Prison movies have been around for decades offering a variety of glimpses into how to break free and stick it to the Man. While we certainly had a cornucopia of options to choose from, we tried to narrow it down our selections to grittier and more real-world depictions as opposed to the extraordinary scenarios seen in films like Face/Off, Fortress, Escape from New York and Time Bandits.
We also went light on options involving the military as those types of films could really offer their own list (though there is a cheat here and there). Still, however deserving, you won’t see flicks like Rescue Dawn and The Last Castle in our final picks.
Last but not least regarding the things we tried shying away from, our preference for actual prison-type scenarios kept us away from the whimsical (apologies to the Leia rescue in Star Wars, Magneto in X2, Joker in The Dark Knight and, of course, the prison break in Guardians of the Galaxy). Still, you may find an option or two that strays from that. (Hypocrisy is the spice of life.)
With our MOs and mea culpas now accounted for, let’s tackle the 19 Best Prison Movie Escapes of All Time. See if you agree.
19. Cube (1997)
Cube tells the story of six strangers placed, against their will, into a cube-like structure rigged with deadly traps reminiscent of the Saw films. But don’t call this one a copycat. It was made seven years before the original in that more successful (financially) horror series. We actually prefer Cube to most of the Saw films, though the same can’t be said for Cube 2 and Cube Zero. The original has risen to cult status, and according to the Hollywood Reporter, we could soon be getting a remake.
Whether that happens or not, Cube gets the nod for having one of the best and bloodiest prison movie escapes ever created. For starters, the genius design of mathematician David W. Pravica is used to grand effect during the film’s climax. Furthermore, the story and direction of Vincenzo Natali does a splendid job of keeping those of us who hate math invested in what is going on through the character of Kazan, and Andrew Miller’s performance as the unlikely autistic savant hero is a big plus.
18. Oldboy (2003)
Oldboy is one of the first films based on a comic to show the true potential in the partnership between sequential art and film. While there had been good, fun comic book movies made before director Park Chan-wook decided to take on the Nobuaki Minegishi and Garon Tsuchiya manga, there had never really been any that made you stop and say, “That deserves an Oscar.”
The tale centers on a man, Dae-su, who wakes up after being kidnapped and imprisoned for 15 years. His captor then contacts him with an ultimatum: discover the reason for his imprisonment inside of five days, or Mi-do, his new lover, will die. Dae-su’s journey is filled with plenty of twists and turns and an earth-shattering revelation, but it also sends a message that merely getting out of a physical prison can’t give one the freedom they desire. In other words, can you really ever “escape”?
17. The Way Back (2010)
The 2010 film The Way Back tells the story of Janusz Wieszczek (Jim Sturgess), a military officer from Poland who is placed into a Soviet Gulag during World War II via a coerced confession from his wife. While in the prison, he colludes to escape with a group of fellow prisoners that include an American engineer, an actor, a hardened Russian criminal, and others from differing walks of life.
They break out under the cover of some track-concealing snow, but their journey is hardly complete. Over the next several months, they will have to brave harsh terrain, the ever-expanding reach of Stalin’s Soviet Union, and each other in order to find true freedom. The film is based on the memoir of Slawomir Rawicz, a former Polish prisoner of war who walked 4,000 miles following his escape during World War II. This particular prison escape is made even more impressive when placed into that context.
16. Room (2015)
Brie Larson won the Academy Award for Best Actress thanks to her work in this drama about a mother who raises her little boy inside of a small shed. Ma does her best to give Jack (breakout star Jacob Tremblay) a normal childhood in spite of the fact that the pair are being held captive by her rapist. As the 5-year-old gets older and starts to ask more questions, she hits her breaking point and decides that it’s time to venture out into the real world, even at the risk of the life she and her son have built together.
Far from your typical prison break film, this one is riveting because of the performances by its two leads, as well as the masterful job that director Lenny Abrahamson does building tension on both sides of the shed door. This film speaks to the claustrophobia and dehumanization that goes along with imprisonment, as well as the inevitable lost feeling one must cope with after breaking free and finding their place in the world. What makes it almost unbearable for viewers is that we are forced to witness our heroes experience those sensations while knowing they’ve done nothing to deserve the trials they’ve been given.
15. Breakout (1975)
Robert Duvall and Charles Bronson star in this classic prison break film that is often overlooked in spite of the fact it was one of the first major studio films to take on a pretty important development in film marketing — “saturation booking.” The strategy consists of releasing a heavy amount or prints at once and preceding it with a major advertising campaign in the opening week. It’s pretty much commonplace in the 21st Century, but in 1975, it was unheard of and resulted in a $7.5 million gross. The film ended up grossing $16 million altogether, which, when adjusted for 2016, is around $77 million.
The story centers on a bush pilot (Bronson), who is hired by an innocent man’s wife to break him out of a Mexican prison. Duvall is Jay Wagner, the man doing a 28-year stint. The film also stars Jill Ireland, Randy Quaid, and Sheree North, and features a pretty cool ending complete with propeller decapitation. Well, decapitation is putting it nicely. It’s more like a complete body decapitation, which you can see here if you don’t mind spoilers.
14. Con Air (1997)
Con Air, Nicolas Cage’s followup to The Rock, was also his second foray into big budget action movie territory. Prior to these two films, the Francis Ford Coppola relative plied his trade in quieter films like It Could Happen to You, Leaving Las Vegas, Wild at Heart, Peggy Sue Got Married and Moonstruck. Thoughtful, funny, well-composed — Con Air shares none of these attributes with Cage’s previous work, but it’s definitely your movie if you like bad dialogue, worse acting, and over-the-top action sequences.
The premise involves a prison plane transport that is hijacked by its captives. Cage is Cameron Poe, one of the only innocent souls on board, who is tasked with taking down the hijackers to save his own life and get reconnected with his family. It’s sort of like Die Hard at 20,000 feet, sans coherency, and features what is perhaps Cage’s most hilariously awful accent ever, which is saying something. Still, we love the guy, and freely admit he can turn out some great performances when he has a mind to.
13. Escape Plan (2013)
Sylvester Stallone and Arnold Schwarzenegger co-star in Escape Plan, which we thought was pretty good, especially Jim Caviezel’s performance — intense, serious, and competent enough to rise above the hokey material. Sure, the film could have done better at the box office with a finish of $137 million in spite of having what once were the two biggest names in Hollywood sharing screen time, but considering it took just $50 million to make, that’s nothing to sneeze at!
Stallone is Ray Breslin, a “structural security expert,” who designs the toughest maximum security prisons in the world — places that are considered “escape proof.” Of course, as fate has it, Breslin gets his chance to put that theory to the test when he’s framed by an unknown enemy and has to go into lockdown inside one of his very own structures. Funny how that works! It’s a typical Sly-Arnie vehicle made a couple of decades too late, but it’s still a lot of fun.
12. The Man in the Iron Mask (1998)
Historical inaccuracies aside — after all, this is a film by Randall Wallace, the screenwriter behind Braveheart — The Man in the Iron Mask offers a pretty thrilling third act, as the newly reformed Three Musketeers are given a brief window of time to rescue Philippe, the kindhearted brother of Louis XIV, who has been locked away in a prison inside of an iron mask for much of his young life. The real Louis (both parts are played by Leonardo DiCaprio) is a human monster intent on keeping his brother a prisoner and lording power. He is protected by D’Artagnan (Gabriel Byrne), one of the original Musketeers.
The “real” Man in the Iron Mask is often named as Eustache Dauger, and if true, he was not of noble blood, nor was he of the noblest of reputations, having been involved in “debauched” affairs and the killing of a man in a drunken brawl, according to the 1988 book The Man in the Iron Mask by John Noone. Of course, we’re talking about the 1600s here, so a certain amount of “artistic license” is understandable. There have been film and TV versions of this story going all the way back to 1909, and we’re sure nobody got it right then either.
11. Public Enemies (2009)
Public Enemies isn’t the best gangster film ever made, nor is it the pinnacle of director Michael Mann and star Johnny Depp’s careers. Still, it is hard not to appreciate the thrilling jail break scene in which Depp (as John Dillinger) cons his way out of a jail cell one room and floor at a time using a piece of wood carved to look like a pistol. Mann uses a handheld approach as we follow Dillinger through the claustrophobic halls and cells of a correctional facility.
Depp sells the intensity beautifully, to the point that if you’re not sure of what you’re watching and just view the scene on silent, you can completely understand why the jailers and warden are pissing themselves. Based on a true story, only historians know how accurately the movie nailed this piece of Dillinger canon. All we know is that it’s a pretty fantastic three minutes of moviemaking.
10. Cool Hand Luke (1967)
Sheesh, the late ’60s and ’70s were depressing — at least in the annals of filmmaking. The pessimism was inescapable, made worse by the fact that the filmmakers and talents were really good at what they did. Many of the era’s films gave us lovable characters, people we truly wanted to emulate, only to have them crushed by the foot of society for being true to what they were. Cool Hand Luke is a textbook example of what we’re talking about.
In it, we meet Luke (Paul Newman), a cool rebel type with a good heart and an undying need for freedom. Luke’s life would go a lot smoother if he would just stop trolling everyone at the correctional facility where he’s sent for a petty crime. Nope. Not in his DNA. Unfortunately, and this is a SPOILER ALERT for those of you who haven’t seen it, Luke is shot and killed during the film’s climactic jailbreak and pursuit. His bravado does give hope to his fellow inmates, though, so that’s something. Before it all goes down, we are given some pretty great scenes between him and enemy-turned-friend Dragline (George Kennedy). Just enough to make it hurt when they pull the rug out from under us.
9. The Count of Monte Cristo (2002)
The 2002 version of The Count of Monte Cristo isn’t exactly a faithful adaptation of the Alexandre Dumas novel, but it sure is a lot of fun. Watching Edmond Dantes (Jim Caviezel again) go through the transformation from simpleton to self-made noble looking to avenge a past betrayal is a vicarious daydream to anyone who’s ever wanted to taste the sweet juices of payback. Throw in a sniveling Guy Pearce in the Mondego role (lead baddie) and the stage is set for an epic swashbuckling tale of revenge.
What makes it all work remarkably well is the jailbreak sequence that punctuates a long and frustrating time spent at the Chateau d’If prison for Dantes, as he makes the switch from buffoon to badass. We like this guy, but know he’s too hapless in the beginning and he will need a little breaking in before he can take up the challenge that fate has in store. Unfortunately, he has to hit rock bottom before anything gets better. Thankfully, Richard Harris’ Abbe Faria is there to guide him — not only in his escape from the prison walls, but also in the ensuing spiritual journey.
8. Snowpiercer (2013)
Snowpiercer is a rarity on this list because of its fantasy world setting, as the remnants of mankind are forced aboard a train that goes round and round the world out of apparent necessity. It’s too cold for anyone to exist outside of the steel-and-wheels, so survivors are cordoned off into a class system that finds our impoverished heroes thrust to the back and treated less-than-human. The “escape scene” lasts for pretty much the entire film, as our protagonists take on hordes of soldiers in their bid for the main engine.
Snowpiercer was a tricky one to bring to film (it was originally an acclaimed graphic novel), but director Joon-ho Bong (Mother) has a fantastic cast that includes Chris Evans, John Hurt, and Ed Harris to help with the journey. The feeling of imprisonment escalates thanks to the fact that Bong keeps nearly all of the action onboard the train and, in so doing, does a capable job of making the viewer feel trapped. This movie hardly did big business at the box office, but it’s incredibly worthy of a watch or two.
7. Runaway Train (1985)
Like Snowpiercer, Runaway Train utilizes its titular transportation and the snowy elements for a thrill ride of epic proportions. This one is set in the contemporary world and doesn’t include some of the more off-the-wall futuristic concepts of our previous entry, but it is, nevertheless, a terrific companion piece and a natural choice to accompany Snowpiercer if you’re ever in the mood for a blustery double feature following the prison escape theme.
Jon Voight is one of two escaped convicts in the film, the other being a stellar pre-direct-to-video Eric Roberts. They’re stuck aboard a train with a female railway employee (Rebecca DeMornay) when the lead engineer dies, leaving the three of them alone to figure things out. Meanwhile, they are pursued by a ruthless security head, and they’re running out of track. Insert amazing finish, and you’ve got one of the best movies of the 1980s.
6. The Escapist (2008)
Frank Perry (Brian Cox) isn’t going anywhere if the prison system has something to do with it. He’s 14 years into a life sentence without the possibility of parole, so there is little to lose when he decides to break free and reconnect with his estranged and sickly daughter. He seeks the assistance of four other men — “escapists,” a ragtag bunch equally fed up with the hell they’re living in day-to-day — and makes a break for it.
Much of the movie is an escape sequence taking place in the sewers, tunnels and underground rivers of London. But what makes the film work so well is how it plays with time, switching back and forth from the high-tension escape to the past events building up to it. While it can be a hokey device in the wrong hands, director Rupert Wyatt (Rise of the Planet of the Apes) knows where to find the balance and does a remarkable job of giving viewers full-blooded characters in the quiet moments between the action.
5. O Brother, Where Art Thou? (2000)
The Coen Brothers update of Homer’s The Odyssey captures the essence of Depression era America like few other films. Part Steinbeck but, like most of the filmmakers’ catalog, strikingly original with pitch-perfect casting and dialogue, O Brother, Where Art Thou? is a rare gem of a film. The plot centers on a hapless trio’s escape from a Mississippi chain gang. Along the way they inadvertently become country music sensations and run into one wacky obstacle after another.
The escape elements dominate much of the film with the Coens expertly weaving in 1930s updates of classic Greek characters through a contemporary lens. It’s all wonderfully nostalgic to the older crowd and indubitably hilarious to those unaccustomed to some of the lightning-quick lines and whimsical speech patterns. The music is also nice toe-tapping fun, even if you’re not that big of a fan of country music. Both a smart and feel-good prison break movie, from beginning to end, O Brother, Where Art Thou is a true rarity.
4. The Great Escape (1963)
The Great Escape brought a number of the finest talents in entertainment together in director John Sturges (The Magnificent Seven) and novelist-screenwriter James Clavell, of Shogun fame. The pair’s collaboration to bring the Paul Brickhill book to life picked up steam with an enigmatic cast consisting of Steve McQueen, James Garner, Richard Attenborough, Charles Bronson, James Coburn, and Donald Pleasance, to name a few.
It’s a film with the kind of talent on both sides of the camera that seems nearly impossible to assemble, and the rewards are obvious. The plot centers on Allied POWs, who hatch an escape plan from a German camp during World War II. What we love about The Great Escape is how it captures the spirit of the Greatest Generation while ironically offering ultimate escapism in a film where the heroes are confined for much of it. Everything about this movie works, and even though it clocks in at a hefty 172 minutes, the pacing and star-power keep you from getting bored while giving the large cast plenty of chances to shine.
3. Escape from Alcatraz (1979)
Clint Eastwood was the perfect choice to play the ringleader of the legendary trio that many believe successfully escaped from the supposedly inescapable Alcatraz Island prison in 1962. The film was made 17 years after the attempt by Frank Morris and the Anglin Brothers that was depicted in the book by J. Campbell Bruce. Behind the camera was Don Siegel, Eastwood’s mentor and the man who taught him much of what it means to be a director on the set of films like Dirty Harry, Coogan’s Bluff, The Beguiled and Two Mules for Sister Sara. It’s their final collaboration, and one of their best.
Much of the buildup isn’t so historically accurate, but the escape is like watching the real thing unfold, papier mache heads and all. Part of that authenticity comes with how Siegel opts for the ambiguous ending, with a slight lean towards escape. Ultimately, you’re left to draw your own conclusions, which only adds to the film’s mystique and makes you want to learn more about the real thing. Our inner rebels kind of make us hope they made it — after all, armed robbery was really their only crimes. Seemed like nice guys.
2. Papillon (1973)
With a Papillon remake on the way — with Charlie Hunnam attached to star — now is the time to revisit this classic film starring Steve McQueen and Dustin Hoffman as two prisoners who befriend one another inside a cruel French prison. The title of the film, fittingly enough, means “butterfly” and refers to memoirist Henri Charriere’s tattoo and nickname. The film is based on his autobiography.
McQueen plays Charriere, and Hoffman is Louis Dega. The prison is an island far removed from society, so escape is unlikely, but that’s not enough to stop these two, nor break their spirits, as they endure years of punishment and cruelty while simultaneously strengthening their bond of friendship. The emotional elements that go into it make for a thrillingly tense finale. Director Franklin J. Schaffner handles the Dalton Trumbo-Lorenzo Semple Jr. script with care, and McQueen keeps his machismo in check long enough to show a softer side. It’s a great film, and it’ll be interesting to see what Hollywood does with it.
1. The Shawshank Redemption (1994)
Stephen King is known for his horror, but this is the best thing he’s ever written, and is definitely one of the very best movies adapted from his work. Tim Robbins and Morgan Freeman are memorable as the films’ two leads, but the supporting cast of fellow inmates don’t get enough credit. The always underrated William Sadler, Gil Bellows, and James Whitmore each do their part to keep the tension unbearable. Villains come on both sides of the bars, and it’s hard to tell which ones are worse.
The film does a great job of rope-a-doping you into assuming the worst, but it only sometimes delivers on those dire expectations. The twist ending is likely known to most of you by now, but we’ll hush up for those who haven’t seen it (seriously, get it together and go watch it now). All we can say is that the payoff is well-earned for both our surviving characters and the viewer. This film never gets old, and, if it’s not considered one already, it’ll will go down as one of the best films ever made.
Well, that’s it. Our sentence is up and we’re gonna bail. Before that happens, though, we want to hear your thoughts. Which prison escape films would you agree warranted inclusion here, and which ones did we miss? Share your thoughts in the comments section!
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