This chapter opens a perspective onto the more theoretical or conceptual side of humorous discourse in twelfth-century Byzantium by exploring the reflections on ridicule and comedy in Homeric poetry in the commentaries by Eustathios of Thessalonike. Eustathios addresses the social aspects of ridicule, as well as its rhetorical dynamics and its role in narrative. In his view, Homer uses comic elements to counterbalance the gloominess of the Iliad’s war narrative, as a good rhetor should do. Flyting has the same function: even if the addressees in the narrative are stung by such insults, Homer’s primary narratees are expected to be amused by the often humorous verbal abuse. Eustathios repeatedly points to the moral tensions inherent in ridicule and laughter; as the consummate orator, however, Homer always finds a way to keep his dignity intact. Throughout his commentaries, Eustathios offers his target audience of prose writers numerous examples of how to adopt and adapt Homer’s words in order to ridicule certain bodily defects, excessive behaviours or less-than-perfect intellectual skills. Such comments shed light on what was worthy of mockery in the mind of a Byzantine audience and show that it was expected of urbane rhetors to use ridicule in their writings.