Say Anything… (1989)
Yeah, yeah, yeah, everyone thinks of this movie as “John Cusack with the boombox,” but there’s a reason it makes every “best romantic comedies” list: It’s a love story on multiple levels and shows just how much people will endure for love. John Cusack stars as Lloyd Dobler, an slacker/aspiring kickboxer in love with Ione Skye’s Diane Court, the class valedictorian. Classic.
Credit Universal