This essay explores the interrelationship between tragedy and comedy, with specific focus given to the potential that comedy can provide in transforming the most tragic of situations. In building this claim, the very dynamics and distinctions that divide the tragic from the comic are considered in view of the self-negation that the comic posits. That is, while tragedy requires a certain acceptance of the finite, from which destiny and circumstance come to certify the hero’s tragic predicament, in comedy, what succeeds is that which functions through an act of self-negation. This, it is argued, offers a subversive redefining of tragedy, one that proves constitutive of a comic fatalism that does not mourn one’s tragic predicament or fated end, but, instead, fully identifies with our comic predicament. Going beyond the pitfalls of political nicety and moral condemnation, which seek easy gratification or cynical distance, the conclusion examines the conceptual artist, Vanessa Place, and her performance of rape jokes.