A thesis that explores the broad appeal of narratives with adolescent protagonists across a variety of media, including literature, film, and video games. An analysis of key texts within their historical contexts reveals affinities between disparate genres and strong connections between fiction and the discourse of adolescence in psychology, anthropology, and sociology. Adolescence narratives illuminate both the transgressive boundaries of a given culture and the normative center, and make explicit what is usually considered natural or implicit. To discover the roots of contemporary adolescence narratives, prototypes for the picaresque novel, the school story, and the Bildungsroman are examined, and each are shown to contain narrative conventions that survive in recent works. A contemporary case study looks at the trilogy of female coming of age films by Sofia Coppola to show how they embody the ambiguities and contradictions of third wave feminism. Finally, the author explores the affinity between video games and adolescence, the implications of translating literary genres into an interactive medium, and uses examples from both science fiction literature and recent games to theorize how games might better address the themes of adolescence in both story and play mechanics.