In early modern England, as part of a broader interrogation of exemplarity, full-scale works on the Trojan War often subjected the myth’s heroes to humorous scrutiny, whereas the heroines remained surprisingly untouched by comedy. Testifying to the war’s calamities already in antiquity, in the early modern period, the myth’s women acquired a further link to destruction: their sexuality was believed to ‘undo’ men. Embodying different types of suffering, the heroines came to be regarded as inherently tragic. Read against this context, one aspect of William Shakespeare’s and Thomas Heywood’s interventions into the myth appears remarkably defiant. Pursuing divergent aims – in Troilus and Cressida Shakespeare explores the annihilating power of laughter irrespective of gender, in Oenone and Paris and The Iron Age Heywood specifically sets out to rehabilitate female characters – both authors temporarily turn the heroines into objects of comedy. However, if Shakespeare creates a Troy in which mockery is universal, Heywood does not. Thus, although both maintain that laughter against the myth’s heroines ultimately backfires, turning those laughing into comic figures, Heywood, by having the women never resort to mockery, makes them seem more sympathetic, even tragic, whereas their Shakespearean counterparts laugh and suffer laughter’s consequences alongside men.