Four men conspire to break out of one of the most notorious prisons in American history. Three make it to the water's edge... but what happened to them when they left the island remains a mystery to this day.

Stuck in prison on life sentences, two men used engineering smarts and psychological manipulation of several prison employees to escape Dannemora Prison; Richard Matt and David Sweat executed one of the most involved escapes from an American prison.

Six men, led by the mastermind, Nuno Pontes, escaped Pittsburgh State Penitentiary by tunneling to freedom under the massive wall of the prison. They made it as far as Texas before being caught and returned to prison.

Allied prisoners used all kinds of forgery and engineering tactics to tunnel out of a German Prisoner of War camp. Almost all were caught, fifty were executed and three made their way to freedom.

Almost forty prisoners locked up in HM Maze prison for actions undertaken as members of the IRA, escaped in a food truck. Many were caught right away, some years later, and some were never seen again.

Timothy Vail and Timothy Morgan were murderers incarcerated at Elmira State Prison in Elmira, N.Y.;. Vail wanted to escape, so he engaged Morgan in his plan to dig through the ceiling and flee from prison.

James Earl Ray, confessed killer of MLK, was a notorious escape artist. His most audacious escape involved manufacturing a ladder made of plumbing pipe and going over the wall of the Brushy Mountain State Prison.