After losing a drunken bet with his bandmates, Sabaton singer Joakim Broden had to walk to the band’s next gig. Broden walked from Falun, Sweden to Trondheim, Norway, over ~700km, staying at fans’ houses and accepting food/beer donations along the way to complete the journey.
In 1903 two men and a dog used 800 gallons of gas and spent/lost $8000 over 63 days to travel from San Francisco to New York in a car with no roof or windshield to win a $50 bet that they never collected. That was the first transcontinental trip across the United States in an automobile.
In 1956, for a bet, while drunk, 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 1929 a Texas man once spent 22 days using only his nose to push a peanut all the way up Pikes Peak (for a $50 bet).
In 1980, a Las Vegas hospital suspended workers for betting on when patients would die.