Our 15 Favorite Prison Breaks At The Movies

“You’ll like it, it’s about a prison break” says Andy Dufresne in “The Shawshank Redemption” about the book they’re shelving, Alexander Dumas’ “The Count of Monte Cristo.” “We oughta file that under ‘educational’ too, oughtn’t we?” quips Red in reply, and indeed, with the sheer number of prison escape books and movies that exist, you’d imagine that all a really dedicated inmate has to do is watch or read enough of them before they’d stumble across a plot that could be adapted for their own situation. (Note: The Playlist does not condone real-life attempts at fleeing prison unless you’re totally innocent, a prisoner of war or you have a really cool plan that involves disguises and dummies and stuff.) This week a movie in a similar vein is released and we highly doubt it will be accused of having any educational content whatsoever: “Escape Plan.” Starring brawny side of aged beef Sylvester Stallone and tanned leather pommel horse Arnold Schwarzenegger, the film puts “the world’s foremost authority on structural security” (that’s a thing?) into the “world’s most top-secret escape-proof prison” (also a thing?) and has him team up with his cellmate to devise an exit strategy while also finding out who framed him and why.

While this film (previously titled “The Tomb”) may look dumber than a bucket of hair, and has been strangely un-buzzy despite its starry cast (Jim Caviezel, 50 Cent, Vincent D’Onofrio, Vinnie Jones and Amy Ryan also appear), we’re fully prepared to accept that it’s could be a lot of fun in a brainless, unreconstructed way, mainly because as often-visited as the territory may be, we have kind of a weakness for prison break films, even when they’re ever so silly. Perhaps it’s something metaphorical about anti-authoritarianism and sticking it to the man or perhaps we’ve killed a bunch of people (watch those critical comments guys!) and realize it’s just a matter of time before we’re caught and incarcerated ourselves. Whatever the truth is here’s a jolly good sampler of 15 of our arbitrarily chosen favorite movie prison breaks, and what we might be able to learn from them. Be warned, though, since we’re talking about the success or failure of the schemes, here be *SPOILERS* throughout.

"Escape to Victory" (1981)
What’s It About? Angling for a propaganda stunt, German POW camp commandant (Max von Sydow) arranges an exhibition soccer match between a team of Allied prisoners, and a German team made up of Wehrmacht officers. While the Allied coach (Michael Caine) resists attempts to use the match as a cover for an escape attempt by the team (populated with real-life famous footballers like Bobby Moore and Pele), an ornery American, Hatch (Sylvester Stallone), working in tandem with the Resistance, ignores the coach and plots to do just that.
What’s the Escape Plan? Noting that the Colombes stadium in which the showcase match is to be held is adjacent to the Paris sewer system, the Resistance decides to tunnel into the Allied team’s dressing room, and smuggle them out from there.
How Successful Is It? Actually it’s a complete success, with the tunnelers breaking through at half time when the team, at this point being beaten 4-1 due largely to deeply biased refereeing and foul play by the Germans, is resting between halves. However their recognition of the moral victory that is at stake is such that they elect to return to the pitch instead of escaping, whereupon their pluck results in a magnificent draw that spurs an ecstatic (and very early 80s-looking) crowd to invade the pitch, and they escape in the throng anyway. Even crusty old Max von Sydow appears to have been won over by the sportsmanship he’s witnessed and doesn’t lift a finger to stop them leaving.
Would It Work In Real Life? Probably not, considering how many variables there are, not to mention requiring an escapee to allow himself to get caught again in order to communicate the plan in the first place.In fact the film is based on a real-life event albeit one that didn’t end in quite such a "football conquers all" victory as here, nor one that actually featured an escape attempt. The 1942 "Death Match" as it was nicknamed, became the subject of Soviet propaganda after the fact so details are fuzzy, but it was apparently the last in a series of matches played between a team of Ukrainian professional footballers and a team representing the occupying Germans. The Ukrainians had won every one of their matches and had become a popular draw, and this last match was no exception. Afterwards, however several members of the Ukrainian team were arrested and persecuted by the Gestapo, resulting in their deaths, while still others remained free only to later be prosecuted as German agents by the Soviets. So, a much messier true story, and one in which Sylvester Stallone never got in goal, but still it would appear that here too, the love of the game drove the players never to capitulate, at least not on the pitch.

"Chicken Run" (2000)
What’s It About? A bunch of chickens, realizing they’re next for the chopping block (after the farmers go from selling eggs to chicken pot pies), plan an escape from their oppressors.
What’s The Escape Plan: "Chicken Run" is loosely based on "Stalag 17," with Mel Gibson playing a cocky rooster named Rocky who promises to teach the chicken how to fly in order to escape the farm. It’s discovered, of course, that Rocky isn’t who he says he is and he "flew" by getting fired out of the canon (he is a circus performer, but had a history as a pilot). After a period of depression, the birds decide to build a plane out of parts made from the chicken coops (they have access to old airplane schematics) and have Rocky pilot the plane. It’s pretty cute.
How Successful Is It? Not only do the chickens escape to freedom in their makeshift airplane, but they also destroy the machine that the farmers are planning to use to artificially fatten the chickens. At the end of the movie, the chickens have established a kind of chicken safe haven for themselves, where they can live and work and breed in relative peace. Again: it’s pretty cute.
Would It Work In Real Life? Although no scientific tests have been conducted, if a bunch of chickens were left with some airplane schematics, chicken coop parts, and a will to live, they probably would be able to pull something like this off. While "Chicken Run" is an animated film (by the stop motion geniuses at Aardman) for children, the movie often plays up occasionally haunting imagery held over from the World War II internment camps, which doesn’t lessen the real life tragedy but imbues this animated film with an eerie sort of history. You know, it’s pretty cute.

“The Escapist” (2008)
What’s It About? Rupert Wyatt’s underrated, oddly rhythmed debut feature, which was well received at Sundance but failed to find much traction after, stars Brian Cox as Frank Perry, an institutionalized lifer who only decides to attempt an escape 14 years into his stretch when he discovers his daughter is addicted to drugs. Collecting a gang of accomplices around him, he puts his plan into action, but is compromised by his cellmate (Dominic Cooper) getting mixed up with the prison ganglord (Damian Lewis). The final act twist does take some acrobatics and many may find themselves already frustrated by that point, but it’s still an ambitious attempt to do something different with a well-worn genre.
What’s the Escape Plan: The film jumps between two narrative timeframes, meaning it’s hard to get a coherent picture of the exact procedure of the escape, however it involves a lot of clambering through holes in walls, and some torchlit processions through disused London Underground tunnels, and, at one point, gasmasks. That there is a narrative reason for the impressionistic nature of the escape is only gradually revealed, though whether that revelation totally justifies the self-consciously non-linear approach is debatable.
How Successful Is It? Spoiler alert or no, this is a film we don’t want to wholly give away because of the likelihood of not so many people having seen it. So suffice to say,from Frank’s point of view, it’s a successful attempt, though his matrix for judging success gets progressively more complex as the film goes on.
Would It Work In Real Life? Ha, well, let’s see, no, probably not. Not only is the plan poetically rather than practically laid out within the film, it is as far as we can tell, almost impossible to have arranged the practicalities of the escape without detection. And it’s also heavily implied that it needs a pretty spectacular diversion to work at all—and the diversion is not, in fact, part of the plan. Which will all make more sense if you’ve seen it, if only a little.

“A Man Escaped” (1956)
What’s It About? A resistance fighter caught by the Nazis and eventually sentenced to death whiles away the hours by meticulously planning his eventual escape, while trying to communicate with the man in the neighboring cell and his other fellow inmates. (You can read about Robert Bresson’s masterpiece in more depth here and here).
What’s the Escape Plan: Having spent painstaking hours, days and weeks carving away at his cell door with a spoon to enable him to remove the panels and make an opening large enough to slip through, Fontaine (Francois Leterrier) makes ropes and hooks out of the few furnishings of his cell—his mattress, his ventilation duct, his bedsprings—but has to improvise further when a cellmate is billeted on him and he’s forced to let him in on the plan. One of the great strengths of the film is in conveying just how difficult it is, however, despite all the preparation and planning, to actually make the decision that tonight’s the night.
How Successful Is It? After an unbelievably tense night, during which a guard is killed and Fontaine’s patience and knack for noiselessness are again shown to be his greatest assets, he and his accomplice both make it over that last wall and walk across a bridge to freedom, albeit without the jackets and shoes they accidentally left on the roof.
Would It Work In Real Life? Apparently, incredibly, it did. Director Robert Bresson opens the film a title testifying to its absolute veracity, and the film adheres closely to the real story of Andre Devigny, who escaped imprisonment in Fort Montluc during World War II. Quite aside from the bravery and the ruthlessness needed, the diligence, inventiveness and oceans of patience that this escape required just boggle the mind. An amazing story of an amazing man that, for once, has full justice done to him in an amazing movie.

"Lockout" (2012)
What’s It About? It’s set in the distant future, on a floating prison colony (in outer space!), where the Vice President’s daughter (Maggie Grace) has agreed to take a tour of the facilities, which has many of the criminals locked in a kind of suspended animation. Of course, while she’s there a whole bunch of things go wrong and the president enlists the help of a wrongly accused good-guy scumbag (Guy Pearce) to rescue her from all of the bad guy scumbags, who fortunately haven’t yet discovered her real identity and value. Yet.
What’s The Escape Plan: Pearce’s character, Snow, isn’t a man with a plan as much as a man who wants to do the job and maybe save his own ass along the way (the Snake Plissken school of…everything). In that way of thinking, he plans on meeting up with his ex partner, Mace, who has information that can clear his name back on earth. So he finds the president’s daughter and disguises her as one of the prisoners, changing her hair to blend in, and guides her to an escape pod, which is necessary because the prisoners have killed all of the personnel on the prison colony, leading it to fall out of orbit and crash into a space station (d’oh!) But his plan, such as it is goes awry when Snow reaches the pod and realizes there is only room for one…
How Successful Is It? The two expose some dirty goings on involving the prisoners, find some space suits and fall to earth as the space prison explodes behind them and is obliterated, so 100% mission accomplished, we guess!
Would It Work In Real Life? There are a bunch of huge leaps in logic to even make "Lockout" work as a movie, much less a blueprint for an actual, real-life escape. This is especially true considering that the movie takes place in outer space, on a floating prison colony and at one point Pearce blows up a guy’s head using some kind of explosive dog collar. That part was pretty cool. That said, when the future arrives and orbital prison systems are a real thing (or maybe one on the moon, like in "Men in Black III"), maybe this will all seem like the height of gritty realism, though note to future prison architects: please design the escape pods to seat a minimum of two.

“Escape from Alcatraz” (1979)
What’s It About? A Don Siegel-directed dramatization of what may have been the only ever successful escape from the notorious island prison, “Escape From Alcatraz” follows prisoner Morris (Clint Eastwood) as he is first incarcerated, and then experiences the hardships of prison life, both from the guards and his fellow inmates. Morris hits on a long-term plan for escape, and after a series of incidents that demonstrate the inhumanity of the situation in Alcatraz, he, his neighbor and the two Anglin brothers (Fred Ward and Jack Thibeau) put it into action in earnest.
What’s the Escape Plan: Discovering that the cement around the ventilation grilles in the cells is old and crumbling, Morris fashions a digging tool out of spoons and, over the course of a year, the men work away, eventually each creating a hole big enough to squeeze through. Leaving papier mache heads in their beds to fool the guards, the men escape onto the roof and off the island using a raft they’ve fashioned from raincoats.
How Successful Is It? In the film all three who attempt the escape (Morris’ neighbour loses his nerve at the last moment and stays behind) are strongly implied to have made it to Angel Island and freedom beyond, though the warden (Patrick McGoohan) insists that they drowned in the attempt.
Would It Work In Real Life? Well there’s still no definitive answer to the question, as neither the living men nor their bodies were ever found thereafter. However as regards simply evading detection and getting off the island, that certainly did happen, and though the FBI’s official conclusion at the time was that they must have drowned, the remnants of the makeshift raft was found on Angel Island, and recent investigations suggest they may in fact have made it there. However, with the number of thwarted escape attempts previously (at least 13, with one other attempt’s outcome still not definitive due (again) to not finding the bodies) we’d have to say the odds of a repeat success with this method would have been zero, and besides which, the point is moot: Alcatraz closed the year after this escape attempt. Still, probably slightly more plausible than the Alcatraz escape effected in Michael Bay‘s finest hour "The Rock."

"The Shawshank Redemption" (1994)
What’s It About? In Frank Darabont‘s adaptation of the beloved, horror-free Stephen King novella, a man who is wrongly accused of a murder (Tim Robbins) befriends an old timer (Morgan Freeman) and secretly plots his escape from the ruthlessly ruled Depression-era prison.
What’s The Escape Plan: One of the more amazing things about Darabont’s film is that the escape isn’t the central focus of the movie, instead it’s the friendship between the two men. In fact, the entire escape comes as something of a late-in-the-game surprise and it’s only explained after Robbins escapes. It involves Robbins burrowing out from his cell (using the some of the same techniques employed in "The Great Escape," including the old "shaking the dirt out of your pant leg" routine) and covering up his escape using a cheesecake poster of Rita Hayworth, then Marilyn Monroe, then Raquel Welch (the original name of the novella was "Rita Hayworth and the Shawshank Redemption"). He then travels through an endless sewer system to emerge into the real world again (that moment provides the movie with its iconic "rebirth through rain" shot, where Robbins embraces the rain that washes over his shit-covered body).
How Successful Is It? Robbins gets out and goes to live on a beach, waiting for his friend to join him, which makes it probably the most successful (if also one of the most long-term and laborious) escapes in movie history.
Would It Work In Real Life? We’re pretty iffy on the Depression-era prison system’s security, and while the movie points out how arduous Robbins’ journey is, it still seems kind of easy, if requiring almost superhuman patience, discretion and foresight. You just need a rock hammer, a poster and nearly two decades of spare time.

"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" (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” (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.

"Escape from New York" (1981)
What’s It About? In the future (1997!), New York has been turned into a prison colony. A plane carrying the president crashes onto New York City. The only person who can get the President out alive is the worst criminal ever—Kurt Russell‘s eyepatch-wearing, acid wash-jeans-loving Snake Plissken. To up the ante, of course, Plissken has been injected with an explosive device that will kill him in a matter of hours unless he brings the president back alive. So that means he can’t fuck off or kill the president (he’s also got a secret tape that is vastly important—please keep in mind that this was conceived right after Watergate, though what it actually says about that scandal is anyone’s guess).
What’s The Escape Plan? Snake has to rescue the president from The Duke (Isaac Hayes) and escape all the warlords, criminals, and terrorists infesting the island. Snake isn’t exactly the bookish "escape plan" type of guy, so his adventure includes, amongst other things, gliding from the top of the World Trade Center and driving a runaway cab across a bridge littered with explosives. Finally, he makes his way to the fence surrounding the island and the president is lifted over it. Many of these same beats are repeated in the ill-fated (but still hugely enjoyable) "Escape from L.A."
How Successful It Is? "Escape From New York" is incredibly pessimistic, so even though the president makes it to safety and Snake Plissken lives to tell the tale (he’s offered a pardon and walks away), there is still one last fuck you: the tape that was so important to both the President and the country has been switched, last minute, by Snake, with a recording of "Bandstand Boogie." Snake, the ultimate anti-authoritarian figure, destroys the tape, his metaphoric middle finger raised high.
Would It Work In Real Life? Er, considering "Escape from New York" is a fantastical work of science fiction, none of this would have worked in real life (most likely), and not just because the World Trade Center isn’t standing (although it was in 1997). The fact is, that though we’d like to believe there’s a little eyepatch-wearing antihero in all of us, it’s hard to see anyone but Plissken prevailing here. So as a blueprint for an escape from a criminal-infested island, it’s lacking, but for pure thrills, it’s a riot.

“Two Way Stretch” (1960)
What’s It About? A typical British caper comedy, typically starring Peter Sellers and Bernard Cribbins, ‘Stretch’ tells of the high-spirited hi-jinks of unrepentant inmate Dodger Lane (Sellers) who breaks out of the prison in which he’s quite comfortably ensconced, to commit a diamond heist. Then he breaks back in, thereby establishing for himself and his gang the perfect alibi.
What’s the Escape Plan: While at first it seems, given Lane’s privileged standing within Huntleigh prison and his good relations with jovial guard Jenkins, that popping out for a few hours won’t be a problem, that scenario changes with the arrival of tough new screw Crout (Lionel Jeffries). In a nice meta moment, the escape/reentry plan subsequently mooted by Lane is inspired by “The Wooden Horse” (see above) and involves a hollow vaulting horse. Next up comes a wheeze based on 1959’s “Danger from Within” which also comes up short, until finally Lane arranges, via carrier pigeon traffic with his girlfriend, Cribbin’s mother and the gang mastermind (Wilfrid Hyde-White), to leave in a fake Black Maria police van and return via a garbage truck.
How Successful Is It? Goes smooth as silk it does, as does the heist of the Sultan’s diamonds, before the gang is released a day later having served out their sentences, and all that’s left is the simple, straightforward and in no-way-destined-to-foul-up business of retrieving the diamonds.
Would It Work In Real Life? We don’t see why not, provided you’ve the good fortune to be sent down to one of those terrifically genial British prisons in which the wardens are well-meaning, marrow-growing dimwits, the guards are eternally distracted by a glimpse of comely thigh and the only vigilant screw is the constant recipient of slapstick come-uppance. But while the film may be slight and pretty forgettable in the scheme of things, it does deserve some plaudits for inspiring beloved Brit sitcom “Porridge.”

“The Wooden Horse” (1951)
What’s It About? Another based-in-truth story, and one actually set in the very same POW camp that originated “The Great Escape,” “The Wooden Horse” stars Anthony Steel, David Tomlinson and the ever-urbane Leo Genn as three British prisoners who tunnel to freedom using a vaulting horse in the exercise yard as cover. The film’s low budget and often amateur cast actually give it more of a feel of authenticity than many similar films, even if it falls quite far short of the glossy greatness of its better-known brother.
What’s the Escape Plan: Realizing that their accommodation huts lie too far from the perimeter fence to allow them to tunnel from them, the escape leaders build a vaulting horse from old Red Cross parcels, and recruit other inmates to practise with it, as though they’re training a vaulting team. In fact, the horse, like that of Troy, conceals a man who, once it’s set down in the yard near the fence, tunnels through the ground a little further each day, before covering up the tunnel entrance and concealing himself and the displaced earth. When the tunnel is completed the three use it to escape, and once out, split up before reuniting in Sweden.
How Successful Is It? As a cheery counterpoint to “The Great Escape,” all three actually do get clean away, and thanks to much assistance along the way, make it to neutral Sweden and are home in England by Christmas.
Would It Work In Real Life? Again, as impossible as it seems and as totally dreamed-up-by-Hollywood as the plan might appear, the broad details here did actually occur: the vaulting horse, the training cover, the tunnel, the successful escape and return of the three POWs. And the film’s somewhat plodding pace and prosaic tone actually make it easier to believe than you might think.

“Con Air” (1997)
What’s It About? Cameron Poe (Nicolas Cage) somehow has the dumb luck to be on his way home on parole aboard a plane that is otherwise stacked to the overhead compartments with the most dangerous criminals, seemingly on the whole of planet Earth. When, led by Cyrus (John Malkovich) the murderers, rapists, paedophiles and serial killers take over the plane and reroute it so they can escape, Poe must try to stop them even though FBI people on the ground regard him as an enemy too. One of the funnest and dumbest films ever to be described as “dumb fun.”
What’s the Escape Plan: Allowing the plane to continue on its intended route for a while, Cyrus masterminds the offloading of the pilot and guards dressed as prisoners and switches the plane’s transponder with that of another plane, so that the authorities (represented by a pompous Colm Meaney and a dedicated John Cusack) follow the wrong plane for a time. Enough time for them to get to a different airfield where one of the high-profile prisoners has promised to have another plane waiting and ready to take them all to a non-extradition treaty country.
How Successful Is It? It really doesn’t work out at all well, and not just because the “brilliant” Cyrus doesn’t cop to Poe’s secret “good guy” agenda until quite a bit of harm’s been done, but also because he makes the fatal mistake of forgetting that the incorrigible criminals he’s journeying with are not the most trustworthy of individuals. So he’s doublecrossed at every turn but still manages to stagger on through the power of sheer malevolence and ludicrous plot devices until, having crashed landed into a Vegas casino, it again falls to Poe to hunt him down, finally seeing him crushed to death in one of those industrial pounding machines that’s only conceivable purpose is to kill unkillable movie supervillains.
Would It Work In Real Life? No. To be honest "real life" and "Con Air" are completely unrelated concepts. Like chalk and schadenfreude.

There are a gazillion prison break films, of course, ranging from all-out comedies (“The Parole Officer,” “Lucky Break,” “Stir Crazy” “O Brother Where Art Thou?” among others) to gritty dramas (“Papillon,” “Midnight Express,” “Brute Force,” “Runaway Train” “The Defiant Ones,” “Lonely are the Brave” to name just a few) and hitting all points in between. And no doubt you’ll have your favorites that we missed out so feel free to shout them out in the comments below especially if there’s one that you feel boasts a particularly ingenious and/or foolproof plan. You never know, right?