'cool' movies

[Sooga]

Looking through my DVD collection, I realized that I really like 'cool' movies. What is a 'cool' movie? It's a movie where cool/interesting people do cool/interesting things. Examples of 'cool' movies I have seen or are in my collection:

Ocean's 11 (not the original one)
Poolhall Junkies
Rounders (duh)
Equilibrium
Sneakers
Tao Of Steve
Catch Me If You Can
Roger Dodger
Confidence
Italian Job

I'm sure I left a few off, but those are the ones I can see on my DVD rack... what are some other 'cool' movies that you'd recommend?