5 Most Daring Real-Life Prison Breaks

For most of us the rule of law is rather straightforward: Don't break it and you won't get in trouble. For others it's not so simple. Some break the law to enrich themselves and fulfil a need for adrenaline, others do it out of desperation and a few are brave souls who risk imprisonment due to their political viewpoints in highly censored nations. Whatever the case, they usually end up in prison.

Human nature being what it is, innocent or not every inmate suffers in the unforgiving environment. So, ever since the punitive measure of imprisonment has existed, humans have been using whiley means for attempting to escape. More often than not, it's almost impossible to achieve, requiring tireless organization, serious courage and lots of luck. Prison breaks have fascinated the public for centuries; as most escaped cons are dangerous criminals, it's likely the bad odds battled by these people that wins them admirers. Whatever the case, prison breaks have had the knack to catapult criminals from obscurity to infamy overnight. Below, we're exploring a range of fascinating prison breaks; their methods, the escapees and the end result. Were the cunning perps killed, captured or are they still free? Stay tuned.

5 Henri Charrière's Escape

Henri Charrière's life was immortalized in Steve McQueen's adaptation of his life in the 1973 movie Papillon.  Henri Charrière started out as minor criminal in the Paris underworld before being accused and convicted for the murder of a pimp in 1931. A charge he strenuously denied. First he served some time in a prison in France before being shipped of to French Guyana to serve in the brutal conditions of the prison labor camp in South America. While there Charrière was involved in numerous escape attempts most of them ending in failure. The more he tried to escape, the more punishment he received, up to a point where he was in solitary for months on end. Realizing his escape attempts were futile, Charrière feigned insanity so as to be sent to an island where security was lax. Despite this charade he was captured again and "cured" of his insanity. A one last ditch gamble finally paid off for him when he volunteered to be an inmate at Devil's Island, the least accessible prison Island. This Island was so remote that the prisoners were not regularly guarded, this allowed Henri to devise a plan to escape by laying on top a sack of coconuts and allowing the current to take him out to sea. It was a successful escape and Charrière settled down in Venezuela, free from French authorities.

4 Mountjoy Prison Helicopter Escape

The Mountjoy Prison in Dublin, Ireland was known to be a tough place to break out of. So when three high ranking Provisional Irish Republican Army commanders decided they'd had enough of prison life....they didn't exactly take the more traditional routes of escape. A previous attempt had been made by their comrades in arms to liberate them out of the prison that involved smuggling in dynamite and having a van nearby ready when the inmates tore a hole in the prison's exercise yard wall.

That plan was foiled when the IRA inmates had failed to secure access to the exercise yard that day and a rope on the prison wall was seen by the guards. Not to be deterred, the IRA devised another even more over the top plan to have their buddies out on the streets and fighting the British occupation. They hijacked a helicopter and at gunpoint told the pilot to land on the prison's exercise yard. Caught completely unawares the prison guards response was tepid at best and the the three IRA commanders got on the helicopter and flew away. In the aftermath there was political hell to pay as the whole encounter was embarrassing for the government of Ireland and Britain. All three inmates were eventually recaptured and sent back to prison with added years to their sentences for escaping.

3 Chicago High Rise Prison Escape

This is a relatively new prison break and it made the headlines when it occurred some two years ago. Jose Banks and Kenneth Conley were two convicted bank robbers serving time in the world's only skyscraper prison in Chicago, Illinois. On the night of December 17th, 2012 they turned out to be missing from their cells during morning head count. It so turned out that the cellmates had broken the window of their cell and sawed off the metal bars before making their escape via a rope made from bed sheets. Classic huh? Well while the escape in and of itself was brilliant and eye catching what the cellmates did afterwards was not.

They simply hung around the Chicago area and were eventually caught. Quite baffling seeing as to the fact that they had over $600,000 dollars in their possession. I'm guessing they didn't have the right networking to get themselves some quality fake identities with the kind of cash they were sporting. What's a decent forged passport cost? $10,000 for each man? Then off to a non extradition country and they're home free. OK, maybe I'm over simplifying things here. Nonetheless their capture just goes to show breaking from prison is more than just making it past the walls and the guards. It gets harder on the outside.

2 The Great Escape-Stalag Luft III

This latest prison break is arguably one of the most daring and meticulously planned ones to date. During WWII many a British and American pilot found himself shot down over Nazi Germany and become a POW. Ironically enough the Nazis held American and British POW's in high regard, given their racial policies favoring Anglo-Saxon nations. Due to this most of the downed pilots were interned in Luftwaffe or German air force prison camps. The latter had a reputation of civility and treating their prisoners well, unlike their SS and Gestapo counterparts.

Taking advantage of this "hospitality", British and American airmen devised a massive prison break to wreck havoc on the German home front, draining Nazi resources to find the escaped prisoners, diverting them from the war effort. They began their work in 1943 and by March 1944 several tunnels had been dug for the escape. Although there was some 600 Allied POW's in the camp, only about 200 could escape due to time constraints. Of these only 76 made it through the tunnel and into the woods surrounding the camp before a German guard noticed what was going on. Although the escape seemed initially successful all but three of the escapees were captured soon thereafter. The Gestapo then took cruel revenge on the escapees.....murdering 50 of them in cold blood as warning to future POW's and for the massive problems the 76 had created for the German home guard.

1 Escape From Alcatraz 1962

So far this is the only escape attempt from Alcatraz Island where the inmates were not apprehended afterwards or found dead in the harbor. Despite it being a prison on an Island the temptation for many inmates to escape across the bay to San Francisco only a mere couple of miles away was too hard to resist. Easier said than done. Even if you could get out of the cell and even outside the prison perimeter swimming the bay was treacherous. Hypothermia would set in within minutes and the current was too strong. Yet on the night of June 11th, 1962 that's what three prisoners actually did. The brothers Clarence and John Anglin along with Frank Morris all career criminals with violent convictions on their names escaped from Alcatraz Prison. A fourth man, Allen West, could not make it as he failed to get out of his cell in time to join the others and was left behind.

The inmates had set up an elaborate escape plan using prison tools to their advantage. Spoons and forks were used to dig the decaying, molding wall on their air vent grills in their cells and then makeshift life preservers were made from prison raincoats so that they could swim across the harbor without overextending themselves. They left behind dummy heads to fool the guards patrolling the cell block at night. Although the official FBI report says the men most likely drowned, thus far their bodies have never been recovered.


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