There's Gonna Be A Jailbreak...Eventually
September 13, 2021 8:48 AM   Subscribe

I’m working on a piece of fiction, so I’m in search of inspiration: stories (real or not) featuring escapes from prison (or the like). A few snowflakey details.

I’ve got a piece of fiction rattling around in my head where a character escapes from a prison. I’m not especially good at plot logistics, and I know I can handwave it, but I’m hoping that consuming some stories—movies, TV, books (either fiction or nonfiction), reportage, anything—that feature an escape from prison/jail/confinement as a major element will get my gears turning. I’m thinking very much of something like The Shawshank Redemption (and the story that birthed it) as a great example, especially the careful planning that went into getting out.

So while anything with a person (or several) getting out of imprisonment of any sort would be great, I’d be particularly interested in stories where the audience has a clear idea of all the steps that went into it.

Thanks in advance!
posted by xenization to Media & Arts (24 answers total) 2 users marked this as a favorite
Is The Count of Monte Cristo too obvious?
posted by thivaia at 8:51 AM on September 13, 2021 [1 favorite]

Escape from Alcatraz is a film based on a nonfiction book about a 1962 escape. I visited Alcatraz a few years ago, and one of the cells was set up with dummies made to look like the ones the escapees used - I think that may have been done for a TV special.
posted by FencingGal at 9:00 AM on September 13, 2021 [1 favorite]

It's not a film primarily about prison break, but escape from a POW camp (two, actually) is still a major plot element in Grand Illusion, which you should watch anyway.
posted by praemunire at 9:01 AM on September 13, 2021 [3 favorites]

This true case from a few years ago ended badly for the escaped prisoners after a few weeks of freedom. But the getaway itself is quite a story: a prison employee fell in love with a prisoner and helped plan the escape.
posted by nantucket at 9:08 AM on September 13, 2021

There have been quite a few helicopter prison breaks since the first one in the 70s and movies that feature them
posted by TWinbrook8 at 9:21 AM on September 13, 2021 [1 favorite]

It's not often that I have a chance to recommend The Rock. "How in the name of Zeus's butthole did you get out of your cell?"

And, of course, The Great Escape, which depicts the meticulous planning, the breakout and the aftermath of a POW escape.

Bonus points: Chicken Run, which is the Great Escape but folks is chickens.
posted by SPrintF at 9:28 AM on September 13, 2021 [1 favorite]

Escape from Dannemora was a series on Showtime, based on a true story. There's also a book.
posted by lyssabee at 9:35 AM on September 13, 2021

Best answer: Robert Bresson's A Man Escaped is maybe the greatest prison escape film.

From the IMDB trivia page:

Robert Bresson insisted on complete authenticity. Original author André Devigny served as adviser on the film, which was actually shot in the same Montluc prison where he was incarcerated. André Devigny also loaned Robert Bresson the ropes and hooks he had used in his escape.
posted by remembrancer at 9:38 AM on September 13, 2021 [2 favorites]

Professor Van Dusen, the Thinking Machine: The Problem of Cell 13 by Jacques Futrelle (who went down with the Titanic). Also, Papillon by Henri Charrière.
posted by Rash at 9:39 AM on September 13, 2021 [2 favorites]

Éamon de Valera's escape from Lincoln Prison in 1919 is worth a read, even if it's probably a bit outdated now.
posted by scorbet at 9:43 AM on September 13, 2021 [1 favorite]

Not a lot of planning, but a fairly intense visual from Raising Arizona. You can almost smell the sewage. It's very similar to the breakout scene in The Shawshank Redemption, complete with stench, but more planning.
posted by SamanthaK at 9:53 AM on September 13, 2021

Breakout by Richard Stark (aka Donald E. Westlake) has professional thief Parker finally behind bars....but not for long.
posted by leaper at 9:58 AM on September 13, 2021

Best answer: I definitely recommend the memoir "The Great Escape", from which the film was eventually adapted. Even more details about the meticulous planning.
posted by theatro at 10:09 AM on September 13, 2021 [1 favorite]

Best answer: The appropriately named Prison Break television show from 2005 is exactly this. The prison break is planned in exhaustive detail and unfolds step by step across the entire 22 episode arc of season 1.

The show is currently available on Hulu. It got its butt kicked by the writer's strike and some unfortunate plot choices later in its run, but season 1 is some genuinely fine television with some genuinely fine men, and it's a great watch even if you're not looking for prison break plots. I really loved this show.
posted by phunniemee at 10:11 AM on September 13, 2021 [2 favorites]

Futility closet (podcast) covered the
Libby Prison was one of the most infamous prison camps of the Civil War — thousands of Union prisoners were packed together in a converted warehouse, facing months or years of starvation and abuse. The Confederates thought the prison was escape-proof, and in this week’s episode of the Futility Closet podcast we’ll show how a determined group of prisoners set out to prove them wrong.
posted by Mitheral at 10:35 AM on September 13, 2021

The story of Tim Leary's prison escape from I Have America Surrounded and move from there to Liberia, might be of interest.
posted by chiefthe at 10:36 AM on September 13, 2021

Stalag 17. So much planning!
posted by late afternoon dreaming hotel at 10:37 AM on September 13, 2021 [2 favorites]

great escape book +1
posted by j_curiouser at 10:59 AM on September 13, 2021

The Great Escape book +2 (by Paul Brickhill.) Also, One Flew Over the Cuckoo's Nest by Ken Kesey.
posted by Rash at 11:26 AM on September 13, 2021

WWII: The Wooden Horse by Eric Williams [Exec Summ]
WWII: The Colditz Story by Pat Reid [Exec Summ]
WWI: The Road to En-Dor by Elias Jones [Review]
Earlier: King Charles I fails to escape from Carisbrooke Castle
Earlier still : St Paul leaves Damascus in a basket Acts 9:23-25
posted by BobTheScientist at 12:17 PM on September 13, 2021 [1 favorite]

Best answer: The recent movie "Escape from Pretoria," starring Daniel Radcliffe, is based on the memoire of Tim Jenkin, a white South African activist against apartheid whose exploits included deploying pamphlet bombs (which exploded with illegal printed material). Thrown into an older prison in Pretoria in the late 1970s, he escaped by duplicating the keys he saw hanging the guard's belts, measuring by eye alone.

Trailer here.
posted by Sunburnt at 12:46 PM on September 13, 2021

Seconding Escape from Pretoria, it's a great prison break movie.
posted by EndsOfInvention at 4:02 PM on September 13, 2021

Sharkatraz is hilarious and includes some details about escape attempts from Alcatraz.
posted by kinddieserzeit at 11:21 PM on September 13, 2021

Best answer: Another vote for The Colditz Story.
It tells, with great operational detail, the many many escape attempts (some successful, some not) from the high-security POW camp at Colditz Castle in Germany during the war.
posted by vincebowdren at 3:52 AM on September 14, 2021

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