Marie de Salle from "High Fidelity"
Lisa Bonet plays an elusive singer named Marie that John Cusack's character has a brief relationship with. The whole movie is dedicated to Cusack going back through his list of breakups in order to prove how he was wronged, when really it's revealed that he just kind of sucks at relationships.
Romeo from "Romeo + Juliet"
Another early Leonardo DiCaprio film was a chaotic retelling of the Shakespeare play "Romeo + Juliet." He stars across from Claire Danes and features gun-wielding rebels and lavish parties. The skeleton of the plot follows the original play, and the star-crossed lovers still die in the end.