The teen movie Pretty in Pink presents a gendered dichotomy that exists between females as musical connoisseurs and males as emotional performers that is far from rare within the teen movie genre of the mid-1980’s to early 2000’s. These recurring tropes raise important questions about the teen movie genre and its use of popular music. How and why does the teen movie divide its musical scores along gendered lines? What do these musical differences tell us about the contrast between female and male adolescence? What is the significance of the “Rebel Girl” within the history of the teen movie, and how are we to interpret the teen boy who bursts into song onscreen? This article’s goal is to dig more deeply into these questions by viewing the teen movies soundtrack through the lenses of gender identity, musical genre, and the cinematic conventions of popular song scoring.