of race relations in the United States, urging viewers to critically consider issues of race rather than to inhibit such discourse.