6 Stupid Wagers That People Won As Insanely As Possible

We live in a world where gambles have been reduced to drunken frat-boy shenanigans that usually objective 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 kind 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 …

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

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 assert 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, evaluate by this painting .

With a blood alcohol level somewhere around “Oktoberfest, ” the pilot got into his vehicle and drove out to an airfield in New Jersey. If you think that it was irresponsible of him to be driving in his nation, 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 simply in time for last orders.

The police didn’t exactly buy his story that he “suffered* hic* engine* hic* difficulty, ” but they did note that it was a “100, 000 to 1” shot that he didn’t reached any of the buildings on his style down. In the end, the policemen fined Fitzpatrick merely $100 after the plane’s proprietor 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. Abruptly, it was on like Donkey Kong … 2.

“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 matters of great pilots with drinking problems …

# 5. Colonel Duckworth Flew Into An Actual Hurricane For A Drink

There are two types of people in the world. The first kind ensure a gigantic, God’s-fart-level hurricane like this …

… and immediately starts running from it. The second kind jumps into a plane and runs 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.

Mr. Rogers’ seems, 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 largely 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 superstars giggled insuring Duckworth’s aircrafts( AT-6 Texans) being taken away for safety reasons, to which their teachers said that his planes were badass enough to survive flying straight-out through Mother Nature’s continent-leveling hissy fit. The Englishmen took that gamble, wagering a highball as the prize.

“That second airliner? 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 transgressed 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 hour, thus winning him the Brits’ respect and a well-deserved highball.

# 4. Prankster Bet He Can Stage An Old-Timey Flash Mob

Theodore Hook was a famous early-1 9th century prankster who, today, would probably be famous for leaving unattended pouches filled with ticking alarm clock in the middle of a busy New York street. But, more than 200 years ago, he interrupted 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 construct the unspectacular house they just passed( owned by a Mrs. Tottenham) the most famous building in all of London.

“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, necessitating 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 route to just crank these messages out. More than hundreds of thousands of 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 dame 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.

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

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

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

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

In fact, at the beginning of the 20 th 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 gamble 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.

At least he already had a neck bracing .

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 style, they also picked up a mascot — a bulldog who wore steam-punk driving goggles and was named “Bud.”


Things were tough, though. It wasn’t like there were gas stations around back then, and even get 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 dirt fairly often, and, one time, even needed actual cowpokes to lasso the car out of a inundate. Add to that a number of vexing distractions, like one girl sending them 108 miles in the wrong direction so that their own families 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 traversing the finish line.

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 wins here were the people who got to see a kickass puppy wearing goggles.

# 2. A Crazy General Captured A City To Win A B-1 7 Flying Fortress

Bernard “Monty” Montgomery was a British general whose recommending to increase the Allied forces during D-Day may have led directly to victory over Germany . Oh, and almost every Allied commander detesting the man’s guts.

Except for Churchill, but that was more “asshole game acknowledging asshole game.”

Montgomery just had that style of pissing people off through his bizarre and seemingly arrogant behaviour — he once invited the U.S. Army field commander for Christmas lunch, but only gave him an apple to feed. But, the thing that really soured things between him and General Eisenhower arose from a wager Monty had built with Eisenhower’s chief of staff. The story runs 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-1 7 Flying Fortress( a gigantic long-range bomber .)

To Smith, the whole thing was clearly meant to be a gag, but Montgomery took it seriously, and, by “it, ” we entail 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.

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

This behavior pissed Eisenhower something fierce, but, in order to not cause an international incident, he actually dedicated Monty his B-1 7. Montgomery then presumably ran after the poor soldier who built the mistake of betting him “a million dollars” that he’ll never get his plane.

# 1. Annie Kopchovsky Cycled Across The Whole Damn Planet For Feminism

In 1894, two wealthy humen made a drunken gamble over whether or not a woman would be able to circumnavigate the globe on a bicycle. The words: 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.

That’s just how she rolled .

On the day the race began, Annie seemed before a mob of suffragettes and gave a mic-dropping speech, before accepting her first pay 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, firms 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 motorcycle, 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 truly fit in ), before catching another ship to Sri Lanka and … you know what, it would be easier to just show you.

They hooked her motorcycle up to the barge engines to cut down on coal coats .

By the time Annie arrived back in Boston, “shes been” robbed at gunpoint in France and briefly imprisoned in China. And for all her endeavour, “shes been” pretty much forgotten by history, because history can be a real dick to the persons who don’t have one.

Read more: www.cracked.com

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