My favourite is The Big Chill. It's been a favourite since my Uni days (when I was younger than the characters), grew even more relevant as I reached the age of the characters. Now, I am as much older than the characters as they were older than me when I first discovered it. I need to re-watch it, and see what else I can take away from it this time.

Second is Casablanca. It is also the last movie I saw in the theatre. (It was a couple of months ago at the 75th anniversary screening, but I love throwing it out there to see the reactions I get)

Third is a wonderful Australian film that is almost impossible to find in the States, called The Year My Voice Broke.

One Flew Over The Cuckoo's Nest.