Race complicates social interactions and stymies citizens; many have trouble even discussing problems of race. Consequently, race continues to present problems for civic judgment and action in United States' culture. While racial comedy seems like an unusual path toward social justice and change, in this dissertation I argue that careful consideration of comic discourses on race presents an entree to the problems of racial judgment. Racial comedy is an inventive resource that models skills and attitudes necessary to better respond to the complexities and contingencies of racialized culture. The dissertation focuses on the role of racial comedy as a guide toward "democratic style," a repertoire of conventions necessary for prudent judgment and just interactions. Through the theoretical lenses of critical, rhetorical education and critical pedagogy, I analyze comic texts and public discourse about comedy ranging from Richard Pryor to Margaret Cho to South Park. I argue that comedy cultivates both a critical reasoning capacity and sensitivity to action in pluralistic settings necessary to navigate the complexities and uncertainties of race in public culture. I also suggest that comedy models a humanizing consciousness that enables citizens to act in pluralistic communities with humility and forgiveness. These skills and orientations, modeled in racial comedy, have the potential to cultivate wise, responsible judgments in response to ongoing racial injustice.