6 Stupid Bets That People Won As Insanely As Possible

6 Stupid Bets That People Won As Insanely As Possible

We live in a world where bets have been reduced to drunken frat-boy shenanigans that usually end in a stupid YouTube video of someone clutching his balls in pain. But, it wasn't always like this. Back in the day, wagers were an art form dominated by badass, crazy motherfuckers ready to risk their lives in the suicide-est stunts imaginable, all because someone bet them that they couldn't do it. For example ...

Man Steals A Plane And Flies It Back To A Bar (Twice) To Win A Drunken Argument

6 Stupid Bets That People Won As Insanely As Possible
John Gleeson/iStock/Getty Images

In the early hours of September 30, 1956, licensed pilot Thomas Fitzpatrick was drinking heavily in a Manhattan bar when a patron challenged the man's claim that a flight from New Jersey to Manhattan would take 15 minutes. At the risk of being labeled a liar/sane person, Fitzpatrick decided to go out there and prove Random Shit-Talker McGee wrong.


Probably calling him a "fecking arsehole" on his way out, judging by this picture.

With a blood alcohol level somewhere around "Oktoberfest," the pilot got into his car and drove out to an airfield in New Jersey. If you think that it was irresponsible of him to be driving in his state, then you're really not going to like this next bit. After stealing a single-engine airplane, the still-shitfaced Fitzpatrick flew the craft back to the city and landed it outside the bar just in time for last orders.

The police didn't exactly buy his story that he "suffered *hic* engine *hic* trouble," but they did note that it was a "100,000 to 1" shot that he didn't hit any of the buildings on his way down. In the end, the cops fined Fitzpatrick only $100 after the plane's owner decided not to press any charges, and that was that ... for about two years. In 1958, bar patron Assface McGee (no relation) straight-up called Fitzpatrick a liar when he brought up the whole "Yeah, I landed a plane outside" thing. Suddenly, it was on like Donkey Kong ... 2.

John Muravcki/The New York Times

"You fecking arsehole."

Once more, Fitzpatrick drove out to New Jersey, stole another plane, and landed it smack-dab in the middle of Manhattan. However, this time, he was sentenced to six months in jail, presumably in solitary confinement out of fear that some prisoner would bet him that he couldn't break out of there. And while we're on the subject of great pilots with drinking problems ...

Colonel Duckworth Flew Into An Actual Hurricane For A Drink

6 Stupid Bets That People Won As Insanely As Possible
Harvepino/iStock/Getty Images

There are two types of people in the world. The first type sees a gigantic, God's-fart-level hurricane like this ...

6 Stupid Bets That People Won As Insanely As Possible

... and immediately starts running from it. The second type jumps into a plane and goes flying right into the demonic core to punch the hurricane in the dick, all for the promise of whiskey and club soda. Colonel Joe Duckworth belonged to the second group.

6 Stupid Bets That People Won As Insanely As Possible
via daysgoneby.me

Mr. Rogers' looks, Steve Rogers' balls.

In 1943, Duckworth was training together with British flying aces who had little respect for the ex-commercial-pilot-turned-flight-instructor, though they mostly kept it to cracking a few jokes at his expense due to their terminal Britishness.

The day Joe Duckworth decided he had enough was when Texas was hit by a massive hurricane on July 27. The British aces laughed seeing Duckworth's planes (AT-6 Texans) being taken away for safety reasons, to which the instructor said that his planes were badass enough to survive flying straight through Mother Nature's continent-leveling hissy fit. The Englishmen took that bet, wagering a highball as the prize.

1-152 1-151

"That second plane? My testicles have their own pilot's license."

Duckworth grabbed a flight navigator unlucky enough to be closest to him at that moment (Lieutenant Ralph O'Hair) and set off without official permission. Duckworth approached the hurricane at an altitude of 4,000-9,000 feet while turbulence shook the plane like a "stick in a dog's mouth." Finally, he broke through into the storm's calm, 10-mile-long eye and circled that bastard a couple of times.

He then got back, let O'Hair out, and took another passenger (the base's weather officer) on Uncle Joe's Krazy Twister, flying through the goddamn hurricane a second time, thus winning him the Brits' respect and a well-deserved highball.

Prankster Bets He Can Stage An Old-Timey Flash Mob

6 Stupid Bets That People Won As Insanely As Possible
Alfred Concanen

Theodore Hook was a famous early-19th century prankster who, today, would probably be famous for leaving unattended bags filled with ticking alarm clocks in the middle of a busy New York street. But, more than 200 years ago, he disrupted the social order with stunts such as the Berners Street Hoax. While taking a stroll in 1810, Hook suddenly bet his pal Samuel Beazley that he could make the unspectacular house they just passed (owned by a Mrs. Tottenham) the most famous building in all of London.

6 Stupid Bets That People Won As Insanely As Possible
Wiki Commons

"I'll just tell the press that's where I get my hair done."

Hook went to work, spending the next week sending at least a thousand letters to every conceivable tradesman in London, from sheep-dung picklers to professional orphan punchers, requiring their services at the Berners Street location on a particular date. Just to be clear -- this was in an era before there was any easy way to just crank these messages out. More than a thousand fucking letters, penned by hand, just to pull off this completely pointless prank.

When the day finally came, he holed up in a house across the street that he had rented and watched Mrs. Tottenham, an elderly lady who never did anything to anyone, awake to her version of hell. Over the course of the day, tradesmen of every kind started showing up at her address, including: chimney sweeps, upholsterers, linen-makers, jewelers, barbers, wig-makers, opticians, butchers, piano deliverymen, and even a group of undertakers with a full-size coffin in tow.

Alfred Concanen

On the plus side, if the poor woman got a heart attack then and there,
her wake would have been prompt and legendary.

The street was completely blocked all day as more and more people arrived, kicking off something very much like a riot. Meanwhile, Hook sat watching all of this with glee, presumably never pausing to ask what in the hell he was doing with his life.

6 Stupid Bets That People Won As Insanely As Possible

A Doctor Goes On An Epic Road Trip To Win $50

6 Stupid Bets That People Won As Insanely As Possible

Today, driving across America is something that can be done in a few days, requiring nothing more than some gas money, a taste for fast food and Red Bull, and a high tolerance for public restrooms. But, a hundred years ago, it was a months-long adventure that was the equivalent of trying to traverse Africa. No single paved street connected one coast to the other, there were mountains, deserts, and swamps to navigate, and you were doing it via horse -- owning your own car back then was the equivalent of owning your own airplane today.

In fact, at the beginning of the 20th century, most people considered the car a fad that would soon wear off, like regular bathing or living past 50. Horatio Nelson Jackson didn't share that view. And when some guy in a bar bet him $50 that he couldn't drive a car across America in less than 90 days, he took that bet, despite the fact that he was still learning how to drive.

6 Stupid Bets That People Won As Insanely As Possible
Mary Louise Blanchard

At least he already had a neck brace.

To mitigate that problem, he hired the awesomely old-timey-named Sewall Crocker to be his mechanic and co-driver, and then bought a red 20-horsepower Winton touring car. Along the way, they also picked up a mascot -- a bulldog who wore steam-punk driving goggles and was named "Bud."

6 Stupid Bets That People Won As Insanely As Possible
Mary Louise Blanchard


Things were tough, though. It wasn't like there were gas stations around back then, and even getting new tires that fit became a huge problem. The traveling trio also had to deal with the fact that most roads were unpaved, which meant that they got stuck in the mud pretty often, and, one time, even needed actual cowpokes to lasso the car out of a swamp. Add to that a number of annoying distractions, like one woman sending them 108 miles in the wrong direction so that her family could see the car.

But, 4,500 miles, 800 gallons of gas, and 63 days later, they managed to arrive in Vermont where the car cartoonishly fell apart -- right after crossing the finish line.

6 Stupid Bets That People Won As Insanely As Possible
University of Vermont

Wait, that's how the car is supposed to look like?

Horatio won the $50 but he also spent $8,000 on the journey so, ultimately, the only winners here were the people who got to see a kickass dog wearing goggles.

A Crazy General Captured A City To Win A B-17 Flying Fortress

6 Stupid Bets That People Won As Insanely As Possible
ImageOregon/iStock/Getty Images

Bernard "Monty" Montgomery was a British general whose urging to increase the Allied forces during D-Day may have led directly to victory over Germany. Oh, and almost every Allied commander hating the man's guts.

6 Stupid Bets That People Won As Insanely As Possible
Fred Ramage/Hulton Archive/Getty Images

Except for Churchill, but that was more "asshole game recognizing asshole game."

Montgomery just had that way of pissing people off through his bizarre and seemingly arrogant behavior -- he once invited the U.S. Army field commander for Christmas lunch, but only gave him an apple to eat. But, the thing that really soured things between him and General Eisenhower arose from a bet Monty had made with Eisenhower's chief of staff. The story goes that Monty was at a dinner party with General Walter Bedell Smith, who said that if Monty captured the Tunisian city of Sfax by April 15, 1943, the U.S. government would give him a B-17 Flying Fortress (a gigantic long-range bomber.)

To Smith, the whole thing was clearly meant to be a joke, but Montgomery took it seriously, and, by "it," we mean the city of Sfax, which fell on April 10. And once it did, the British general immediately sent a telegram directly to Eisenhower, demanding his flying gun city. This is probably a good time to mention that Montgomery might have had Asperger's.

6 Stupid Bets That People Won As Insanely As Possible
National Archives & Records Administration

That explains why he personally made sure every Nazi at Sfax was shot an even number of times.

This behavior pissed Eisenhower something fierce, but, in order to not cause an international incident, he actually gave Monty his B-17. Montgomery then presumably went after the poor soldier who made the mistake of betting him "a million dollars" that he'll never get his plane.

Annie Kopchovsky Cycled Across The Whole Damn Planet For Feminism

6 Stupid Bets That People Won As Insanely As Possible
ChamilleWhite/iStock/Getty Images

In 1894, two wealthy men made a drunken bet over whether or not a woman would be able to circumnavigate the globe on a bicycle. The terms: She had to do it within 15 months; she had to collect the signatures of American consuls in the various cities she passed through; she had to start with no money; she couldn't accept any charity; and she had to finish the race with $5,000 earned through her own ingenuity. Boy, these were probably the most clear-headed drunks we ever heard of.

Anyway, a 20-something Jewish mother of two called Annie Kopchovsky chose to accept the wager, despite how insane it was.

Towne Portrait Studio

That's just how she rolled.

On the day the race began, Annie appeared before a crowd of suffragettes and gave a mic-dropping speech, before accepting her first payment of $100 dollars from the Londonderry Lithia Spring Water company. They agreed to sponsor her in exchange for Annie changing her name from Kopchovsky to Londonderry because, back then, corporations didn't fuck around. And with that, the woman who only had two bicycle riding lessons, set out on her journey with no one for company other than her thoughts and a pearl-handled revolver.

First, she traveled to Chicago by way of New York, before buying a new, lighter bike, turning around, cycling back to Boston and starting again. She cycled back to New York, then caught a ship to France, before cycling south to Marseille. There, she caught another ship to Egypt, cycled through Jerusalem and then across Saudi Arabia (where her five-layer burlap dress must have helped her really fit in), before catching another ship to Sri Lanka and ... you know what, it would be easier to just show you.

SCENLIND enstu SLSERLA woa CANADA ASA t1nss o LAZ Map of the Worid. Showind Route Traveted y Annle Lendenderry.
via bikingbis.com

They hooked her bike up to the boat engines to cut down on coal coats.

By the time Annie arrived back in Boston, she had been robbed at gunpoint in France and briefly imprisoned in China. And for all her effort, she has been pretty much forgotten by history, because history can be a real dick to those who don't have one.

Then there's the opposite of these folks: People who probably should've quit while they were ahead. Or never started to begin with. Check out 6 People Who Died In Order To Prove A (Stupid) Point and read about the French tailor who laughed at gravity then died. Or check out some world-changing wagers in 5 Stupid Bets That Changed The World, like the guy who bet Dr. Seuss couldn't, well, be Dr Seuss.

Subscribe to our YouTube channel to see the ordeal every character in shit writing faces in How To Survive Life As A Character In A Bad Work Of Fiction, and watch other videos you won't see on the site!

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