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.
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.
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.
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.”
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.
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.
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.”
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8Dr. Donald Unger
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.
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.