"The Great Escape"
"The Great Escape"

"The Great Escape" (1963)
What's It About? The film, directed by American journeyman director John Sturges, is based on the book of the same name by Australian author (and former POW) Paul Brickhill, and both recount a mass escape from Stalag Luft III in what was then a part of Nazi Germany (it's now a sliver of Poland), by a motley band of Allied prisoners of war (including Steve McQueen and Richard "spared no expense" Attenborough).
What's The Escape Plan? An elaborate plan involving tunnels, forged documents, impeccable German accents and (of course) costumes, and the original intent was that all 250 prisoners would attempt the escape. The premise of "The Great Escape" is that since all of the great escape artists are under one roof in the prison camp, they can pool their resources and come up with an incredibly intricate scheme that has to see at least some of them make it to freedom. Initially, the Steve McQueen character and the Angus Linnie character attempt an escape via tunneling but are recaptured. After that the work begins in earnest on the real tunnel, with one of the great prison escape tropes utilized when the prisoners digging shake the excess dirt out of their trousers all around the prison, right under those dirty Nazis noses. Finally the tunnel is completed, though it stops 20 feet short of the coverage the nearby trees will provide.
How Successful Is It? Considering the title, not very. Initially, only 76 of the proposed 250 even make it through the tunnel, and most of them are captured or killed during the process. And the divide-and-conquer approach pursued by those who do get out mostly leads to a variety of misadventures: an attempt to steal a German plane is thwarted when the plane crashes; Attenborough's character is recognized in a Nazi-infested train station. Many of the captured escapees are gunned down methodically. Others are captured and returned to their cell, including the McQueen character, although the movie ends on a moment of him methodically bouncing his baseball against the wall, somewhat defiantly, which suggests a certain kind of optimistic future (one of our favorite of the many references to this frequently nodded-to film was the homage to this moment in the opening segment of "Mission: Impossible - Ghost Protocol")
Would It Work In Real Life? Well, it was attempted in real life, although certain aspects were obviously distorted and blown up for cinematic purposes, with most authorities on the subject considering the film version more fiction than factual. As the movie tell us, 50 of the prisoners were shot after the attempted escape, (both the book and film are dedicated to these men) so purely on a numbers basis we'd have to suggest that its result weren't exactly stellar. However no matter how much the movie changed the details and how much the characters were changed or condensed, it's still a hell of an inspirational story that speaks to the bravery of anyone who attempts what they know to be a perilous escape, purely on the principle that escaping is their duty.


Breakout” (1975)
What's It About? When businessman Wagner (Robert Duvall) is framed for murder due to the corporate machinations of his grandfather (John Huston) and sent to a Mexican prison, his devoted wife (Jill Ireland) recruits a devil-may-care pilot Colton (Charles Bronson, in a surprisingly unwooden performance) to effect a daring rescue. Unfortunately she still trusts the grandfather and his lawyer/henchmen, so the escape plans keep getting scuppered until Colton hatches a scheme in secret to airlift the now ailing Wagner to freedom. It's all exactly as daft as it sounds, but it's so totally 70s in cast and execution that it’s almost endearing, if one can overlook the appalling sexual politics (one female actually utters the immortal line “Rape? I should be so lucky!”)
What's the Escape Plan: With the bad guys’ long reach making itself felt even in the form of Wagner’s informant prisonmate, Colton’s early hare-brained schemes, including one in which sidekick Randy Quaid is dressed to be a surprisingly pretty, if extremely tall, “Mexican whore,” go awry, he realises there’s a leak in the camp. But already beguiled by Wagner’s fetching wife (Bronson’s real-life wife Jill Ireland), Colton formulates a final plan involving a helicopter (which he can’t fly) setting down in the prison exercise yard and a diversion at the front gate to lure away the guards.
How Successful Is It? Bizarrely, this is the plan that works like a dream, despite the pilot losing his nerve at the last moment and Colton having to fly the helicopter, wobblily, himself. But with the grandfather’s agents all around, the copter is forced to land for a customs inspection where the final showdown takes place, culminating in a really quite surprising and gory propellor death for the arch villain.
Would It Work In Real Life? Every fibre of our being screams that no, there’s no way in hell this could ever...oh wait, what? Based on a true story, you say? Apparently yes, a pilot did fly a helicopter to a Mexican prison to rescue a man who claimed he’d been wrongly accused. So we guess it is actually a viable escape plan, though whether quite so many wigs, disguises, bouncing checks and duplicitous Mexicans were actually employed in the real attempt, we really do doubt.

Cool hand Luke

"Cool Hand Luke" (1967)
What's It About? The titular Luke (Paul Newman, in an iconic performance) is sent to a sweltering Florida prison after drunkenly cutting the heads off parking meters. It's here that he's sentenced to a chain gang, befriending Dragline (George Kennedy, who won an Oscar for his role) and annoying the fuck out of sadistic prison warden Captain (Strother Martin).
What's The Escape Plan: There are several, in fact. Early in the movie, Luke's ailing mother visits him in prison and later, when he learns that she has passed away, he attempts an escape so he can attend the services. He first attempts to flee during the cover of the Fourth of July celebrations, but is captured and fitted with leg irons. Following his capture, the warden makes the speech that gave the movie its famous "What we have here is a failure to communicate" line, warning the other prisoners of what would happen if they follow Luke's smart-ass lead. A little later, Luke escapes again, using an axe to remove his leg irons and spreading curry powder around to confuse the dogs. (During this escape Luke sends the prisoners a phony photo of him surrounded by two beautiful women—a classy touch.) He is, of course, recaptured and fitted with two sets of leg irons. After being forced to repeatedly dig and then fill in a grave-sized hole, Luke seems to have run out of will to live, except that he makes one last attempt, this time stealing a dump truck and driving to a nearby church (with Dragline). Dragline tells them that if they surrender peacefully, they won't be beaten, but a guard shoots Luke in the neck and Captain doesn't allow him to be taken to a nearby hospital, instead insisting that he be returned to the prison doctor. This doesn't end well.
How Successful Is It? It says something that Luke kept getting away, if only for a little while, but ultimately Luke gets shot in the neck, which we would definitely have to jot down in the "unsuccessful" column. 
Would It Work In Real Life? Again, we're not sure how a prison in the '40s operated, but it's hard to think of anyone surviving any of these escape attempts, if only because of the harsh surrounding conditions (especially at that time). Walking around Florida's Disney World in 2013 is taxing enough, we can't even imagine what it would be like to mount numerous prison break escape attempts.

rescue dawn

Rescue Dawn” (2006)
What's It About? Based on his own documentary “Little Dieter Needs to Fly,” Werner Herzog’s contribution to the prison break genre is an unsparing, heart-of-darkness, maggot-eating look at the capture of Dieter Dengler (Christian Bale), a pilot for the US Navy, in Laos, during the Vietnam War. Once imprisoned, Dieter has to overcome the institutionalization of his fellow inmates, some of whom have been kept in the camp, mistreated, malnourished and tortured, for years, and lead them all in a daring escape.
What's the Escape Plan: A mixture of seat-of-the-pants opportunism, long term planning in the squirrelling away of the paltry bare-minimum supplies and complete ruthlessness when it comes to the killing of the camp guards, the escape here feels organic, messy and totally plausible. When the majority of the guards are absent and the remainder are eating lunch, Dieter slips through a hole in the floor and crawls beneath the stilted huts to steal their guns. The plan is then to take whatever food, clothing and supplies they can find and make off into the jungle for the Mekong river which they can follow or raft down to Thailand and eventual rescue.
How Successful Is It? Bearing in mind that the escapees are actually let down by one of their own early on and the other inmates scatter to the four winds, leaving just Dieter and his friend Martin (Steve Zahn) to brave the surrounding jungle alone, the actual getting-out-of-the-camp part does in fact work. However the pair are then forced to try and fight their way out of the bigger prison of the unforgiving jungle and its sometimes antagonistic inhabitants and in the end never actually make it anywhere near the river.
Would It Work In Real Life? Again, this is based on a true story, so it kind of did work in real life, although whether the return of one man out of many can be considered “working” is up for debate (in fact one other real-life escapee was also rescued, but none of the others were ever seen again). There have also been questions raised about the film’s fidelity to actual events, particularly as regards the characterization of some of Dengler’s fellow prisoners, which differs considerably even from Dengler’s own account. However Dengler’s indomitable spirit, played in off-kilter fashion by Bale almost as a man on the edge of insanity, did indeed carry him home eventually, even if his story went untold for a long time after, due to the covert nature of his mission.