In 1956, for a bet, while drunk, American pilot Thomas Fitzpatrick stole a small plane from New Jersey and then landed it perfectly on a narrow Manhattan street in front of the bar he had been drinking at. Then, two years later, he did it again after a man didn't believe he had done it the first time.
In 2000, a medical school student named Michael Burry quit school to start an investment firm with money borrowed from family, bet against subprime mortgages and walked away with $100 million in profit.
13Trinity nuclear test
Physicists bet on the Trinity nuclear tests; estimates ranged from a dud to the complete annihilation of the planet.
A Texas man named Ulysses Baxter once spent 22 days using only his nose to push a peanut all the way up Pikes Peak for a $50 bet.
In 1977, a Las Vegas casino magnate once bet Stu Ungar (future three-time World Series of Poker main event champion) $100,000 that he could not count down a six-deck blackjack shoe and correctly guess the last card. Ungar won the bet.
Le Chevalier d'Eon was a French diplomat who lived alternatively as male or female. There was a betting pool over his real gender (male) that closed only after his autopsy.
Nicole Kidman and Michelle Pfeiffer both bet George Clooney $10,000 that he would have kids by the age of 40. Staying childless they sent him the money which he returned, replying double or nothing by the age of 50.
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Pete Conrad's first words on the Moon were said in order to win a $500 bet proving that astronauts are not given a script of what to say when stepping off the ladder.
A Russian named Sergey Tuganov died after winning a £3,000 bet that he could have sex with two women continuously for 12 hours. He used an entire bottle of Viagra and died from a heart attack.
A man named Ashley Revell sold all his possessions including his clothes, went to Las Vegas and bet the whole lot of $136,000 on a single game of roulette with 50/50 odds, and won.