The ancient Greeks were, at first glance and among many things, lovers of rather well-defined binaries. Their ideals on gender held that men were men, women were women, and no one, outside the world of mythology, was to cross the boundaries of their assigned gender. However, in practice, such strict divisions often do not hold up; we are able to see vestiges of gender destabilization in several ancient texts, including ancient dramas, which necessitated that male actors assume the garb and personae of female characters. By using Judith Butler’s theory of gender performativity and gender trouble as a framework, this thesis serves as a survey and reexamination of several traditionally masculine characters (including Tiresias, Hippolytus, Dionysus, and Agathon) from both tragic and comic works and seeks to demonstrate that, throughout the course of their appearances, they in some way, shape, or form blur the line between femininity and masculinity.