John Cusack had a pretty long reign (nearly 20 years) as the choice leading rom-com man. He was able to simultaneously project a sweet naivete and slick cynicism, which made him an appealing hero to women and a cool drinking buddy to men. His virginal college student in The Sure Thing is more the lovable naïf, while his obsessive record-store geek in High Fidelity is more the withering cynic, but he strikes a balance in his key film, Cameron Crowe's Say Anything. Cusack's Lloyd Dobler is a unique romantic lead: his (platonic) best pals are all women, and aside from his kickboxing, he has no higher aspirations than to woo and win over Diane Court (Ione Skye). Like any Cusack character, he can talk a good game, but Lloyd is also completely without guile. This intense honesty makes him both attractive and slightly scary. Still, Diane ultimately recognizes that he's a better man than her lying father. Good thing to know that, even if you can't afford jewelry or flowers, you can win a girl over by standing beneath her window and holding up a boombox blaring Peter Gabriel's "In Your Eyes." A generation of filmgoers has grown up thinking of that as the classic romantic gesture.