A British engineer named Steve Whiteley won £1.5 million from a £2 bet. He correctly picked 6 winners in a running jackpot and bet on a horse that had lost 28 races.
2. Sir Richard Branson once lost a bet with Air Asia CEO Tony Fernandes on the winner of the 2010 F1 Grand Prix in Abu Dhabi. The loser had to work as a female flight attendant on the winner's airline.
3. In 1986, an Aeroflot pilot named Alexander Kliuyev, bet with his co-pilot that he could land the plane flying blind, he curtained all the cockpit windows and crashed the plane, killing 70 out of the 94 passengers, the pilot survived.
4. A man named Leland Stanford made a bet that all of the horse’s hooves leave the ground when it gallops. He placed the bet at $25,000 and won with the help of photographer Eadweard Muybridge. Muybridge later was the first to make a moving picture.
5. After hearing Kennedy's “end of the decade” speech, an Englishman (David Threlfall) made a wager with a bookmaker of 10 pounds at 1000/1 “that a man will set foot on the surface of the moon before the first of January 1970.” He thought it was “a common-sense bet.”
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Dr. Seuss wrote “Green Eggs and Ham” to win a bet against his publisher who thought that Seuss could not complete a book using only 50 words.
7. Mathematician Paul Erdős, who was an avid amphetamine user, once accepted a friend's $500 bet to stay clean for 30 days. Erdős won the bet but complained that “mathematics has been set back by a month.
8. When a young girl was invited to meet President Calvin Coolidge, someone made a bet against her claiming that it was impossible for the president to say more than two words to her. When the girl told the president about the bet, President Coolidge responded, “You lose.”
9. Dr. Donald Unger cracked the knuckles of his left hand (but not his right hand) every day for more than 60 years to prove that it does not give you arthritis. Neither hand got arthritis and he won the bet with his mother.
10. Steven Spielberg makes money from Star Wars, even today, after a bet with George Lucas that Star Wars would be a flop.
Stephen Hawking had to purchase a one-year subscription to Penthouse for Kip Thorne after losing a bet pertaining to the existence of black holes.
12. Lacrosse was an incredibly violent game created by North American Natives. People were crippled or killed as it was used in place of warfare and diplomatic disputes, where players could even bet their families for slavery to the other team.
13. A guy named Brian Zembic in 1996 had breasts implanted just to win a $100,000 bet. He never got them removed.
14. The first successful US trans-continental automobile trip in 1903 was done on a $50 wager by a man named Horatio Nelson Jackson who did not own a car, had practically no experience driving, and had no maps to follow. It took 63 days.
15. 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.
17. Physicists bet on the Trinity nuclear tests; estimates ranged from a dud to the complete annihilation of the planet.
18. 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.
19. 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.
20. 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.
22. 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.
23. 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.
24. 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.
25. In 2011, Grañén, a tiny Spanish town on the brink of financial ruin bet on the world's biggest lottery and won €700 million.