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CNN —  

Prisons are supposed to be the most difficult buildings to escape from. Yet inmates still break free – sometimes with dramatic helicopter stunts, sometimes just by slipping through the cracks (literally).

Here are some of the most bizarre prison breaks in history:

The chronic escapee

When Redoine Faid first escaped from prison five years ago, he blasted his way out with explosives.

The Frenchman was caught, locked up and given more time behind bars. He just escaped again – by hitching a ride Sunday on a hijacked helicopter.

Faid was serving 25 years in prison for his role in a failed 2010 robbery that resulted in the death of a French police officer.

He’s still on the loose after heavily armed accomplices hijacked a helicopter and forced the pilot to fly to Faid’s prison near Paris.

After picking Faid up, the armed men then forced the pilot to fly them to France’s Val d’Oise region before releasing the pilot unharmed and fleeing in an unidentified vehicle.

It was not immediately clear how Faid was able to get access to the hijacked helicopter.

The inmate who painted nectarines as weapons

Nadine Vaujour was so determined to get her husband out of a Parisian prison, she took helicopter flight lessons just for the escape.

Her husband, Michel Vaujour, was serving a lengthy sentence for attempted murder and armed robbery. In May 1986, the Chicago Tribune reported, Michel Vaujour “forced his way onto the prison’s roof by wielding nectarines that were painted to look like grenades.”

His wife then picked him up in a helicopter and whisked him away to a football field, where they landed and drove away.

But their luck soon ran out.

Nadine Vaujour was discovered and arrested in southwestern France. Michel was later shot in the head during a failed bank robbery, but survived.

The frequent flier

Apparently, helicopter escapes are popular among French inmates. And Pascal Payet didn’t flee into the sky just once – he did it three times, according to the Aircraft Owners and Pilots Association.

Pascal Payet escaped in a helicopter with another detainee in 2001.
Boris Horvat/AFP/Getty Images
Pascal Payet escaped in a helicopter with another detainee in 2001.

Payet first escaped from a Luynes prison via helicopter in 2001.

Two years later, while still a fugitive, he helped inmates from the same prison escape by chopper.

He was eventually caught, but old habits die hard. In 2007, he escaped for a third time using a helicopter hijacked by four men.

Payet and his accomplices fled, and the pilot was not harmed. Eventually, Payet was recaptured in Spain.

The prisoner who got a custom-made tunnel

Mexico’s most notorious drug lord has made dramatic escapes from prison not once, but twice.

Joaquin "El Chapo" Guzman
Joaquin "El Chapo" Guzman

In 2001, Joaquin “El Chapo” Guzman escaped from a high-security prison in a laundry cart. It took authorities 13 years to catch him. And when they did, he didn’t stay long.

After only 17 months back in prison, Guzman – whose nickname means “Shorty” – stepped into a shower at a maximum-security prison, crawled through a hole and vanished through a mile-long tunnel apparently built just for him.

The tunnel through which the leader of the Sinaloa Cartel made his escape was not just some hole in the ground. It was complete with lighting, ventilation and even a modified motorcycle on tracks “that was likely used to remove dirt during the excavation and transport the tools for the dig,” Mexican National Security Commissioner Monte Alejandro Rubido said.

The tunnel began with a 20 x 20-inch (50 x 50-centimeter) opening inside the shower of Guzman’s cell, Rubido said.

That opening connected to a vertical passageway going more than 33 feet (10 meters) underground. The passageway, outfitted with a ladder, led to a tunnel that was about 5.6 feet (1.7 meters) tall and more than 28 inches (70 centimeters) wide.

The tunnel stretched for more than a mile and ended inside a half-built house. After a lengthy interview with American actor Sean Penn and text messages with Mexican actress Kate del Castillo, Guzman was captured.

The escape using hacksaw blades in hamburger meat

In 2015, convicted killers David Sweat and Richard Matt did what no one else had done in the 170-year history of New York state’s largest prison: escape from its maximum security walls.

To do so, they cut through a steel wall, carved into a large pipe and worked their way through a maze of tunnels before finally popping out of a manhole in Dannemora, New York.

How did they get the tools to break free? Joyce Mitchell, a prison tailor, has admitted to smuggling hacksaw blades by hiding them in frozen hamburger meat, a law enforcement official said.

But their luck quickly ran out. First, the driver who was expected to pick them up from the manhole cover never showed up. And after more than a week on the run, both were shot by law enforcement officers. Matt died, and Sweat was wounded and captured.

Richard Matt, left, was shot and killed by police. David Sweat was shot and captured.
Richard Matt, left, was shot and killed by police. David Sweat was shot and captured.

The man who wiggled out of a food slot

Choi Gab-bok had a lot of time to kill during his 23 years behind bars. So the convicted robber got really good at yoga – a skill that helped him slip away from a police station jail in Daegu, South Korea.

One night in 2012, Choi waited for officers to fall asleep before squeezing out of his cell door’s rectangular food slot, the Korean Yonhap News Agency said.

To put things in perspective, Choi was about 5 feet, 5 inches tall and weighed 115 pounds. The food tray slot was about 18 inches wide and 6 inches tall.

Choi rubbed an ointment on his skin to help glide between the bars. It worked, and he wiggled his way to freedom.

But six days later, Choi was caught – and put in a cell with a much smaller food slot.