Jail is not a place I ever want to go. Sure, they probably wouldn’t make me race for my life like they did in Death Race, but there would almost certainly be raping and that’s not for me, thanks. But jail is different in the movies and these 8 guys might make pretty good cellmates.
8. Lt. Gen. Eugene Irwin from The Last Castle
I’m not going to pretend like The Last Castle isn’t a shitty movie, but there’s a lot of satisfaction to be had from watching the epic pussy of a warden, played by James Gandolfini using an inexplicably whiny voice, get what’s coming to him. Sure, Redford was too old to really look like a bad-ass, but that only made the warden’s humiliation that much sweeter.
7. Frank Morris from Escape from Alcatraz
He looks kind of like a mummy these days with his clear skin and his oddly smooth face, but Clint Eastwood has been a serious tough guy since the late ’40s. If anyone was ballsy enough to portray the guys who may have actually escaped from the infamous island prison, it was Clint. I like to think that I could plan a daring escape like Frank did, but chances are I would just curl up into a ball 21 hours a day.
6. John Coffey from The Green Mile
Sure, he could pick you up and shove your leg down your own throat if he was to get mad, but this magical giant of a man would never do that kind of thing. He’s kind of like Lenny from Of Mice and Men only he has wizard powers. Plus, since he’s so religious, he probably wouldn’t go drinking all of your toilet wine.
5. Hannibal Lecter from Silence of the Lambs
It’s impressive for a little old man like Lecter to warrant one of those crazy Magneto-like Plexiglas cages. Plus, the way he escapes from his cell toward the end and decorates it with the flayed carcass of a cop gets him extra style points. He should have his own show on HGTV that helps psychopaths decorate with internal organs. It would only be slightly more horrific than HGTV’s current line-up.
4. Capt. Hilts "The Cooler King" From The Great Escape
There are few guys on the planet that could share the screen with Charles Bronson and still look like the toughest guy in the room. Steve McQueen definitely pulled it off, if not for his ridiculous motorcycle chase scene alone. He was willing to give up his own freedom to save the rest of his buddies and you have to respect that.
3 Paul Crewe from The Longest Yard
I honestly don’t think Adam Sandler’s version of the aging ex-football star was that bad, but Burt Reynolds was everything you could want in a smart-ass prisoner. He told the warden to F-off at every possible opportunity and helped his buddies beat the shit out of a bunch of guards. Also, replace the football with a heavil armored car and you have the same exact plot as Death Race.
2. Luke from Cool Hand Luke
Of all the prisons on this list, Luke’s work camp would be the one I would want to go to. It was like summer camp for criminals. But, that still wasn’t good enough for Luke. He went on raising hell for almost no reason. You have to respect a guy that’s willing to take punishment just for the sake of stirring shit up.
1. Andy Dufresne from The Shawshank Redemption
Where most guys in jail want to bend you over your bunk and relive their prom night, Andy wanted to make jail a little nicer for everyone involved. He played classical music over the PA and brought everybody beers. He was probably handing out HJs at night, too. They had to cut that part out, though. Nothing hurts Oscar potential like too many handjobs.