1. Garden State
Zach Braffs intelligent, unusual film fuses the ManComic traits with the quirky india feel that so many have come to love/loathe (cross out as appropriate). He plays Andrew "Large" Largeman, a struggling and depressed actor who returns to his hometime for his mother's funeral. There, he meets Natalie Portman's Sam, herself a pathological liar with an intensely quirky personality, and they strike up some semblance of a relationship within their equally messed-up personal lives and amongst the inherent dysfunction of their families and friends. Coupling some fairly dark humour with a subtle and sensitive study of mental illness, Braff creates a really satisfying take on the genre, and an excellent film in general. The crises of the film generally occur outwith the central relationship, however, and it's in exploring the difficult relationship between Andrew and his father and friends that it truly excels. Braff's work as a writer, director and actor has been consistently underrated, and it's a real shame that - through no real fault of his own - he hasn't been able to fully expand on this promising start.
So that's it! For more examples, consider: Youth in Revolt, the Graduate, 10 Things I Hate About You, Zombieland, the Amazing Spiderman, 50 First Dates, Music and Lyrics, the Wedding Crashers, Elizabethtown. I'd love to hear suggestions for more - let me know in the comments section below!