This thesis presents an exploration of the representation of gender in Virginia Woolf’s Orlando and Jeffrey Eugenides’s Middlesex mainly in light of the theories of Judith Butler. The focus will be on how the two novels challenge the traditional concept of gender and gender categories, and in what ways the novels can give us new perspectives on the concept of gender. The theoretical focus will be on Judith Butler, more precisely her idea of gender as performance, and her deconstructionist approach to identity categories. I will present Butler’s proposal for a “new feminist genealogy,” and through my investigation of the representation of gender in Orlando and Middlesex I will show how both novels take on a “Butlerian” understanding of the concept of gender. By looking at various issues related to gender explored in the two novels, and pointing to similarities and differences between the two works, I hope to show how the protagonists, Orlando and Cal/lie, break down and transcend the fraught categories of male and female, thus disrupting the traditional gender norms and conventions, showing them to be socially and culturally constructed. Judith Butler’s hope is for every human being to be acknowledged as a subject, no matter which gender and/or sexual identity he or she has, and my aim is consequently to present how Orlando and Middlesex, through their representation of gender, open up for a greater understanding and broader acceptance for every individual.