Lloyd Dobler. Say Anything is one of the best movie romances ever. The "pretty girl falls for the underdog" story has been done many many times, but in this film you actually believe it.
The film begins right after high school graduation. Lloyd (played by John Cusack) is seen as painfully average by pretty much everyone, save his three best friends. He is an aspiring kick boxer and lives with his sister (played by Joan Cusack) and her son. Lloyd is also hopelessly in love with the lovely valedictorian Diane Cort...even if he's only talked to her once. Diane agrees to go to a party with Lloyd and through out the course of the evening (and the summer) they both learn more than either anticipated.
I am a big fan of Cameron Crowe and this film is his directorial debut. He has since made many other films that you will no doubt hear me talking about at another time, but this is still one of my favorites. Crowe's use of music in his films is flawless. Lloyd holding up his boombox outside Diane's window and playing Peter Gabrial's "In Your Eyes" is one of the most iconic scenes of the 80's. Keep an eye out for cameos from Jeremy Piven and Don "The Dragon" Wilson. This film has honesty, feeling and heart without the melodrama so often imbued in high school films. It also happens to be one of the most quotable movies ever. Watch it. I'm not going to guarantee you'll love it, just that you should.