For convenience's sake, I'm going to limit this to movies I own:
Honorable mention:
Field of Dreams. Would be ranked, but technically I don't own it, I bought it for someone else. Nevertheless, it's one of my favorites, and I'd be lying if I said I don't get a little catch in my throat when Moonlight Graham steps across the foul line, or when Ray asks his dad if he wants to have a catch.
High Fidelity. I really like this movie, but I can't quite identify with John Cusack's character, as I don't have numerous ex-girlfriends and I'm nowhere near the music snob.
#5: Raiders of the Lost Ark
I can't name anything about this movie that stands out above other parts of it...I just like to watch it.
#4: OfficeSpace
Watching OfficeSpace and having a few beers helps me feel better about school, work, and life in general.
#3: Anchorman
It's stupid, but it's funny. It never fails to make me laugh.
#2: The Royal Tenenbaums
People either seem to get this movie or don't...much like Wes Anderson's work in general. I think it's a wonderfully gentle comedy--yes, even with accidental amputations, suicide attempts, and incestual overtones--that portrays a family that manages in the end to "make it work" and appreciate and love each other despite their many dysfunctions.
#1: Tombstone
This movie couldn't have been more perfectly cast. What great performances by Val Kilmer, kurt Russell, Sam "Beef...it's what's for dinner" Elliot, Powers Boothe, Dana Delaney, Billy Zane...etc. And what a great script.