Craziest Bets

Mark McKenna
May 3, 2010
2 Comments
Hard to see the winner here

Hard to see the winner here

Take a moment to reflect on the craziest bet you ever took, ever made or ever hear of…Now ask yourself, who really won that bet?

People do the most bat shit craziest things over bets. How many of us in our young buck years bet a friend to go grab Chesty Morgan’s breasts and make honk honk noises, or to put gum on the teacher’s seat? How many of us have taken that bet to beer bong 10 beers in 2 minutes? Sometimes people go too far and sometimes they don’t go far enough, but a bet is a bet and only brave or stupid men depending on your opinion, take the craziest bets. Take Jim Harrison for example, a college student who ate 450 hot dogs in a month to win a $1500 bet. Read more.

I hope the years shaved off his life were worth it. Either way he’s a champion by all accounts. That’s a difficult bet to win. Try asking a lady friend how many wieners she can take down in a month and you might get slapped. In light of crazy bets, here are some of the more ridiculous bets that have ever been made. Read more.

Bettors will wager on the most strangest things, it’s a phenomenon that has existed for hundreds of years. Case in point, as taken from the number five craziest bets of all time according to onlinebetting.net: In 1907, London man Harry Bensley bet £21,000 that he could walk around the world without being recognized. The rules were Bensley had to wear a mask the whole trip, pay his way by selling pictures of himself, find a bride during the trip, push a baby stroller and carry only one change of underwear. The story is he was on his way back home in 1914 when he reached Italy and World War I broke out, thus ending the trip.

You know, bettors love to gripe about how they got screwed over by circumstances outside their control; how do you like a World War happening to wreck your bet? Talk about a bad break.

Then of course there are those bets that even when you win, you’ve truly lost. We all probably have a number of funny stories and examples of bets between friends where the bet was so outrageous, there really couldn’t be a winner. I remember back in my school days on a field trip, I bet a buddy of mine $5 while we were on the bus that he could not drink a giant Big Gulp of Dr. Pepper, down a Oreo cookie large blizzard and eat two greasy cheeseburgers in less than five minutes. Amazingly, he won that bet, but every kid on that bus lost that bet, when he began puking profusely all over the bus.

As long as betting exists there will always be those that push the boundaries of sanity. To those brave reckless souls, we salute you for keeping us all entertained and providing benchmark memories of absolute tom foolery.

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  • James

    my craziest bet was wen i bet my house for a computer and i won!!!

  • James

    my craziest bet was wen i bet my house for a computer and i won!!!