Teens are one of the largest markets for movies. Representations of teenagers in film have the potential to powerfully impact their sense of self and society (Elbaba, 2019, para. 17), yet mainstream films in the high school genre have typically recycled the same narrow teen stereotypes and narratives since the 1980s (Shary, 2014, p. 19). However, film critics, social commentators, and social media reactions lauded a notable exception in Booksmart (Wilde, 2019). The research reported in this thesis was an analysis of the narrative arc and character tropes in Booksmart intended to explore how these differed from those typical in this genre. The analysis identified several ways that Booksmart deviated from traditional gendered forms in the transformational elements of the narrative and in the strategic use of familiar tropes to disrupt stereotypes. Ultimately, while it is limited in some ways (e.g., racial diversity), Booksmart does include more multidimensional characters and contemporary youth issues (deconstructing stereotypes, beauty standards, etc.) compared to most mainstream films in the teen American high school film genre.