Gendered "realness" and its social and political effects are at the heart of transgender issues. "Realness" operates both as a structure for trans intelligibility and its process of containment, for its representation and its erasure. Power works through the concept of gendered "realness" in ways that force trans people to evoke a core, stable gender identity in order to prove their social and legal legitimacy; at the same time, the slippery nature of "realness," its cultural power, and its ability to escape the parameters of determinacy, allow it to be harnessed in social, legal and institutional contexts in ways that undermine trans identities. By looking at what I refer to as "the politics of the real" I analyze gendered "realness" as an operation of power which circulates throughout United States having particular concrete, material effects for trans people. Through an analysis of transgender representation in photography, popular film, feminist theory, and legal cases, I explore the paradoxical nature of "realness" and its function in both dominant culture and transgender communities. As a driving concept for transgender representation and as a strategy for resistance, "realness" needs to be analyzed and evaluated.