A few come to mind:
Heat
Star Trek II
Office Space
The Big Lebowski
Casino
Goodfellas
Caddyshack
I could watch any of those on infinite loop over and over, they're all perfection from the first frame to the last. Those popped into my head first, plenty of others but it's bed time.
Disagree with about half your list bdjuf (you asked). I feel you're trying to look artsy/sophisticated to to either the board, or yourself. LOL The Life of David Gale, what a garbage movie that was. Good pick on Vanilla Sky though, that was a very underappreciated movie for sure.