Following up on Xenophanes’s and Heraclitus’s uses of humor, the Cynic philosopher Diogenes of Sinope and the skeptic Timon of Phlius made humor a central element of their philosophical practice. Diogenes’s invectives aimed at awakening his listeners to their own reason and overcoming inconsistencies between their rational commitments and their actual behavior. As to Timon, his caustic parodies were directed against all dogmatic philosophers: by laughing at these philosophers, we readers are supposed to share the typically skeptical commitment to “suspension of judgment,” which leads to ataraxia, or the “absence of trouble.”