1. Escaped Three Times by Helicopter
Pascal Payet was initially sentenced to 30 years in 2001 for murder during an armored car robbery. Facing the prospect of spending his best years in prison, he devised an ingenious escape method: using a helicopter.
He managed to escape by helicopter three times. The first time was in 2001, when he figured out the prison helicopter’s schedule and hitched a ride out. In 2003, he used the same trick to fly back into prison and rescue three accomplices. His final escape was in July 2007, when three armed men hijacked a helicopter, flew to the prison in Cannes, and whisked Payet away once more. 
2. Escaped with a Fake Gun Made of Wood and Shoe Polish
John Dillinger, notorious for robbing at least 24 banks and four police stations in the 1930s, was captured but escaped in 1933 with the help of his gang, the “Dillinger Gang,” who posed as law enforcement. However, he was arrested again in 1934.
In March of that year, Dillinger crafted a fake gun from wood, coated in shoe polish, to escape. He tricked a guard into opening his cell, then took two hostages and locked all the guards in the cells, before driving off in a police car. Four months later, he was killed in a shootout during a capture attempt.
3. Locked Guards in the Bathroom to Escape
British national Alfred Hinds was arrested in 1953 for a £90,000 jewel heist. Despite pleading not guilty, he was sentenced to 12 years. He escaped from prison through locked gates and 20-foot-high walls, earning him the nickname “Houdini” Hinds.
In 1956, after being recaptured, Hinds sued the prison authorities for illegal arrest. He had a padlock smuggled in, which he used during a court visit to lock the guards in the bathroom. He then disappeared into the crowd on Fleet Street but was caught five hours later at an airport.
4. Escaped by Hiding Under a Car
In 2009, 39-year-old British man Julien Chautard was sentenced to 7 years for arson. Just days into his sentence, he mysteriously vanished on March 27, 2009. It took the police three days to realize he was gone, and they found no signs of a break-in or inside help.
On March 30, Chautard called the police to turn himself in, not to taunt them but because his family in France urged him to surrender. How he escaped remains unclear, but it’s believed he hid under a delivery van during yard time and rode it out of the prison.
5. The Only Man to Escape from Alcatraz
Alcatraz, known as “The Rock,” was thought to be inescapable. There were 14 escape attempts involving 36 prisoners. Of those, 23 were recaptured, 6 were shot, 2 drowned, and 3 remain missing.
On June 11, 1962, three inmates executed one of the most complex escapes ever recorded. They spent a year digging a hole through the concrete wall of their cell, using wet newspaper to create a fake wall. They made dummy heads from paper mâché to fool the guards, then escaped through the ventilation ducts, climbed up 30 feet, and down 50 feet to a makeshift raft made from raincoats. The FBI believes they drowned, but their bodies were never found, and they are still listed as fugitives.
6. Escaped to Become a Writer
Billy Hayes, an American, was sentenced to life in Turkey for drug smuggling in 1970. He planned his escape over six months, observing the prison routine. He knocked out a guard, donned his uniform, stole a prison boat, and escaped during a stormy night, eventually reaching Greece.
Back in the U.S., Hayes wrote a bestselling book based on his experiences, which was later adapted into the Oscar-winning screenplay “Midnight Express.”
7. Knocked Out One Guard After Another
On December 13, 2000, “The Texas Seven” escaped from John B. Connally Unit in Texas. They used a simple distraction technique, calling out “Hey! Look over there!” to knock out the supervising officer.
The comedy of errors continued as each guard or inmate entering the repair room was knocked out with the same trick. They incapacitated 9 guards, 4 officers, and 3 unsuspecting inmates, stole their clothes, credit cards, and IDs, and made off with prison weapons in a stolen van.
8. The Most Famous and Successful Escape During the Civil War
The Libby Prison Escape is one of the most famous and successful escapes during the American Civil War. Between February 9 and 10, 1864, over 100 Union soldiers escaped from Libby Prison in Richmond, Virginia.
They dug a tunnel from the basement, breaking through to a nearby warehouse’s tobacco shed. Out of 109 escapees, 59 made it to Union lines, 48 were recaptured, and 2 drowned in the nearby James River. The escape was masterminded by Colonel Rose and Major Hamilton.
9. Escaped from Auschwitz
Rudolf Vrba and Alfred Wetzler were among the few to escape from Auschwitz. On April 7, 1944, with the help of the local resistance, they used tobacco soaked in gasoline to fool the guard dogs, cut through the wire, and escaped towards the Polish-Slovakian border.
Their report on the atrocities at Auschwitz, including details of gas chambers and crematoria, was recognized by the Allies and helped save 120,000 lives.
10. The Only American Pilot to Escape from a POW Camp in Vietnam
Christian Bale starred in the 2006 film “Rescue Dawn,” which tells the true story of American pilot Dieter Dengler’s escape from a POW camp in Vietnam.
In early 1966, Dengler’s plane was shot down over Laos, and he was captured. On June 29, 1966, he and six other prisoners managed to overpower their guards and escape. After 23 grueling days in the jungle, only Dengler and one Thai prisoner survived. He was the only American pilot to escape during the Vietnam War.
