These prison movies are captivating. Get it? Anyway, we hope you enjoy this list.
Caged (1950)
An early entry in the subgenre of women behind bars, John Cromwell’s Caged is about a married 19-year-old (Eleanor Parker) who is locked up after a botched bank robbery in which her husband is killed.
Hope Emerson plays sadistic prison maven, Evelyn Harper, in a story that reveals that prison may be the most corrupting influence of all.
The film was nominated for three Oscars.
The Bridge on the River Kwai (1957)
Is it a prison movie? Or a war movie? We would say it’s both — David Lean’s The Bridge on the River Kwai is a movie that never does what you expect.
Set in a Japanese prison camp in Thailand, the film portrays a battle of wills between captured British P.O.W. Colonel Nicholson (Alec Guiness) and his captor, Colonel Saito (Sessue Hayakawa). Saito demands that Nicholson and his troops build a railroad bridge over the River Kwai, which leads to questions of ethics and honor, and how to maintain your humanity while in captivity.
It was the most successful movie at the box office in 1957, and deservedly won seven Oscars, including for Best Picture. It’s one of those 1950s movies that is both a classic and a joy to watch.
Escape From Alcatraz (1979)
One of the greatest prison movies, this Clint Eastwood film was the star’s fifth and final collaboration with Dirty Harry director Don Siegel. In fascinating detail, it imagines the circumstances of a real-life escape from the supposedly escape-proof Alcatraz Island in 1962.
Eastwood plays the real-life prisoner Frank Morris, whose whereabouts have been unknown since that chilly night in the early ’60s. He’ll turn 98 this year, if he’s still around.
The FBI’s investigation into the escape remains open.
The Shawshank Redemption (1994)
You knew this was coming, so we’re putting it in this gallery nice and early.
One of the most beloved films of recent decades, and pulled from the same Stephen King story collection, Different Seasons, that also spawned Stand by Me and Apt Pupil, The Shawshank Redemption is a story of refusing to surrender your soul.
Tim Robbins stars as Andy Dufresne, a banker sentenced to consecutive life sentences in the killings of his wife and her lover. He befriends Ellis “Red” Redding (Morgan Freeman) — and hatches a plot to dig his way out, while hiding the hole in his cell wall behind a poster of Rita Hayworth.
Cool Hand Luke (1967)
Paul Newman is transfixing as the title character, a man of few words (and hardboiled egg gourmand) who refuses to bend to the cruelty of his Florida prison camp.
Strother Martin, as the captain of the camp, earned a place on the American Film Institute’s 100 Years… 100 Movie Quotes for this monologue that begins, “What we’ve got here is failure to communicate.”
Guns N Roses fans will also recognize it from the opening of the band’s “Civil War.”
Penitentiary III (1987)
The third film in a series of hit independent prison movies written and directed by Jamaa Fanaka, Penitentiary III is extremely worth watching for the Midnight Thud fight alone.
Oh, you don’t know about the Midnight Thud? Thud is the toughest fighter in the prison, a powerful little person (played by Raymond Kessler, aka the WWE’s Haiti Kid) who delivers one of the most captivating fight scenes ever committed to film when he faces off with our protagonist, Too Sweet (Leon Isaac Kennedy).
Also, this is the first of two films on this list to feature the great Danny Trejo. He plays See Veer.
Con Air (1997)
Trejo is one of the murderer’s row of stars who turns up in Con Air, a prison-on-a-plane movie in which Cameron Poe (played by Nicolas Cage, looking incredibly cool) takes on a whole plane full of felons when its Cyrus “The Virus” Grissom masterminds a hijacking.
This is one of those movies that — if you haven’t watched it in a while — will have constantly saying, “He’s in this, too?”
The cast includes John Cusack, Steve Buscemi, Ving Rhames, Dave Chappelle, and many, many more.
The Great Escape (1963)
Steve McQueen leads an all-star cast playing POWs who heroically escape from a Nazi prison camp in this classic, heavily fictionalized story of British POWs’ escape from Stalag Luft III during World War II.
Among the concessions to commercialism: sprinkling three Americans into the action. Thanks goodness McQueen’s Captain Virgil Hilts was there, or else who could have pulled off that spectacular motorcycle sequence (above)?
Hunger (2008)
And now, a prison movie from the other Steve McQueen — the masterful British director whose film 12 Years a Slave won the Best Picture Oscar in 2014.
His directorial debut, however, was Hunger, in which his frequent collaborator, Michael Fassbender, plays Bobby Sands, a real-life member of the Provisional Irish Republican Army who led an IRA hunger strike and took part in a no-wash protest behind bars.
Hunger is a brutal, hypnotic film that skillfully captures the day-to-day dehumanization of the prisoners.
Clemency (2019)
Another grim prison saga that was also the directorial debut of a great filmmaker, Clemency stars Alfre Woodard as a prison ward trying to unemotionally do her job — which includes overseeing the death of a young inmate, Anthony Woods (Aldis Hodge) who maintains his innocence.
Many death-penalty films lecture their audiences (who may have already opposed the death penalty), but Clemency writer-director Chinonye Chukwu does not: She just lays out the facts of the situation, with as much restraint as Woodard’s warden — until emotions eventually make their inevitable break.
This is a wise, patient film that sidesteps preaching and Hollywood hokum in favor of a very chilling, very human story.
The Longest Yard (1974)
On the lighter side, The Longest Yard is a sports movie crossed with a prison movie… and a comedy. The film stars Burt Reynolds as a hard-driving, hard-hitting now-incarcerated former NFL quarterback who is tasked by a nasty warden with assembling a team of prisoners to play against the guards.
How do you think that works out?
Caged Heat (1974)
A very different look at prison life, released in the same year as The Longest Yard. We aren’t going to claim this low-budget Roger Corman production, also known as Renegade Girls, is a great film. But it is the debut of a very great filmmaker: writer-director Jonathan Demme would go on to make Silence of the Lambs, one of the best films of all time, and to repay Corman for his confidence by casting him in the role of FBI Director Hayden Burke.
Silence of the Lambs was also shot but Demme’s go-to cinematographer, Tak Fujimoto, who also shot Caged Heat.
Caged Heat is a cheap exploitation flick, sure, but it contains some Demme hallmarks: strong female protagonists, a strong sense of empathy for the characters, and social consciousness.
A 1975 New York Times story on the rise of “trashy” midnight movies concluded that it “does not set new standards of cheapness, violence or grossness, as most midnight movies seem determined to do. It is a film about women in prison that offers little more than some zippy music, a lot of bosom shots and a perverted prison doctor.”
High praise from the paper of record.
Stir Crazy (1980)
The second film to pair Gene Wilder and Richard Pryor, Stir Crazy finds the duo dressing up as woodpeckers, getting framed for a bank robbery… and being sentenced to 125 years in the pokey.
We’re surprised this movie isn’t mentioned more. Directed by Sidney Poitier, it was the third-highest grossing film of the year of its release, 1980, behind only The Empire Strikes Back and 9 to 5. (It handily outgrossed films including The Shining, Friday the 13th, and The Blues Brothers.)
Liked This List of Captivating Prison Movies?
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Main image: Caged Heat. New World Pictures.