30 Best Movies About Breaking Out of Prison, Ranked

These classic prison movies are among the best. These are not the objective best, and they're also not the best prison movies, generally speaking, as there are great prison movies like The Green Mile that aren't as concerned with the idea of escaping. It's clear the sub-genre of prison break movies isn't going anywhere anytime soon, with the following titles being some of the best prison escape movies out there.

30 'Tango & Cash' (1989)

Tango & Cash is a blended comedy and action flick that is remembered for its stellar performances and features one of the most entertaining prison-break sequences in modern cinema. Sylvester Stallone and Kurt Russell star in the 1989 action flick as rival detectives, Ray Tango and Gabe Cash, who are forced to work together to break out of prison after they're framed for murder by a vengeful drug lord, Yves Perret (Jack Palance).

Tango & Cash follows a unique situation that defies the traditional tale of the sub-genre and instead puts the focus on men of the law who unexpectedly find themselves on the other side of the justice system. The chemistry between Stallone and Russell is unmatched and piques the audience's interest with their comedic banter and action. Tango & Cash goes beyond just being a standard prison escape movie and is essentially a thrilling escapade that deserves more recognition than it generally receives. —Andrea Ciriaco

29 'The Next Three Days' (2010)

The Next Three Days stars Russell Crowe as a husband and father, John Brennan, whose world comes crumbling down after his wife, Lara (Elizabeth Banks), is wrongfully convicted of murder. When Lara's final appeal is rejected, she becomes suicidal, forcing her husband to resort to a dangerous course and break her out of prison.

The Next Three Days is widely considered one of the best prison-break movies because it presents the escape not as a flashy action spectacle but as a carefully planned, realistic, and emotionally driven mission. The 2010 thriller combines a believable premise with emotional stakes and relentless tension to essentially show how an ordinary person might attempt an extraordinary—and incredibly risky—escape, rightfully earning The Next Three Days a place on this list. —Andrea Ciriaco

28 'Stir Crazy' (1980)

Stir Crazy is a hilarious prison-break comedy starring comedic legends Gene Wilder and Richard Pryor as friends, Skip Donahue and Harry Monroe, who are wrongfully convicted of robbery and sentenced to over a hundred years in prison. Once on the inside, Donahue and Monroe befriend several of their fellow inmates who eventually agree to help them devise a plan to break out of the joint.

Directed by Sidney Poitier, Stir Crazy marked the second collaboration between Wilder and Pryor, who had previously starred together in the 1976 comedy, Silver Streak, and went on to make a total of four films together. Stir Crazy stands out from other prison-break movies with its ingenious mix of sharp comedy and a creative escape scenario that could only be achieved by a comedic duo like Wilder and Pryor, making the entire concept of a prison break both funny and exciting. —Andrea Ciriaco

27 'O Brother, Where Art Thou?' (2000)

The Coen Brothers' O Brother, Where Art Thou? is a must-see prison-break comedy that features a blend of adventure, comedy, music, and mythology into a story that begins with a chain-gang breakout. Set in Mississippi during the Great Depression, three convicts, Ulysses Everett McGill (George Clooney), Pete (John Turturro), and Delmar (Tim Blake Nelson), manage to escape from prison and set out to find a hidden treasure while being relentlessly pursued across the state by Sheriff Cooley (Daniel von Bargen) and his men.

The Coen Brothers brilliantly turn a simple escape into a fast-paced musical crossed with a myth-inspired road adventure that keeps a firm grip on the audience's attention from start to finish. O Brother, Where Art Thou? may not be a traditional prison break picture, but its uniqueness and bold ambition are what ultimately make it one of the greatest contributions to the genre. —Andrea Ciriaco

26 'Riot in Cell Block 11' (1954)

Riot in Cell Block 11 follows the hardcore inmates of Cell Block 11 who are kept in isolation and are subjected to inhumane living conditions. As tensions between the prisoners and guards reach a boiling point, two inmates, Crazy Mike Carnie (Leo Gordon) and James V. Dunn (Neville Brand), spark a wave of violence and brutality that ultimately turns a riot into an intense hostage situation.

Riot in Cell Block 11 gives audiences a behind-the-scenes look at the American prison system and is known for its array of emotionally complex and intense performances by a highly underrated cast. While some might be put off by the age of the movie, the authenticity and the powerhouse performances make Riot in Cell Block 11 a must-see prison-break classic. —Andrea Ciriaco

25 'The Great Escape' (1963)

The Great Escape, in a word, is great. It's perhaps the quintessential prison escape movie, being a nearly three-hour epic centering on a team of prisoners and their plan to break out of a heavily guarded prisoner of war camp in Germany during WW2.

Steve McQueen might be the most memorable member of the cast, but everyone else is fantastic, too. The characters being so likable makes you root for their escape, and almost the entire film is focused on that titular escape, making for a consistently engaging watch. Plus, there's plenty of suspense and excitement, and it holds up very well after almost 60 years.

24 'The Old Man & the Gun' (2018)

An underrated modern classic from the 2010s, The Old Man & the Gun is admittedly more of a heist movie, but prison escape factors into the plot, too. It centers on an aging thief played by Robert Redford, and takes a generally relaxed and oftentimes comedic look at how he continues his criminal lifestyle even in his old age.

He plans robberies and prison escapes, and though there are some more serious moments, it's quite breezy by the standards of most heist and/or prison escape movies. It's also a very fitting cinematic send-off to Redford, given that it still stands as his last starring performance as of 2023.

23 'The McKenzie Break' (1970)

There are plenty of prison escape movies set during World War II that have German forces as the captors and Allied forces as the escapees, but The McKenzie Break shakes things up. Here, the characters trying to escape are all members of the German army, with the prisoner-of-war camp being in Scotland.

It's also overseen by British forces, meaning this serves to be something of a role-reversal when it comes to English-language prison movie set during World War II. Perhaps its approach was a little unorthodox for it to be a big hit, but it's still a compelling prison movie, and certainly worth seeking out for fans of the genre.

22 'Escape to Victory' (1981)

The first thing that jumps out about Escape to Victory is how eclectic its cast is, given it includes the likes of Sylvester Stallone, Michael Caine, Max von Sydow, and professional footballer Pelé. It's also more than just a prison escape movie; it's also a compelling sports drama.

This is because the premise involves British prisoners at a prisoner of war camp in World War II taking on German opponents, all the while one prisoner plans a daring escape behind everyone's backs. It's certainly a unique type of prison movie, and for its novelty factor and impressive cast, it ends up worth a watch.

21 'Escape From Alcatraz' (1979)

Maybe one of the most memorable Clint Eastwood films in which the iconic actor/director doesn't play a cowboy or cop, Escape From Alcatraz was based on a real-life escape attempt from Alcatraz, the famous island prison located in San Francisco Bay.

One of the things that makes Escape From Alcatraz stand out is the fact that it was filmed in the real-life Alcatraz Prison, as it had shut down in 1963. This gives the film an authenticity that makes the events feel more compelling, even if the film itself doesn't aim to be a 100% accurate retelling of the real event.