Comic satirists such as Aristophanes thrive on the tension that arises from their need to ridicule prominent figures of contemporary society and the possibility that this ridicule will cause genuine offense. The history of satire is full of complaints by authors that they work in a dangerous profession, and that their detractors fail to appreciate their high-minded, often explicitly didactic intentions. In such moments, satirists attempt to leave the impression that those who try to repress their freedom to mock and abuse are unwelcome obstacles to their enterprise. It is precisely such allegations of risk and danger, however, that make for effective satire and allow satirists to present themselves as comically “heroic” in the first place. And if satire requires a fraught, antagonistic relationship between author and target, we cannot trust the satirist’s account of the relationship or accept the claim that the alleged oppression is unwelcome. This study begins with such conundra in Aristophanes, and examines comparative evidence from other periods and literary forms, including Homer’s Thersites, Horace, Socrates and Lenny Bruce.