Cabaret star and television personality Carlotta, a transsexual woman whose fame has endured for more than half a century, is arguably the most prominent transgender celebrity in Australia. This article takes screen representations of Carlotta as its focus to investigate the mainstream media’s treatment of a celebrity who embodies a traditionally marginalised subject position. First examining depictions of Carlotta from the 1960s and 1970s, and then looking to more contemporary examples from the 1990s and 2000s, the paper traces the evolution of Carlotta’s representation on Australian screens. The article considers the problematic elements apparent in individual screens texts, but also the ways in which these texts enable Carlotta to challenge the rigidity and ‘taken for granted-ness’ of the sex-gender system. The paper does so in consideration of Sandy Stone’s proposal of visibly intertextual transsexualism, Kate Bornstein’s advocacy of ambiguous and fluid transsexualism, and Riki Anne Wilchins’s assertions that transsexualism is a practice of transformation. As a transsexual celebrity, Carlotta’s appearances in film and television give mainstream Australian audiences the opportunity to engage ‘safely’ but constructively with a transgender person, thus informing real-world attitudes towards transgenderism, and her public presence affirmatively reflects transgender experiences. Through these screen representations, Carlotta illustrates progressive possibilities of transsexual gender embodiment