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Transamerica, by Duncan Tucker, released in 2005, addresses lesbian, gay, bisexual, transgender and queer- (LGBTQ-) related themes through a transsexual female protagonist, Bree. This article discusses the film as an important step in the direction of representing the complexity of gender, which, by today’s standards, is more generally appreciated. Because of its subject matter, Transamerica is a contentious film, lauded and condemned in mainstream media for how it dealt with and represented transsexual identities. Despite nominations for a number of awards, the film’s portrayal of transsexual identities was largely ignored in academic discourse at the time. I argue here that the film provides insight into the challenges, requirements, concerns, as well as the consequences of gender-fluid expression, which has been recognised in academia for years and has become a more discussed topic in mainstream society, but the manner in which the film examines these insights was overlooked. I do this by contextualising the film in terms of contemporary examples of transgender existence, which have brought the topic to mainstream discourse, and by applying gender theory concepts to the film. I discuss the protagonist’s physical and emotional journey to self-discovery in the context of the road movie trope. I then look into the protagonist’s gender performance, as well as how the protagonist negotiates this performance in the various places she visits while on the journey. I show that the film encourages open and honest discourse about gender identity and expression; the opportunity for this discussion was not taken in the year of the film’s release.