Beating the Odd – 20 Infamous Bets That Made History

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.

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.

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.