20 of the Most Daring Prison Escapes of All Time

Breaking out of prison isn't easy. You have to have the right tools, a way to get out of your jail cell, a way to get to the outside world, and a way to stay on the lam. It helps to have friends on the outside, some kind of special skill like woodworking or yoga, a lot of luck - or just have a helicopter. What are the most well-known successful prison escapes? Escaping jail isn't easy, but those on this list did the impossible with some of the top prison escapes ever conceived.

Ever since the very first prisoner was kept in a blocked off cave, criminals have been figuring out ways to get back to the outside world. Whether they've smuggled themselves out, tunneled under walls, taken hostages, or gotten some accomplices to fly them out, all of these prison breakouts took great risks to reclaim their freedom. And while all of these prisoner escapes were successful in the short term, most ultimately failed. Even the most creative escapee, with the best prison escapes, finds themselves the subject of a manhunt, with limited resources and few allies to turn to. So most get caught and sent right back - where they usually try to escape again.

Here are some of the most well-known and famous prison escapes or breakouts in history. From recent prison escapes, to historical prison breakouts, these people had had enough of life behind bars and took matters into their own hands.
Photo: Metaweb / CC-BY

  • Three Inmates Break Out of Orange County Jail

    In January 2016, three inmates of Southern California's Orange County Men's Central Jail used a combination of cutting through walls, crawling through tunnels, climbing, and rappelling to break out of the maximum security prison. The plan was aided by a fight between other inmates, which may or may not have been part of the plot, that delayed the normal head count - meaning the escapees had a 16 hour head start.

    The three men, Jonathan Tieu, 20; Bac Duong, 43, and Hossein Nayeri, 37, were awaiting trial for violent crimes, including murder in the case of Tieu. They also likely had help acquiring tools and possibly being picked up after they escaped. Duong turned himself in a few days after the escape, while Tieu and Nayeri were nabbed after San Francisco police received a tip that their stolen white van was in a Whole Foods parking lot. A prison teacher was also taken into custody on suspicion of providing Nayeri maps and tools to aid in the escape.

  • Mexican Drug Lord Sneaks Out Through the Shower

    In July 2015, the Mexican drug lord Joaquin "El Chapo" Guzman escaped through a 20 inch hole in the shower area of his cell block at the maximum security Altiplano Federal Prison. Guzman, the leader of the vicious Sinaloa drug cartel, escaped through a lighted and ventilated tunnel system that stretched almost a mile, ending up at a half-built house outside the prison.

    This wasn't Guzman's first escape - he escaped from another prison in 2001 by hiding in a laundry cart, and eluded authorities until 2014.

    Authorities immediately began a manhunt and questioned prison employees to determine whether Guzman had any help from the inside with his escape. He was able to elude the dragnet for six months later, until he was finally re-captured in January 2016.

    While Mexican officials were light on details, it was revealed that Mexican marines acted on an anonymous tip that the drug lord was hiding out in a small house in the seaside town of Los Mochis, and moved in. Chapo apparently didn't go down without a fight - at least five people were killed in the gun battle that preceded the cuffs going back on him. Marines also found a small arsenal in the house, including a rocket launcher and multiple 50 caliber sniper rifles.
  • David Sweat and Richard Matt Escape from New York

    Clinton Correctional Facility inmates David Sweat and Richard Matt were the subject of both international headlines and a gigantic manhunt after breaking out in June, 2015. The duo meticulously planned their escape, creating realistic dummies of themselves with fake heads adorned with their own hair. Then they cut holes in the walls behind their beds, using tools provided by sympathetic prison employee Joyce Mitchell . Once in the walls, they cut into a two foot diameter steam pipe and crawled their way to freedom. Mitchell was supposed to pick the pair up at the manhole they climbed out of, but got cold feet and checked herself into a hospital - after which she was arrested.

    The two trekked north, staying in hunting cabins and nearly being caught several times before splitting up and taking different routes. Hundreds of police and federal agents took to the woods of New York state to find the pair, and were eventually successful. Matt was found and shot dead on June 26, and Sweat was captured alive two days later.
  • Ted Bundy Escapes from the Library

    After he was captured in Colorado, vicious serial killer Ted Bundy had one last trick up his sleeve. It involved the maneuver that’s traditionally saved for particularly crazy perps on Law & Order: he represented himself in court. As part of his “education,” Bundy was allowed to visit the prison library by himself. He had already been excused from wearing handcuffs in court, presumably so he could make grand gestures and pound on a table.

    Once he was alone and unfettered, Bundy simply jumped out of the second-story library window and made a run for it. He was captured a week later, and soon escaped again (through a hole he’d sawed in the ceiling of his cell) and made his way to Florida – where he committed three more murders before being captured once again.
  • Richard McNair Mails Himself to Freedom

    Convicted murderer Richard McNair had already escaped from a prison in Louisiana by running out of an interrogation room and crawling through an escape tunnel. But his 2006 breakout was legendary in its simplicity. He had gotten a job in the prison mail room, and took the opportunity to hide in a pile of shrink-wrapped packages.

    Once he was mailed out of the prison, he moved north, quickly being stopped by a police officer. But in an early viral moment, he was filmed by a police dashcam blathering his way out of being arrested – despite giving multiple names during the conversation and matching the description of an escaped fugitive. He was eventually tracked down in Canada, thousands of miles from the prison, and recaptured.
  • The 22 Escapes of Brian Bo Larsen

    Danish career criminal Brian Bo Larsen has escaped from various Denmark prisons an astonishing 22 times, sometimes by digging through or under walls, other times by smuggling himself out with garbage. He most recently busted out in 2014, escaping Vridsloseselille prison outside Copenhagen by sawing the bars off his cell window with a hacksaw. He then used a rope ladder to climb to the top of the roof, then another to climb back down to freedom.

    In this case, freedom didn’t last long, as Larsen was arrested after plowing a stolen car into a ditch while high on drugs.