While committed to the argumentative and reasoned discourse recognizable in the work of contemporary professional philosophers, the actual practice that both Socrates and Diogenes routinely engaged in was in many ways more similar to stand-up and other forms of contemporary performative comedy. This paper analyzes the commonalities between Socrates’s and Diogenes's public philosophizing in Ancient Greece and performative comedy in the contemporary world, and emphasizes the subversive rhetorical efficiency and skeptical significance of public irony for their audiences. The paper begins (...) by exploring the ways in which ancient philosophers relied on irony and humor to promote skepticism and critical thinking, analyzes contemporary comic performances that seem similar, and concludes with reflections on the varieties of philosophical activity and experience. (shrink)