The paradox of tragic pleasure has inspired discussion from ancient Greece and on to our days. Aristotle and Aeschylus in ancient Greece, Thomas Aquinas and Dante Alighieri in medieval France and Italy, and Thomas Hobbes and Jeremy Bentham in early-modern England, discussed the same basic problem – how can the consumption of pain generate pleasure? – with respect to practices that were culturally intelligible as punishment to contemporary audiences: the classical tragedies, afterworldly punishments, and public executions. The chapter revisits the philosophical discussion in each period to account for the spectators’ enjoyment. The world-making quality of punishment is assumed to be the key to the paradox. It is necessary to look beyond the salient pain and suffering. The Attic tragedy, the medieval visions of divine justice and the early-modern executions are seen to enact a world in the dimensions of justice and order, along with a shared existential predicament of the audience, which was tragic in the original sense of being faced with impossible options. The spectators were included in the enacted world and were recognized by each other as fully part of it, as male citizens of Athens, as ordinary members of the Christian community, or as subjects of the monarch.