10 Movies That Make Prison Look Like an Awesome Place

Not going to lie: We would not want to be in the jail from Escape Plan. One of these, though…that might be alright.


10. Shawshank Redemption

Prison: Shawshank State Penitentiary
Perks: Shawshank has all sorts of privileges you just won't find at other maximum security facilities. You can get just about any item of contraband you want, security is totally cool with you hanging up posters of whoever the current sex symbol is, and pets are allowed too, so your crow won't get lonely while you're locked up. The best part of being at Shawshank, though, is that you get to have your life narrated by Morgan Freeman. The most inane things, like carving chess pieces or doing taxes, suddenly have a fascinating dramatic weight to them when recited by his soothing voice. In fact, the inmates at Shawshank love it there so much, most would rather hang themselves than return to the outside world.
Potential Drawback: The occasional visit from “The Sisters.”

9. Victory

Prison: German POW Camp during WWII
Perks: When Sylvester Stallone and Michael Caine got captured during WWII, they ended up in the custody of the most easy-going Nazis ever. Rather than starve them, torture them, or perform genetic experiments on them, the Nazis challenged the prisoners to a rousing game of soccer. Stallone and Caine see the game as the perfect opportunity to plot their escape, so during the confusion at the end of the game, they slip away, leaving their cushy soccer prison to rejoin their brothers in arms, who are getting shot at by German tanks. Wait…what the hell were they thinking?
Potential Drawback: If you win, the Gestapo might brutally murder you.

8. American History X

Prison: California Institution for Men in Chino
Perks: Edward Norton stars in American History X as a neo-Nazi who goes to prison for double murder. Now, usually, when people go to prison, they end up learning lessons like “don’t drop the soap,” or, “hey, a toothbrush can make a great shiv!” But rarely do they become nicer, gentler, more understanding people. But that’s exactly what happens to Norton. He gets assigned to do laundry with an African-American (gasp!) and in time grows to care for him. Eventually, the once murderous asshole neo-Nazi learns peace and racial unity and leaves prison as a kind, beautiful person.
Potential Drawback: Other members of the Aryan Brotherhood may not get your new “peace, love and happiness” routine, and you may not get to keep breathing.

7. The Longest Yard

Prison: Allenville Federal Penitentiary
Perks: In this movie, prison is basically just a football fantasy camp. Adam Sandler stars as an ex-NFL quarterback who gets locked up and is asked by the warden to create a prisoners’ football team, so he holds tryouts, trains the prisoners, and gives them uplifting speeches. All of this leads up to a big game against the guards that – spoiler alert! - they actually win, despite it being fixed the other way. In addition to playing football all day, you also get to hang out with Chris Rock and Burt Reynolds.
Potential Drawback:  If you play a bad game, Adam Sandler might make you watch Jack and Jill as a punishment.

6. Shutter Island

Prison: Ashecliffe Hospital for the Criminally Insane
Perks: If you haven’t seen this movie, we’re about to ruin the ending here, but it turns out that Leonardo DiCaprio is a crazed prisoner who thinks he’s still a cop. Ben Kingsley, his doctor, decides that he’ll allow Leo free rein all over the island to play out his cop fantasy, which will somehow convince Leo that he’s not really a cop anymore…yeah, we didn’t really get it either. Anyway, Leo’s free to do anything he wants despite the fact that he’s a violent wife-murderer. So…bonus?
Potential Drawback: Your prison psychologist, Ben Kingsley, is a fucking crackpot who probably won’t help you with your issues.

5. Stir Crazy

Prison: Arizona State Penitentiary
Perks: In Stir Crazy, prison just seems like pure fun. Gene Wilder and Richard Pryor befriend just about everybody, from the bank robber to the serial killer, all while making fools of the guards every step of the way. Any prison that lets you enter a rodeo has to be considered an awesome vacation option for the budget-conscious traveler.
Potential Drawback: You may have to take part in an overly long escape sequence while dressed as a clown.

4. Jailhouse Rock

Prison: This prison name was never revealed, probably because people would be committing crimes all over the place just to try to get into it.
Perks: The first line of the title song to this movie really says it all: “Warden threw a party in the county jail.” Really? Sweet! That warden sounds awesome! Even good prisons like Shawshank had dicks for wardens, but this guy throws open the gates and lets the inmates sing and dance and do whatever they please. Even hook-ups seem much more, um… consensual in this prison: “Number 47 said to Number 3, ‘You’re the cutest jailbird I ever did see, I sure would be delighted if you bunked with me.’” Call us nuts, but that sounds a hell of a lot better than being gang-raped in the prison kitchen.
Potential Drawback: You may end up dancing with a wooden chair, which sounds suspiciously like slang for being beaten to death with furniture in the rec room.

3. Chicago

Prison: Cook County Jail
Perks: Pretty much everything that makes Jailhouse Rock cool applies here, plus Catherine Zeta-Jones in lingerie.
Potential Drawback: Renee Zellweger is there, too.

2. Death Race

Prison: Terminal Island Penitentiary
Perks: In a really awesome-looking dystopian future, prisons are now for-profit organizations, and Jason Statham is locked up in a jail that holds competitive stunt races. The warden offers Statham his freedom if he agrees to drive a tricked-out Mustang through the Death Race, which seems like more incentive than you’d really need. Seriously, screw freedom - we’d drive a machine gun-laden sports car through Midtown traffic any day of the week for nothing.
Potential Drawback: If you’re not the driver, there’s a pretty good chance you’ll end up as road kill.

1. Caged Heat

Prison: Connorville Penitentiary
Perks: This one doesn’t really need a lot of explanation. Caged Heat is a cult film about a bunch of horny, violent women locked up in prison. It popularized the “women in prison” movie genre (which we were very happy to find out is indeed considered a real genre). If only Blockbuster had made that a section, they might still be around today…
Potential Drawback: Rampant STDs.