In considering Plato’s position on humor, we are faced with an apparent paradox. There is evidence that Plato thought deeply about humor and recognized its value––Plato’s writings and Socrates’s ironic disposition testify to his comedic sensitivity––but Plato’s explicit remarks on the subjects of humor and comedy are largely negative (e.g. Laws 934d-936c; Apology 18d, 19c; Philebus 48a-50c; cf. Morreall 1983: 4-5). This paper aims first to reconstruct his view on the topics of humor and comedy, and secondly to examine this apparent paradox in light of that reconstruction. I argue first that Plato’s discussion of comedy in the Philebus is intended to apply narrowly to the case of malicious comedy. I’ll then argue that, understood in light of the broader context of the Philebus, Plato’s account is possessed of resources to explain both why humor is a valuable part of the good life, and why, for some individuals, exposure to humor brings only deleterious effects and should not be indulged.