This paper looks at the development of transgender identities in twentieth-century Japan, from their “professional” antecedents in the kabuki theater, through post-war paradigms based in the entertainment world, to recent notions of “amateur” transgenderism and cross-dressing. It is argued that early paradigms of transgenderism centered on occupational categories and that, despite modern understandings that associate transgender performance with homosexuality, the traditional bisexual potential of the transgender body was never completely occluded. In recent years transgender individuals have emerged who, distancing themselves from the entertainment world, have sought to interrogate mainstream notions of “normal” sexual and gender identities-arguing instead for a “gender free” society in which gender expression and sexual orientation are not tied to biological sex.