This thesis foregrounds literary analysis of hypermobility with an overview of the historic medicalization of hypermobility, or an excessive range of motion, with attention to how the politics of pathologizing movement enforces normative standards for permissible ranges of physical and social mobility. It provides an overview of how hypermobility became a medicalized diagnosis, tracing from Hippocrates to contemporary diagnostic guidelines. To subvert the medical model and reclaim the word "hypermobility," this thesis examines cultural instances of hypermobility in both contemporary street dance and gothic short fiction. It details the importance of bone-breaking dance as a new dance form that dramatizes the freedom and mobility of Black Americans through the performance of joint dislocations as metaphors for escape from bondage and enslavement. Turning to the gothic short story, this thesis explores how figurative and supernatural hypermobility in "The Cold Embrace" (1860) by Mary Elizabeth Braddon illustrates the characters' gendered relationships to movement and autonomy. When examined as a whole, these transatlantic examples of short stories and performances elucidate how the performance of hypermobility reflects and protests constraints of gendered and racialized oppression.