This new study of Menander casts fresh light not only on the techniques of the playwright but also on the literary and historical contexts of the plays. Menander (342/1-292/1 BCE) wrote over a hundred popular comedies, several of which were adapted by Plautus and Terence. Through them, he was a major influence on Shakespeare and Molière. However, his work survived only in excerpts and quotation until some significant texts reappeared in the nineteenth and twentieth centuries on papyrus. The mystery of their loss and rediscovery has raised key questions surrounding the transmission of these and other Greek texts. Theatrical masks from the fourth century BCE discovered on the island of Lipari now also provide important material with which this book examines how the plays were originally performed.A detailed investigation of their historical setting is offered which engages with recent debates on the importance of social status and citizenship in Menander’s plays. The techniques of characterization are also examined, with particular focus on women, slaves and power relationships in his Epitrepontes. It appears that the audience was invited, sometimes subversively, behind the mask of this sophisticated comedy to discover that people do not always conform to literary expectations and social norms.