Escape from NY

"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

“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

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, Nicolas Cage

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?