Most Pacino or De Niro classics, especially The Godfather I&II, Scarface, Goodfellas and Taxi Driver
Oceans films
Batman Trilogy
Anything Tarantino
Fight Club
Donnie Darko
Stranger Than Fiction
The Crow
Cool Hand Luke
Get Carter (Caine, not Stallone)
Rocky 1-4 and 6
Gran Torino and nearly anything directed by Eastwood or his westerns and Dirty Harry series
Anything by The Coen Brothers
300
Shawshank Redemption
Boondock Saints
Most Seth Rogen/Judd Apatow stuff
Anything by Wes Anderson
V for Vendetta
Most Bond films, especially with Connery or Craig
Drive
12 Monkeys
Legends of the Fall
Steve Carrel and Ben Stiller's good movies
Anything with zombies
This could go on for a while...