1Pascal Payet: escaped from jail using a helicopter three times!
2John Dillinger: escaped from jail using a fake gun made of wood and shoe polish
On March 3, 1934, Dillinger escaped from the "escape-proof" (as it was dubbed by local authorities at the time) Crown Point, Indiana county jail, which was guarded by many police officers and national guardsmen. Newspapers reported that Dillinger had escaped using a fake gun made out of wood blackened with shoe polish. With his fake gun he was able to trick a guard into opening his cell. He then took two men hostages, rounded up all the guards in jail, locked them in his cell, and fled. (Source)
3Alfie Hinds: escaped from jail three times, one of them by locking the guards in the bathroom
He made an honest living as a builder and decorator across Europe until 1956, when Scotland Yard detectives tracked him down and arrested him again after 248 days as a fugitive. After his arrest, Hinds brought a lawsuit against authorities charging the prison commissioners with illegal arrest and successfully used the incident as a means to plan his next escape at the Law Court. When two guards escorted him to the bathroom and removed his handcuffs so he could take care of business, Alfie shoved them into the stall and locked them with a padlock (accomplices had installed screw eyes onto the door so he could do this). He was captured at the airport only a few hours later.
His third escape was from his Chelmsford Prison. He then returned to Ireland where he lived and worked as a used car dealer for two years. His downfall came once again when he was pulled over for being in an unregistered car. This time, he used his smarts to find a loophole in the law – at the time, prison escapes were not considered misdemeanors, so no time was added onto his original sentence. He finished out the six years from his jewelry theft sentence in 1953, won a libel suit against the arresting officer, and spent the rest of his life as a minor celebrity after selling his life story to the News of the World for a reported $40,000. (Source 1 | Source 2)
4Julien Chautard: escaped from prison by clinging to the underside of the van that had just brought him there
5Frank Morris and Clarence and John Anglin: the only prisoners who may have escaped from Alcatraz
But on June 11, 1962, Frank Morris and John and Clarence Anglin successfully carried out one of the most intricate escapes ever devised. Morris and the Anglins climbed up the ventilation shaft through one of the chimneys and reached the top of the roof. The trio then climbed down the rooftop and paddled away on rubber rafts. The next morning police searched for the escapees on Alcatraz without success.
The acting warden said they put dummy heads - made of a mixture of soap, toilet paper and real hair - in their beds to fool prison officers making night-time inspections. Morris and the Anglin brothers subsequently disappeared without trace and are still wanted by the FBI, although they are believed to have drowned in the San Francisco Bay while attempting to leave the island. (Source)
6Billy Hayes: escaped from a Turkish prison and became a writer
7The Texas Seven group: escaped a maximum security prison using a highly elaborated scheme
The attackers stole clothing, credit cards, and identification from their victims. The group also impersonated prison officers on the phone and created false stories to ward off suspicion from authorities.
After that, three members of the group made their way to the back gate of the prison, some disguised in stolen civilian clothing. They pretended to be there to install video monitors. One guard at the gatehouse was subdued, and the trio raided the guard tower and stole numerous weapons. Meanwhile, the four offenders who stayed behind made calls to the prison tower guards to distract them. They then stole a prison maintenance pick-up truck, which they drove to the back gate of the prison, picked up their cohorts, and drove away from the prison.
A year later they were apprehended, as a direct result of the television show America's Most Wanted. (Source)
8The Rat Hell prisoners: the most famous (and successful) prison breaks during the American Civil War
The Libby Prison escape was possible thanks to the effort of its leaders, Colonel Rose and Major Hamilton. Rose and Hamilton worked tirelessly together to bring about the escape. It was Rose who thought of breaking into the basement from the chimney and Hamilton who engineered the passage. Rose toiled feverishly in the tunnel and organized digging teams while Hamilton worked out the logistics and invented contraptions for removing dirt and supplying oxygen to the tunnel. (Source | Photo)
9Alfred Wetzler and Rudolf Vrba: managed to escape from Auschwitz and later compiled a life saving report about the Nazi camp
On April 10, wearing Dutch suits, overcoats, and boots they had taken from the camp, they made their way south, walking parallel to the Soła river, heading for the Polish border with Slovakia 80 miles (133 km.) away, guiding themselves using a page from a child's atlas that Vrba had found in the warehouse.
Wetzler and Vrba later became known for the report they compiled about the inner workings of the Auschwitz camp – a ground plan of the camp, construction details of the gas chambers, crematoriums and, most convincingly, a label from a canister of Zyklon gas. The 32-page report was the first detailed report about Auschwitz to reach the West that the Allies regarded as credible. The report is said to have saved 120.000 lives. (Source)
10Dieter Dengler: became the only soldier to escape a prison camp during the Vietnam War
Note: We had first stated that he was the only American soldier to successfully escape from a prison camp during the Vietnam War. But our readers pointed out there were other heroes to do so, such as Capt. Charles Fredrick Klusmann, who was shot down, captured to escape later with 6 other inmates, 5 of which were never accounted for, and Nick Rowe, who escaped from a Viet Cong camp in Vietnam, and wrote a book about it called, "Five Years To Freedom." (Thanks, Katey and Josiah). (Source)