Several years ago in a lecture called ‘How the Heroes Talk’, T.A. Shippey enumerated tacit or understood speech patterns that determined whether exchanges between Germanic heroes should lead to peace or battle. In subsequent published essays he has elaborated on these patterns based on Paul Grice's rules of conversational logic. These discussions may also help explain how the heroes (and their poets) joke, as exhibited particularly in Beowulf. In the medieval Germanic world formal exchanges between heroes (or among gods) may use ostensible humor as a way of establishing dominance, and while such ‘wars of words’ may lead to violence, they simultaneously exhibit what E.V. Gordon called, referring to Old Norse literature, the ‘cheerfulness of the man who feels that he is a master of life’ and a moral/practical warning to avoid placing oneself in danger of vengeance. For example, in a flyting, while that cheerfulness might increase one's chances of survival, the hero must use insults prudently, to avoid placing himself in much greater danger later and to situate himself in a position so he may accomplish his goals in the present. The humor in Beowulf, though, goes beyond flytings to include irony and wordplay. Determining the humor of a culture from a thousand years ago requires a degree of brazen guesswork, but analysis of passages that at least present the potential for humor offers some interpretive options that we may consider against the heroic backdrop of grotesque monsters and inconsistent courage.