John Hughes is nearly synonymous with the teen film, having written, produced, and/or directed several of the 1980s’ most successful and acclaimed films of the genre. However, the less recognized Amy Heckerling deserves reappraisal as an important teen film director, with three key efforts in the genre in three separate decades. Lesley Speed writes, “Heckerling's career also reflects on the role of contemporary female film directors in expanding teen film and low comedy beyond their traditional masculine preoccupations.” Indeed, with Fast Times at Ridgemont High (1982), Clueless (1995), and Loser (2000), Heckerling mixes comedy and drama as her young protagonists find themselves out of their depth, and taking on adult situations, often without knowing what they are doing. Stacy (Jennifer Jason Leigh) in Fast Times, Cher (Alicia Silverstone) in Clueless, and Dora (Mena Suvari) in Loser are trying to be adults; they think of themselves as adults, and all learn various lessons through their misadventures. These characters ultimately discover that adulthood is about asserting one's agency, and making informed choices regardless of society's proscriptions or peer pressures. Heckerling's teen films prominently express this lesson on adulthood through the spheres of sexuality and gender roles. In each of her teen films, Heckerling argues that teenage women should respect and educate themselves in sexual matters, and follow a path that makes them most happy. Her films also point out the absurdity of patriarchal demands upon young men to fulfill traditional gender roles, specifically the role of sexual conqueror. In doing so, Heckerling's works achieve nuanced representations of teens that are more than fodder for comedy or cautionary tales as they skillfully contemplate the transition from childhood to adulthood.

Sex and the negotiation of gender roles are key aspects of adolescent and young adult maturation. Unlike many teen films of the 1980s and 1990s, which handled sex in terms of polarities between, as Timothy Shary puts it, the “frivolously unenlightened” and the “tortuously somber,” Fast Times, Clueless, and Loser treat sex as a key element of youth education. Central to Heckerling's teen film work are plotlines that feature Stacy, Cher, and Dora as they negotiate their sexual activity (or inactivity).