| Sumario: | Prudence is an essential virtue in a contemporary racial culture marked by the contingencies and the paradoxical in/stability of race and racism. Recurring controversies surrounding racial epithets exemplify this clash between deeply entrenched racial meanings on one hand and shifting conventions on the other. I argue in this essay that racial humor presents a valuable site for understanding and practicing prudential reasoning and performance. Analyzing three episodes from popular texts—The Boondocks, The Daily Show with Jon Stewart, andSouth Park—I illustrate the way racial humor resists prescriptive reasoning and creates possibilities for audiences to practice prudence.
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