Midway through the 1986 teen movie Pretty in Pink comes a strikingly memorable scene. The film's main character, Andie (Molly Ringwald), sits nonchalantly in the local record store where she works. Adorned with posters of mid-1980s post-punk groups like New Order and The Smiths, the store represents Andie's strong alternative music identity. In this particular scene, however, Andie's boss places a recording of Otis Redding's Try a Little Tenderness on the turntable, instantly transforming the mood. From out of nowhere, Andie's best friend, the overly-dramatic Duckie (Jon Cryer), bursts into the store and for the next two minutes proceeds to lip sync, dance, and gyrate his way through the climactic second half of Redding's 1966 soul classic. It is an enraptured, exuberant performance, almost as if he is physically possessed by the music. Andie, the object of Duckie's affections, however, is clearly unimpressed. Soon after his musical display, the deflated Duckie sadly learns that Andie's romantic longings lie elsewhere. His thinly masked musical cry for affection and tenderness has been in vain. As unique and unforgettable as this scene is, the gendered dichotomy that it presents between females as musical connoisseurs and males as emotional performers is far from rare within the teen movie genre of the mid-1980s to early 2000s. From Some Kind of Wonderful (1987) to 10 Things I Hate About You (1999) and Juno (2007), again and again we see female characters positioned as social outsiders via their devotion to alternative musical tastes. Likewise, in films as varied as American Pie (1999), She's All That (1999) and Napoleon Dynamite (2004), teenage boys repeatedly assume the roles of dynamic performers. By breaking out into song, and often dance, adolescent males attempt to overcome social challenges. 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, (2) and how are we to interpret the teen boy who bursts into song onscreen? My goal in this article is to dig more deeply into these questions by viewing the teen movie's soundtrack through the lenses of gender identity, musical genre, and the cinematic conventions of popular song scoring. As a coming of age film, the teen movie deals specifically with the gendered rites of passage that mark the symbolic transition from adolescence to adulthood. Music in these films can thus help underscore a character's social transformation. Regardless of how the music guides our understanding of these characters, popular song functions differently for boys than for girls. If we commonly find boys performing their gender in spontaneous moments of public music spectacle--what I call a form of karaoke masculinity--girls are more likely to maintain a consistent outsider musical identity. A female character like the rebel girl is granted a stability through her musical connoisseurship, only to meet with various threats and tests as she navigates her way through the teenager's turbulent social world. I begin this exploration by presenting a brief historical overview of the teen movie genre's birth in the mid-1950s and its musical scoring practices. From there I describe the changes that occurred in the early 1980s which ultimately served to redefine the teen movie. Specifically, this new wave of teen movies began to portray adolescence in a way that resembles anthropologist Victor Turner's description of the liminal journey, a socially defined process marked by rites of passage towards adulthood. Director and producer John Hughes is often credited with popularizing this narrative story structure, and from his very first teen movie feature, Sixteen Candles (1984), he deployed music as a way of enhancing character development, particularly along lines of gender, age, taste, and performance. …