5 Criminals Who Were Hilariously Good at Escaping Jail

You're never sure if you should admire their brazen creativity, or just make sure you never live too close to a prison.
5 Criminals Who Were Hilariously Good at Escaping Jail

If you want to simultaneously feel abject terror and pride in your fellow man, go research prison escapes. It's a subject that we find fascinating, mainly because we can't tell if these criminals are inspiring geniuses, or if the average prison has the security of a Motel 6. You're never sure if you should admire their brazen creativity, or just make sure you never live too close to a prison.

And the guys on this list? They pretty much proved they could get out whenever they felt like it.

Charles Sobhraj Proves Himself Unjailable (Almost)

5 Criminals Who Were Hilariously Good at Escaping Jail
GQ India

Charles Sobhraj was known by many names, including "The Bikini Killer," "The Splitting Killer," and the one we'll be focusing on (because it alludes to his ability to slip right out of The Man's grasp), "The Serpent."

A career criminal, Sobhraj made his living traveling from the beaches of Thailand to the "hippy trail" in Nepal, conning cash from tourists, and then strangling, drowning, or setting them on fire, and sometimes all three (Sobhraj is a horrible person, in case we neglected to mention that). Most of his early hijinks were of the petty variety, however -- like in 1970, when he was locked up in relation to a jewelry heist in Bombay. That also marked the first in a string of escapes, when he managed to get himself to a hospital by complaining about abdominal pain, then drugged a guard, and scampered out a window with a nice new (and totally unnecessary) appendectomy scar to show for his efforts.

5 Criminals Who Were Hilariously Good at Escaping Jail
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The escape is over so quickly, but the scar is something you'll always have.

He fled to Kabul, Afghanistan, where he was arrested again for failure to pay a hotel bill. This time he cranked the gross-o-meter knob up to 11, using a smuggled syringe to draw his own blood and drink it like some sort of self-loathing Dracula. Taken to the hospital again (where confused doctors probably tried to remove his appendix), he once again drugged a guard and slithered away.

His crime spree roadshow took him all over the Eastern hemisphere from Iran to Greece, where he was again locked up after a robbery. This time he started a fire in the back of a police van and bum-rushed the door when the guards stopped to investigate. This pattern continued until Sobhraj's success at evading confinement began to go to his head -- he started to think of himself as a "Nietzschean character, a criminal Superman."

5 Criminals Who Were Hilariously Good at Escaping Jail
GQ India

A "Jean-Claude Van Damn," if you will.

But when the ponytailed bodies began to pile up, international law enforcement stepped in. When Sobhraj was arrested in New Delhi after posing as a tour guide and poisoning a group of French students with "dysentery pills" that gave them violent diarrhea in the lobby of a busy hotel (he was presumably just being a straight-up dick that time), authorities were able to link him to unsolved murders across several countries. Sobhraj was sentenced to 11 years for one murder plus the French pants-shitters, and it looked like The Serpent's jig was up.

Not the type of guy to let that get him down, he used his skill at manipulating others to ensure that he was treated like royalty while in the slammer. He sold interviews to sympathetic Western journalists and bided his time. It was a calculated move -- by serving the sentence in India, he would avoid a longer sentence in Thailand. When it looked like he might get released too soon, he escaped and got recaptured on purpose, just to allow the Thai statute of limitations to expire.

5 Criminals Who Were Hilariously Good at Escaping Jail
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"Is there any way we could time it so the expiration lines up with my birthday?"

After his release he moved to Paris, where all those interviews he did in prison resulted in him becoming a minor celebrity. Then, apparently tired of basking in the glow of his notoriety, he inexplicably (or absolutely explicably, considering his planet-sized hubris) took a trip to Kathmandu to gamble openly at a casino. Unfortunately (for him, not for society at large), he apparently forgot all about the 30-year-old Nepalese murder warrant that was still outstanding.

See, kids? Your past always catches up with you. Eventually.

Moondyne Joe Is Forced to Break Rocks, Escapes Via Big-Ass Pile of Broken Rocks

5 Criminals Who Were Hilariously Good at Escaping Jail
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The son of a Welsh blacksmith, Joseph Bolitho Johns was better known as Moondyne Joe because he's credited with discovering Moondyne Cave, and also because what the hell else would you call a guy who looked like this?

5 Criminals Who Were Hilariously Good at Escaping Jail
Alfred Chopin

Crazy-Beard Hatchet Joe just doesn't have quite the same ring.

That photo probably tells you every single thing you need to know about Moondyne Joe, but we're going to tell you the rest anyway. In 1848, Joe and a friend were stopped by the police in the wee hours one morning, their arms cartoonishly overflowing with "three loaves of bread, two pieces of bacon, a shoulder of mutton and some suet." This being the mid-19th century, messing with another man's bacon was a serious goddamn offense -- Joe was arrested for theft and promptly deported to the prison colony in Australia.

Once there Joe was issued a ticket of leave, entitling him to all the wonderful freedoms Australia had to offer (i.e., getting horribly mauled by the fauna). He was a good little deported convict until 1861, when he was caught stealing a horse and subsequently locked up. He quickly broke free and re-stole the very same horse plus the magistrate's saddle, because that's just the way Moondyne Joe fucking rolled. He was recaptured two days later and sentenced to three years of servitude.

5 Criminals Who Were Hilariously Good at Escaping Jail
Ivan Tykhyi/Hemera/Getty Images

"Of course you can take stable cleaning du-- Hey, wait a minute!"

After his release he stayed out of trouble for almost a year, after which he was charged with killing an ox with felonious intent because seriously, fuck oxen. He escaped three times in the following four months. The final time he was recaptured after stealing 36 ladies handkerchiefs, because Moondyne Joe's story wasn't quite absurd enough yet.

That's when Joe was chained by the neck to a post while the governor constructed an escape-proof cell, sarcastically telling Joe, "If you get out again I'll forgive you." While neck-chained in the prison yard, Joe was tasked with breaking rocks. The guards were tasked with removing said broken rocks at the end of each day, but as the guards got lazier, Joe's big-ass rock pile got bigger. So big, in fact, that it neatly disguised the big-ass hole he knocked through the prison wall and used to let himself out by way of the superintendent's backyard.

5 Criminals Who Were Hilariously Good at Escaping Jail
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"We would have checked, but he put up a 'No Guards Allowed' sign. What were we supposed to do?"

Joe popped up again two years later while robbing a winery, but he convinced the governor to honor his promise and let him go. Towards the end of his days, Joe went from a little crazy to bat-shit crazy, and he ended up in lunatic asylums from which, in true Moondyne Joe fashion, he escaped four times before his death in 1900. Today he's best remembered during the annual Moondyne Festival, which, in addition to a Moondyne Joe cosplayer running around causing all manner of ruckus, features mustache and cleavage competitions.

We have a feeling Moondyne Joe would've wanted it that way.

Paddy Mitchell Nearly Explodes His Own Heart

5 Criminals Who Were Hilariously Good at Escaping Jail
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With a name like Paddy Mitchell, it's pretty much a given that this guy was going to become a famous outlaw. Like Jesse James, Al Capone, or Machine Gun Kelly, it's a name that his parents should have taken one look at and said, "Nope, that's an outlaw name. George it is." But they didn't, and during his criminal career Mitchell robbed a number of banks that (depending on whom you ask) ranges from 100 to "Shit. All of them? Probably all of them."

5 Criminals Who Were Hilariously Good at Escaping Jail
Photodisc/Photodisc/Getty Images

"All. Of. Them."

Mitchell's gang was revolutionary, in so far as bank robbing can be revolutionary. Dubbed the Stopwatch Gang for the Flavor Flav-style stopwatch one of its members wore (the gang's claim to fame was being able to rob a bank in under two minutes), they also wore presidential masks while carrying out their robberies -- and if all this sounds overly familiar, yes, they were the inspiration for Patrick Swayze's bank-robbing, surfer gang in Point Break.

After more than a decade of success during the '70s and '80s, Mitchell got himself caught -- but he, of course, was not content with his involuntary vacation, even with all expenses paid by The Man. His first escape in 1986 was a simple affair: He and his gang removed some ceiling tiles, crawled through an A/C duct, and waltzed right out of the prison. They were soon recaptured, and the message Mitchell took from this was that his escape attempt simply hadn't been ballsy enough.

5 Criminals Who Were Hilariously Good at Escaping Jail
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"Where's your showmanship? Presentation counts, you know."

Now, you probably know from decades' worth of depictions of prison life in the media that cigarettes are as good as gold on the inside, but you probably don't know about something else they're good for -- namely, faking a heart attack, which you can do by simply soaking a cigarette butt in water overnight and then drinking the resulting liquid nicotine goodness (don't try that at home, kids). Mitchell, obviously a big fan of the "more is more" approach, soaked an entire pack of cigs in water, ran three miles around the prison exercise yard, and then drank that refreshing cancer sludge.

His ticker damn nigh exploded. His heart attack symptoms were so real -- because, basically, they were -- that guards rushed him to the local hospital ... where his two partners were posing as emergency room workers. Mitchell made a quick getaway to the Philippines, only returning to the U.S. to pull an occasional bank heist until he was finally caught for good ... 15 years later. Not content to check out until he ticked off the last box on his "don't be like Paddy Mitchell, kids" checklist, in 2007 he died in prison at age 64 of lung cancer.


Hopefully he died as he lived; with a killer beard.

5 Criminals Who Were Hilariously Good at Escaping Jail

Chris Gay Steals a Country Singer's Tour Bus, Has a Country Song Written About Him

5 Criminals Who Were Hilariously Good at Escaping Jail
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Chris Gay's escapes may well lack the finesse of some of the other escapees on this list. He's faked suicide attempts, he's picked handcuff locks using paper clips, zipper tabs, and broken ballpoint pens, and he's camped out in air ducts for days at a time -- that sort of thing. But what he lacks in sophistication, Gay makes up for in sheer numbers: with an unfathomable 13 escapes over the course of his career, he's possibly the most successful prison escapee ever, and has most certainly earned every bit of his nickname, "Little Houdini."


"Only amateurs rely on dislocating their shoulder."

In his most well-known dash for freedom, Gay escaped a South Carolina prison transport, outran 19 police officers and two K9 units (he sprinkled pepper all over his clothes to throw off the scent), hightailed it through Georgia in a stolen Freightliner, then jacked a Wal-Mart tractor-trailer in Tennessee.

So why all the hubbub? Was he putting as much distance as humanly possible between himself and an overly affectionate cellmate? Late for an offer for Get Out of Jail Free cards to the first 50 inmates? Missing the series finale of Breaking Bad? Nope. As it turns out, Gay was simply reenacting Cool Hand Luke: he was running toward his mother, Annie, who lay in her death bed, clutching a photo of her boy as she succumbed to cancer.

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He hacked off a few parking meter heads and only ate hard-boiled eggs just to complete the image.

Excuse us for a second -- tiny, invisible bugs just flew straight into our eyeballs.

Anyway, Gay made it within 50 yards of his mother's front door before his commandeered transport got stuck in the mud. The cops and their dogs caught up with him then, but (much like his namesake) Little Houdini hastily vanished. He got busted two days later at a NASCAR track in Florida, where he was found driving the stolen, million-dollar, chip bag-littered tour bus of country star Crystal Gale.

5 Criminals Who Were Hilariously Good at Escaping Jail
Gayle Enterprises via Orland Sentinel

"I don't know the meaning of the word 'inconspicuous!'"

His efforts to see his dying Ma (perhaps deservingly) inspired a bluegrass song, and (perhaps undeservingly) inspired a whatever the hell this is:

Michel Vaujour Escapes by Way of a Helicopter and Nectarine Grenades

5 Criminals Who Were Hilariously Good at Escaping Jail
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Ask Frenchman Michel Vaujour to define "prison," and he'd likely say, "a place to escape from." Then he'd make it all creepy by going on to describe pulling off a successful prison escape as "almost orgasmic."

By the time most kids finally figure out what they really want to do with their lives after wasting six full semesters' worth of their parents' life savings, Vaujour (who majored in armed robbery, with a minor in grand theft auto) was getting recaptured from his second prison escape. That's when he snuck a piece of cheese from the prison commissary and carried it with him for months, waiting for an opportunity to nonchalantly bump into a prison guard (something that's easier said than done when one smells like months-old cheese) so he could snatch his keys and copy them using his cheese-mold.

5 Criminals Who Were Hilariously Good at Escaping Jail
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His initial strategy of asking the guards to saw his cheese for him with their key was unsuccessful.

Vaujour only made it a month on the outside after the Great Cheese Key Escape. After his recapture, he decided to rip a page from John Dillinger's notebook and created a model gun using soap, a piece of a battery, and some nail clippers. He then one-upped ol' J.D. by using his fantastically fake pistol to hold a magistrate and a few officers hostage before escaping again.

His next arrest came in 1981, and this time the police weren't fucking around: to reduce the risk of a fifth escape, Vaujour was transferred at least once every three months. So he did what any rational human being would do: he convinced his wife Nadine to take flying lessons and bust him out of prison in a friggin' helicopter. In 1986, after using the threat of nectarines painted to look like grenades to force his way to the roof, Vaujour copped his best action movie pose on the ladder thrown down from his wife's copter, presumably flying an unwavering bird at every last slack-jawed prison guard as he ever-so-slowly floated away.

5 Criminals Who Were Hilariously Good at Escaping Jail
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"We're not even going to search for him. Motherfucker earned that shit."

Five months later, Vaujour was caught robbing a bank and fatally shot in the head.

Wait, no -- apparently this guy is pretty goddamned good at escaping certain death, too. He recovered from the headshot and -- after a failed attempt at another freaking helicopter rescue by his second wife, Jamila -- apparently decided to go straight and serve out his time. He was released in 2003 after spending 17 years in solitary confinement. The hardest part, according to Vaujour? "Not to escape."

5 Criminals Who Were Hilariously Good at Escaping Jail
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Plus helicopter parking is crazy expensive.

We assume resisting the urge to whip up some more fruit grenades just for the hell of it came in a close second.

E. Reid Ross is a columnist at Man Cave Daily. You can also follow him on Twitter. Charlie Fox is an aspiring screenwriter currently based in Detroit, and is always looking for additions to his writers group. Interested? Contact him at cpatton.lhup@gmail.com.

For more prison stories that need the Hollywood treatment, check out The 5 Most Amazing Things Accomplished While in Prison and 6 Insane Prison Escapes That Actually Happened.

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