a man escaped

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 Guy Pearce

"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

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

"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.