This thesis navigates through the discourse surrounding Caitlyn Jenner and Rachel Doležal as public figures who self-identified as members of societally defined groups they were not born into. While Caitlyn Jenner, a transgender woman, was generally supported in her transition, Rachel Doležal’s authenticity was questioned for positioning herself within the Black community, and deceiving others about her racial classification. This work aims to examine the manner in which rhetorical communicative decisions of authenticity regarding race and gender are made and play a role in defining and stratifying the hegemonic hierarchies of identity that exist within our current sociocultural climate. Despite the fundamental similarities between the identity constructions of both individuals, their narratives are presented to us in opposition, which lead to questions of identity construction, expression, and the societal structures that exist to keep identity hierarchies in place. This analysis dissects the fluidity of gender and compares it to the immobility of racial identity constructs as functions of performance, discourse, and episteme in contemporary discourse.