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This dissertation examines how American dramatists in the United States have constructed performances of black masculinity. The African American plays analyzed in this dissertation represent black men wresting their voices from the negative depiction by white artists and combating negative stereotyping. Performance often becomes and is used as a prison that captures and fixes representation beyond the historical moment, instead of a liberatory medium for social change. Likewise, racial discourses often collapse faulty historical narratives. This study on the performances of Black male masculinity in theatrical contexts explains how late twentieth century playwrights imagined, created and replicated black men. These texts and contexts not only fix representation in a medium that is replicable, but they also capture the social impressions about Black men, which dominate the popular imagination as well as academic theorizing. This study identifies common themes that explain (1) how artists create imagery that communicates their lived experience, and (2) how artists exemplify specific challenges of racial, gender and national performances in contemporary theatre. With the demise of chattel slavery in the United States, Black men have had to define physically their place in the country. Is it better to stay on the land and transform a history of bondage into a positive tradition or flee from the physical place of bondage in hopes of a better world? Chapter 2 examines how Samm-Art Williams orchestrates one man’s journey through the geography of palatial identity. Most contemporary African American dramatists depict either poor or working class black men. Chapter 3 will examine the construction of black masculinity by black women. The selected plays demonstrate how Black men negotiate relationships with mothers and female partners in addition to friendship with other men. Chapter 4 seeks to connect the preeminent gay black theorist with the cultural nationalism of the Black Arts Movement. Chapter 5 will examine Black men in public spaces. Tom Cole’s Medal of Honor Rag demonstrates the internal and external policing of the psyche that many Black men face. The play reflects varied subject positions but they provide crucial commentary on cultural practice in each society.