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.

El Chapo became one of the most notorious and murderous drug cartel kingpins in modern history. His audacious escapes from maximum-security prisons in Mexico became the stuff of legends. He is now in a US supermax prison in Colorado where he is remanded to this day.

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.

A lone wolf prisoner, with aspirations of writing crime novels, ends up the star of his own break out story when he figures out how to escape from one of Mississippi's oldest and most notorious prison farms, Parchman Penitentiary.

A German American pilot, Dieter Dengler, uses survival skills honed as a child to escape a secret prison in Laos during the early years of the Vietnam war.

A lifelong escape artist, Forrest Tucker, ends up in San Quentin prison; despite his advanced age, he manages to engineer an audacious prison break.

Interviews and re-creations bring some of history's most daring jailbreaks to life, detailing every step of the way, including the inmates' meticulous plans and the manhunts that followed.

Interviews and re-creations bring some of history's most daring jailbreaks to life, detailing every step of the way, including the inmates' meticulous plans and the manhunts that followed.

Quawntay Adams, a young African American man from Los Angeles gets caught up in a large-scale marijuana bust and is sentenced to a long prison term; when he finds out he is going to be a father, he determines to break out of his cell.

During the Civil War, a daring prison break frees hundreds of captured Union soldiers; Colonel Thomas Rose was a schoolteacher before the Civil War; when he was captured and sent to Libby Prison in Richmond Virginia, he engineers a mass escape.

An Iranian-American psychopath goes to the men's city jail in Orange County Jail in Southern California; before he gets sent to a higher security prison, he escapes by crawling up the plumbing chase and rappelling down the side of the prison.