Prison is a scary place. Even in the movies, it's the kind of place that is impossible to romanticize, and Hollywood can do that with a lot of other terrible places. Prisons are also a place where storytellers can find interesting characters and angles to bring humanity to life. There is nothing good in prison, but there is that, there is humanity. Still, as the movies on this list will prove, you never want to end up there.
The Green Mile
If there is an even worse place to be than regular prison, it's death row. It's even worse if you were to find yourself on death row in Louisiana in the 1930s. That's where our story takes place in The Green Mile and while Tom Hanks' character is somewhat kind, the rest of the guards are a nightmare and the experience looks miserable. Death might be a relief.
The Last Castle
Military prison is no joke, especially when the warden is one like the one James Gandolfini plays in The Last Castle. The movie plays out like a lot of prison movies, in the vein of Cool Hand Luke. One prisoner, unhappy with the unfair treatment of the warden and the guards takes them all on in a battle of wills.
Escape From Alcatraz
Escape From Alcatraz is an all-time classic and a fun adventure movie. It's not fun to see what life was really like on "The Rock." Watching this movie it's easy to understand why people were desperate to escape the "escape-proof" prison.
Cool Hand Luke
A failure to communicate is not why Luke (Paul Newman) was the way he was in Cool Hand Luke. A mere existence on a chain gang in a prison work camp seems like it would be just the worst thing to ever go through. At least you get all the eggs you can eat though.
The Longest Yard
On its surface, The Longest Yard makes light of life in prison. They get to play football and make jokes all day. Dig a little deeper and think a little more and you realize that the only relief from the stress and the boredom of prison is the take desperate measures on the football field. No thanks.
Dead Man Walking
Dead Man Walking, starring Sean Penn as a condemned man on death row is a really hard movie to watch. There is nothing scarier than being in a situation where you know you're going to die and little can be done to save yourself. Instead, you can only hope to take solace in your death by meeting with a spiritual advisor and hope the afterlife is better than where you are.
The Great Escape
Okay, okay, this really is a fun adventure movie, for the most part. Still, there are some dark moments in The Great Escape like Archie Ives (Angus Lennie) cracking and in a move of desperation trying to scale the fence only to be cut down by the guards. As fun, as this movie is, it's still prison.
In The Name Of The Father
The only thing worse than getting locked up for committing a crime is getting locked up as an innocent man. In the classic In The Name Of The Father, that's exactly what happens to a man and his father, played by Daniel Day-Lewis and Pete Postlethwaite, respectively. They spend years in prison fighting for their freedom, which eventually comes, but too late for the father.
The Bridge On The River Kwai
World War II prison camps in the Pacific Theater were no joke. In one of the best movies of all-time, The Bridge On The River Kwai, the brutality of life in the camp is on display for the full run-time of the movie. It's impossible to understand how those soldiers kept their dignity like they did.
The Shawshank Redeption
In one of, if not the best movie of the '90s, two men face life sentences in a brutal prison in Maine in The Shawshank Redemption. The fact that Andy (Tim Robbins) is an innocent man wrongly sent to jail makes it even more brutal. Still, this is the kind of movie where humanity shines through, it's just not how anyone would every choose to experience it.
Bronson
Bronson is a wild movie, about a wild guy dubbed "Great Britain's most dangerous prisoner." Tom Hardy plays the titular character, who is based on a real criminal, and one look at how he acts with those around him and you'll know you never want to deal with anyone like him. The best way to avoid that is to stay out of jail!
Brokedown Palace
Smuggling illicit items into a foreign country is about the worst idea, ever. Starring Claire Danes as Alice Marano and Kate Beckinsale as Darlene Davis, Brokedown Palace tells the story of two young women who make one major mistake and pay the price in the worst way in a brutal women's prison in Thailand.
Escape From New York
Not every prison has walls guards, or even cells. Some, it turns out are just the burnt-out remains of one of the great cities of the world, New York City. In Escape from New York, Snake (Kurt Russell) must navigate an apocalyptic landscape in a chaotic, free-for-all prison on what was once the island of Manhattan. No thanks.
Midnight Express
"Have you ever been in a Turkish prison" is the question Captain Over asks a kid in the spoof movie Airplane! Lost on a modern audience is that the joke is in reference to a movie from 1978 called Midnight Express. It was a phenomenon at the time and really set the bar for just how scary and awful prison can be,
25th Hour
Even though 25th Hour doesn't actually take place in a prison, it's almost worse. Edward Norton plays a convicted man headed to prison, navigating how to prepare. Sometimes the anticipation can be the worst part and there is no better example than this fantastic movie directed by Spike Lee.
Con Air
Once again, we're talking about a movie that while it's a ton of fun on the surface, it doesn't take much to look under the hood and see how terrifying the people in prison are. Just two of the passengers on Con Air, Cyrus the Virus (John Malkovich) and Garland Green (Steve Buscemi) are enough to convince anyone that prison is a bad place to be.
No Escape
Set in the year 2022, the 1994 movie No Escape is completely over-the-top. Similar to Escape from New York, it's about a penal colony on a island, but this time it's no city, just jungle. And there is no escape, if you believe the title. It seems like about the worst place to do time.
The Hurricane
Yet another tragic tale of an innocent man rotting away in prison for decades trying to get someone, anyone, in the justice system to believe him. Ruben Carter was railroaded into a murder conviction in the 1970s and spent years trying to get out. Hurricane tells his story brilliantly, and the good news is that eventually he did get out and declared innocent.
The Dark Knight Rises
There is an old saying about throwing the worst criminals down the deepest, darkest hole in the earth. In The Dark Knight Rises that's exactly where some of the worst of the worst end up, including both Bane and Batman at different times. Only a few have ever escaped, like Talia al Ghul (Joey King) and Bruce Wayne (Christian Bale)
12 Monkeys
Sometimes it's hard to tell the difference between prison and a mental facility. Especially in a dystopian future like the one in 12 Monkeys. In fact, the movie makes the latter look way worse than a simple prison. Either way, you hope to not end up in either one.
Sleepers
Sadistic guards in movies have long been one of the reasons it's clear you don't end up in jail, even - or maybe especially - as a juvenile. Kevin Bacon's character in Sleepers is so evil, so sadistic, that even when the worst happens to him later, you can't help but cheer. And say a little prayer that you never had to go through what the kids in that movie went through.
Deadpool 2
Even in a fun superhero movie like Deadpool 2, you don't want to end up in prison like Wade (Ryan Reynolds) does. Not only do they block his power and allow the cancer to return, he can't be protected from Cable (Josh Brolin)
The Power of One
One of Morgan Freeman's most underrated movies has to be The Power of One. Ultimately it's an inspiring story, but it's not without the cautionary tale of avoiding prison, something his character sadly cannot do in apartheid South Africa.
American History X
If there is one thing to learn about avoiding prison in American History X, it's that you never want to end up like Edward Norton's character. Ever. He is the personification of evil and prison only makes him better at being evil. Not only do want to avoid people like him, you would never want to be in a position to have to be more like him.
Goodfellas
This one is a little tricky. For one, prison for wise guys doesn't look that bad in Goodfellas. There is steak, lobster, and thinly sliced garlic. On the other hand, life in the witness relocation program, eating egg noodles with ketchup, sounds like a miserable existence, so its best to just avoid the whole situation and stay on the straight and narrow.
Papillion (2017)
2017's Papillon is a remake of a movie from 1973 starring Steve McQueen about a condemned man sent to the notorious Devil's Island prison from France. Both movies are great, so it's hard to pick one over the other. Both will scare the pants off you and ensure you'll do anything to avoid something like that.
Stir Crazy
Gene Wilder and Richard Pryor can make anything fun and that includes prison. So while Stir Crazy is of the few movies on this list that audiences laugh through, it still doesn't sell anyone on the idea that prison is the place to be. Quite the opposite, in fact.
The Stanford Prison Experiment
The Stanford Prison Experiment isn't the best movie on the list, nor is it about an actual prison, but anyone who knows anything about the real experience this film is fictionalizing knows just how awful things got. The experiment was to show what happens when regular people are put under the stress of being prisoners and guards in a prison-like situation. The results may make you lose all faith in humanity.
Starred Up
Violence is everywhere in prison and Starred Up makes sure that audiences feel all of it viscerally. It's not an easy movie to watch, and it makes you wonder how anyone could survive inside with the level of violence possible. It's an underrated movie, but not one you aspire to be like.
Jailhouse Rock
One of the many low-budget, quick productions that starred Elvis early in his career was the prison movie Jailhouse Rock. While it doesn't seem like the worst prison on earth and there is singing and dancing, it's still a prison. Maybe the real prison would be having to watch this movie over and over in lockdown 23 hours a day.
Alien 3
Even in the future, prison looks miserable. Maybe even more miserable when you are stuck on a prison planet with nothing but violent criminals and forced to shave your head to avoid lice. And then an alien gets involved. Nope! No, thank you!
Law Abiding Citizen
Everyone want to root for the antihero and in Law Abiding Citizen, Gerard Butler's character is one that is easy to root for. The time he spends in jail, however, is not something anyone could root for. Just like all the movies on this list. It all just sounds awful.
