Directed by Cameron Crowe • 1989 • United States
Starring John Cusack, Ione Skye, John Mahoney

Cameron Crowe made his auspicious directorial debut with this beloved teenage romantic comedy, which breathed new life into the high-school movie with its refreshingly authentic characters and irresistible sense of youthful optimism. John Cusack became a Gen X icon with his eminently appealing turn as Lloyd Dobler, a slacker misfit who sets out to defy the odds by winning over the smartest and most popular girl in school (Ione Skye), while the image of him blasting Peter Gabriel from a boom box below her window has taken its place as one of the defining pop-culture moments of the 1980s.