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Laughter is one of the most difficult and intriguing historical subjects, one that defies firm conclusion or systematization. Beginning with Dion Cassius’s first-person account of laughter in the Colosseum in 192 CE, this article explores some of the heuristic challenges of writing about the laughter of the past—particularly that of classical antiquity. It attempts to undermine some of the false certainties that surround the idea of a “classical theory of laughter” (which originated during the Renaissance) and argues that ideas about laughter in ancient Greece and Rome were much more diverse than one usually imagines. Important patterns in the discursive use of laughter in ancient Rome can nonetheless be observed. This article also examines the way laughter was used to mediate political power and autocracy in addition to how laughter operated on the boundary between animals and humans. It concludes with a reflection on the extent to which we can still share in the laughter of the Romans and under what conditions.