These are ones I just keep coming back to:
1. Bladerunner - A great examination of the ramifications of artificial intelligence and visually amazing
2. Heat - I love the fact that the lines are blurred between good and bad
3. Fight Club - A brilliant satire that addresses the frustration of the modern american gen x male. Let's just burn it all down and start over!
4. Donnie Darko - Sci Fi time travel story by way of teenage coming of age movie? Very thought provoking and intense
5. Dark City - Visually stunning and a fascinating look at the nature of memories and how they effect us. One of the most underrated movies of all time.
I think we'd get along juuuuuuuuuust fine!
I tend to like movies that warp our perceptions of reality, and turn our expectations back on themselves. Some of my favorites:
Bladerunner - Also the Phillip K Dick book it was based on,
Do Androids Dream of Electric Sheep
Silent Running - From when I was a kid. It was so
sad when those little robots died.
Pi - Whoa. Just... whoa.
A Beautiful Mind - It's like my fantasy.

K-Pax - What is real?
Memento - This is a masterpiece of warped perception. This movie kept me off balance until the very "last" scene. A wonderful exploration of memory, experience, perception, and trust.
Donnie Darko - Messed up, wacked, crazy, insane, and totally cool.
Unbreakable - Another one of my fantasies.

12 Monkeys - Bruce Willis stuck in a strange loop. Need I say more?
Crouching Tiger - Staggeringly beautiful.
Iron Monkey - A wholesome morality play built into a high-energy Kung Fu movie.
Hero - This reminds me of Kurosawa's
Rashomon where the same story is told from several different perspectives.
The Road Warrior - Twisted and cool.
Gattaca - Gives me the willies every time I watch it.
Equilibrium - Gives me the willies too. Contains some powerful scenes.
The Matrix - I wish I could erase my memory and watch this again for the first time.
V for Vendetta - Libertarian Revolution! Yaarrgghh!