This thesis is an interdisciplinary study of the largely neglected relationship between madness and masculinity based on three American literary works written during different periods of the twentieth century. The study utilizes literary, social, and medical research in order to provide a holistic view of madness and masculinity as two social constructs that interact with and are contingent on each other. In Sherwood Anderson’s “Hands,” Ken Kesey’s One Flew Over the Cuckoo’s Nest, and David Foster Wallace’s Infinite Jest, madness and masculinity are depicted as mutually dependent concepts that reflect the social norms and cultural beliefs prevalent in society. Although in literary studies, madness has popularly been considered and examined as a female malady, Anderson’s, Kesey’s, and Wallace’s protagonists are male characters whose experience of madness illuminates the damaging effects of gender dualism on the identity of men who struggle to conform to socially defined norms. My aim in outlining the literary history of madness and masculinity within the limits of a specific time span is to show that the dualistic gender ideology of Western culture, as well as attempts both to enforce and subdue gender dualism, has had a significant impact on the definitions of and social attitude towards madness throughout the twentieth century.