This is a difficult choice. So, I'm going to cop-out with a beautiful list.
Shawshank Redemption
Labyrinth
Moulin Rouge
Big Fish
Running With Scissors
(guess this isn't a list of five) Oh, brother where art thou
Warriors
Return of the Living Dead
The Jerk
Clueless (Yeah, that's right, this is most likely the best movie on this list. I may have just been too embarrassed to say it first.)