In this thesis project, I investigate the drama of Perry and introduce his dramaturgy into the academic landscape. As the critical discourse is shifting towards the realm of popular culture, we must begin to locate several discourses at work in the drama of quite possibly the most popular, visible, and financially successful African American playwright of the twenty-first century, if not of all time. Drawing on gender and queer theory, I offer a theoretical discussion about subversive and non-subversive drag acts, and I question the degree to which Perry appropriates drag in a politically liberating or constraining manner. Moreover, I examine the gender and sexual politics in Madea’s Family Reunion to illustrate the ways in which I read Perry as offering a very conflicted dialectic between activist aspirations and oppressive tendencies, particularly in regard to questions of safe feminist spaces, motherhood, female self-sufficiency, female self-definition, domestic violence, and homosexuality.