From power tools to helicopters: 6 famous prison escapes

Story highlights

  • A Frenchman escaped from prison on a helicopter three times
  • A Korean man writhed out of his cell through a food tray slot
  • A Mexican drug lord escaped through a tunnel nearly a mile long

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

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

The French lovebirds

    Nadine Vaujour was so determined to get her husband out of a Parisian prison that 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, and Michel survived being shot in the head during a failed bank robbery.

    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.
    The Frenchman first used a helicopter to flee from a Luynes prison in 2001.
    Two years later, while still a fugitive, he helped inmates from the same prison escape by chopper.
    He was eventually caught, but then he escaped for the third time from another prison in 2007 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 Mexican drug lord

    Mexico's most notorious drug lord has made dramatic escapes from prison not once, but twice.
    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 they didn't hold him for all that 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 in January.
    Joaquin "El Chapo" Guzman

    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 the Clinton Correctional Facility, 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, their expected ride 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.

    Wiggling 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 a skin ointment on himself to help glide between the bars more easily. 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.

    The still-missing Alcatraz inmates

    The whole point of Alcatraz Federal Penitentiary was to keep dangerous inmates locked up on an island prison surrounded by frigid, rough water, so they couldn't possibly escape.
    But they could.
    Alcatraz Island in 2011
    In 1962, Frank Morris and brothers John and Clarence Anglin made intricate dummy heads -- complete with real human hair -- to use as decoys for guards making their nighttime checks. They used homemade drills to enlarge vent holes and slipped through.
    "They then climbed down a drainpipe on the northern end of the cellhouse and made their way to the water," the Bureau of Prisons said. "They used prison-issued raincoats to make crude life vests and a pontoon-type raft to assist in their swim."
    Decades later, it's still unclear whether they made it across San Francisco Bay alive. No signs of the men have emerged, but Morris and the Anglins are considered missing and presumed drowned.
    A mug shot of Frank Lee Morris, taken on his arrival at Alcatraz Federal Penitentiary on January 20, 1960.