Number 10 - Synecdoche, New York
Watching this movie requires a couple preconditions. First, you probably should have seen some Charlie Kaufman movies already so that you know that nothing is going to be normal. Second, you should understand that when you watch this movie, you're watching it for the first time to get the first viewing out of the way.
Now I'm ready to watch it for real to see what was really going on - what was real and what wasn't. For example, one person's house is on fire. I don't mean there is one scene in which someone's house is on fire. I mean that her house is continually on fire. She buys it in that condition, and in the three or so scenes that take place there later, several years later, it's still on fire.
With a movie like this, I left the theater with a dual feeling of fascination and confusion. Sure there's a chance that another viewing could reveal a stinky turd underneath. But I have a feeling that watching Synecdoche, New York again will be really rewarding. Since I loved Eternal Sunshine of the Spotless Mind, I trust Kaufman.