My Dinner with Andre - Every time I watch it, there's a different interpretation for the movie. Very absorving and thought provoking all in all.
Suna no Onna - Another really twisted and profound movie loosely based on the myth of Sisyphus, and driven by the uniqueness of its plot.
Pi - Love how bizarrely brilliant Maximillian Cohen is. Really engaging stuff.
Fight Club - Pretentious and tacky, but has a rebellious undertone that most men can resonate with. Surprised that it doesn't have a lot of mentions already.
Pan's Labyrinth - Fairy tail for grown-ups. What's not to like ?
Into the Wild - Footloose appeal, smashing soundtrack, keep returning to it.
Movies that I will definitely not watch again, ever - Life is Beautiful, Hotaru no Haka, Dancer in the Dark.