Bad Boys. The original one with Sean Penn. http://en.wikipedia.org/wiki/Bad_Boys_%281983_film%29 Not too proud of this, but I spent some time in one of the places that was filmed in my youth (14). :( St. Charles youth center in Illinois. They filmed the Cafeteria scenes in the old Cafeteria building @ St. Charles. The rest was filmed at IYC Joliet, which is right next door to the big boys house.
Then Cool Hand Luke
The Green Mile
Escape from NY which was technically a prison movie :)
American History X
Without doubt, Midnight Express & Papillon by far. Both movies that leave you totally exhausted by the time they are over.
Escape from Alcatraz ...!