This study examines how cross-dressers and transsexuals are represented in three different film genres - comedies, thrillers and mixed genre productions - focussing on examples such as Some Like It Hot, Tootsie, Mrs Doubtfire, Victor/Victoria, Psycho, Dressed to Kill, Silence of the Lambs,The Crying Game and Boys Don't Cry. It also includes a chapter on 'shemale' Internet pornography. Relying on psychoanalytic, queer and other post-modern theories, the author describes the influence of these cultural representations in the context of an increasingly, problematic distinction between the worlds of the imagination and reality, demonstrating the interdependency of our perceptions of transgender and its culturally constructed images.