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This paper draws upon in-depth interviews with 27 drag kings in the Deep South to examine why women choose to perform as men, the range of performance experiences of drag kings and how drag kinging challenges dichotomous ideas about gender outside of the academy. We use these interviews to start a conversation with Halberstam’s (1998) Female Masculinity, which remains the key theory in the study of drag kings. Most importantly, our research points to the importance of context in understanding the drag king culture. We clearly show that in the South the negotiation and performance of masculinity in the form of drag differs starkly from the kings of major metropolitan areas, specifically those addressed by Halberstam. Our findings show that South Carolina drag kings, in general, do not seek to bring a political and thought changing message to audiences as much previous research assumes, rather, South Carolina drag kings turn to drag as a safe and fun outlet for female masculinity and as a place to test the waters of transsexuality. Despite the often individualistic rationales behind drag kinging in South Carolina, we argue that the drag performance still maintains its transformative nature on the surrounding community. Even when drag kings’ purpose is for individual acceptance and fun, they still, by the act of performing various versions of masculinity, challenge the gender order and enable others to engage in political thought and push for change in our society.