The princess bride. I watched it the for the first time with my dad when I went to work with him on a midnight shift (I was little and it was fun!). We still quote lines to each other. It's a good, old school movie!
Tears of the Sun. This movie (especially the extra commentary from actual victims of ethnic cleansing) made me bawl. It really opened my eyes up and reminded me that the world is WAY bigger than my own little "problems".
Pirates of the Carribean (the first one). Because I secretly love pirates. :)