The present paper poses the question of the different ways in which madness is laughed at—or with—in Attic Tragedy and in Old Comedy. What is the significance of each kind of “mad laughter”? I shall identify fundamental differences, related to the different kinds of character, mental aberration and dramatic conflict presented in each genre, and more broadly to the dramatic structure and function of each. A first distinction can be made between laughter at madness, which we see especially in tragedy, and laughter with, or embracing of, madness, which we experience in comedy. The second distinction is between two profoundly different understandings of and approaches to mental aberration: as intensely individual, “medical,” affliction (in tragedy) on the one hand or as essentially a social problem (or sometimes blessing), with social consequences and, in some cases, social solutions (in comedy) on the other. In the process, we shall also consider the significance—and some of the complexities—of the “curse versus blessing” analysis; questions as to who directs the “mad laughter” and who are its audience(s) (the original audience of the play; onstage characters, mortal and divine; the modern reader); and some relevant features of the visual and physical depiction of madness—in particular the use of mask—in both genres.