This dissertation features the stories of drag king performers. Through life story interviews coupled with participant observations, and informed by gender performance, poststructuralist, and psychoanalytic theories, this project examines the ways in which drag performers construct, take up and perform multiple subjectivities and how they benefit from multiple knowledges in their learnings and unlearnings. Through an examination of the creation and circulation of these drag king pedagogies, I suggest ways in which drag performers create and sustain gendered knowledge, while navigating difference and working with multiple discourses of identity, oppression, and power in a socially and economically diverse city. Participants’ perceptions of their gender identities point to the ways in which identity categories are insufficient. Each participant uses an existing identity label (e.g., transgender, tranny, boi) or a combination of existing labels, to understand their gender identities, even as their narratives point to the failures of fixed categories. It is my contention that the narratives of these particular performers highlight the multiplicity of all selves, and the ways in which all learnings and unlearnings are fragmented. Thus, drag king narratives have significant pedagogical value in examining the relationships between subjectivities and knowledge.