Concepts of mental health and normality cannot be understood apart from cultural norms and values. The most significant of cultural constructions that shape our view of madness is gender. Madness has been perceived for centuries metaphorically and symbolically as a feminine illness and continues to be gendered into the twenty-first century. Works of art and literature and psychiatric medicine influence each other as well as our understanding and perception of mental illness. Throughout history, images of mental illness in women send the message that women are weak, dangerous, and require containment. What are the cultural links between femininity and insanity, and how are they represented? Through the lenses of disciplines such as theatre criticism, feminist theory, and psychiatry, this thesis examines the history of madness as a gendered concept and its depictions in art and literature. Additionally, it will explore the representation of female madness in contemporary dramatic literature as compared to the medical model used during the era in which it was written as well as the social and cultural conditions and expectations of the period. The three plays under consideration are: Long Day’s Journey Into Night, written in 1941 by Eugene O’Neill; Fefu and Her Friends, written in 1977 by Maria Irene Fornés; and Next to Normal, produced on Broadway in its current form in 2009 and written and scored by Brian Yorkey and Tom Kitts. None of these plays tell a tidy story with a straightforward ending. In none do treatment facilities offer refuge or health professionals offer answers. Struggling characters resort to drug abuse, fall prey to internalization, or leave treatment all together, having been subjected to enough victimization. The relationship between patient and physician is depicted to be, at best, ambivalent. The themes in these plays illuminate women’s mental illness as an extensive problem with many contributing factors, and the origins of which are quite complex.