The Most Bizarre & Successful Prison Escapes Ever

On Thursday, a Pennsylvania inmate succeeded in walking out of prison, and weirdly enough, that's not even one of the most bizarre prison escapes ever attempted. Robert Crissman was reportedly in for a nonviolent crime, but after escaping he allegedly killed a woman, stole two cars, and terrorized the 12-mile area around the prison. He's back in chains now, but Crissman is one of many escaped prisoners to make headlines this year.

But there's also something fascinating with prison escapes. Maybe it's because there are so many movies about them, or maybe it's because some criminals have set the bar pretty high when it comes to making their mad dashes to freedom. Which makes it so disappointing when you find out that Crissman just walked out of prison. Where's the tunnel? Or the getaway helicopter? How can you escape prison without a decoy?

It's a little unfair to Crissman, I guess, when we measure his escape against the famous escapes of prisoners like Frank Morris and the Anglin brothers. Everyone in American knows the story of the notorious escape from Alcatraz, which includes every prison escape trope known to man — dummies in the bed, climbing through vents, jumping fences, shimmying drainpipes, and swimming through dangerous waters.

But there have been plenty of bizarre (and sometimes hysterical) prison escapes that put Crissman and the Alcatraz boys to shame.

Frank Abagnale

Unfortunately, famous con-artist Frank Abagnale wasn't as cute as Leonardo DiCaprio, who played Abagnale in the movie Catch Me If You Can. But he was about 100 times craftier (sorry, Leo). In 1971, Abagnale was sentenced to prison for numerous forgeries and frauds, but when he was dropped off at the Federal Detention Center in Atlanta, the U.S. Marshall forgot his commitment papers. Abagnale used this as an opportunity, and proceeded to convince the guards that he was actually an undercover prison inspector.

Not only did this provide him with better treatment, but he eventually got guards to agree to let him meet up with a contact outside the prison. Needless to say, he didn't come back. But obviously someone thought Abagnale's career of fraud and subsequent escape was, er, admirable, because after he was recaptured and finished up his sentence, he was employed as an FBI crime advisor.

Ted Bundy

Ted Bundy, one of the most disturbing serial killers ever, was also (unsurprisingly) kind of an out-there guy. Instead of hiring an attorney, Bundy decided to represent himself when he was in court facing charges of murder and kidnapping. When in court, Bundy wasn't restrained so he could argue his case, and during a recess he asked if he could go to the library real fast to check out some law books. He promptly crawled through a window and was gone. He was caught six months later and wasn't allowed to play lawyer anymore.

Bundy then decided to escape a second time in 1977. He reportedly piled books in his bed, sawed a hole in the ceiling, and then booked it to Florida. He was recaptured again after brutally murdering three sorority girls. He was then sentenced to death.

John Dillinger

Gangsters were so much more colorful in the 1930s. Take John Dillinger, for example,who broke out of prison at least twice. He's most remembered for his second attempt, however. He either smuggled in or whittled a fake gun made of wood, and may have used shoe polish to dye it black. He then threatened guards with it, locked them up, and drove away in the sheriff's car. "If I ever seen John Dillinger again, I'll shoot him dead with my own pistol," said Sheriff Lillian Holley. "This is too ridiculous to talk about." Dillinger was shot and killed a few months later during a standoff.

David Sweat and Richard Matt

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When David Sweat and Richard Matt escaped from prison, New York's Gov. Andrew Cuomo called the three-week manhunt for them "a nightmare." The case is still currently being tried, and more bizarre information is coming out daily. Sweat and Matt escaped from the Clinton Correctional Facility on June 6, 2015, after digging a sophisticated tunnel out of the prison. Corrections worker Joyce Mitchell confessed to supplying them with the tools to do so, as well as sexual favors and selfies, and planned to be their getaway driver. Mitchell reportedly planned to hire the two to kill her husband, but later talked herself out of it, and stood them up when the two broke out. The search for the two prisoners was followed by the entire country, as many believed they were trying to make a break for Canada. Local towns were on high alert and some schools closed before Matt was shot dead by police and Sweat was recaptured two days later.

Joaquin "El Chapo" Guzman


The infamous drug lord has actually escaped prison two separate times. The first escape in 2001 seemed to be pulled right out of a movie when Guzman got away in a laundry cart. He was free for 13 years before being recaptured. On July 11 he promptly broke out again in what may be one of the most well-executed prison breaks ever. Associates dug a hole in the prison showers that led to a tunnel with a motorized bike, lighting, and air circulation, which led to a nearby house. Guzman's escape even had an effect on American politics, as a Twitter account associated with him began tweeting threats at Donald Trump. Despite talking a big game, Trump reportedly contacted the FBI to investigate. Guzman has still not been found.

Images: Getty Images (2), Wikimedia Commons (3)