Teen Shakespeare films have largely been dismissed as films which “dumb down” Shakespeare’s original texts and which are marketed in a manipulative way in order to sell teens fantasies that appeal to them. Among the most popular and recognizable actresses of this genre is Julia Stiles, known for her leading roles in 10 Things I Hate About You, O, and Hamlet. Several scholars have critiqued Stiles’s films for the ways that they depict feminism and American teen girlhood. In this thesis, I argue that Stiles’s films present a spectrum of, an admittedly limited, feminism that becomes increasingly more progressive. By exploring Stiles’s portrayal of feminism in these films, the hope is to move away from the idea of teen Shakespeare films as merely dumbed down versions of the plays and to, instead, move towards an understanding of the political and social role of this generic category.