We gotta admit it: people will do some unbelievably stupid things for money. To be completely honest, some of the things I read while researching for this article left me either holding my hand in front of my face to try and contain my laughter so as to not cause a scene or completely dumbfounded by the immense and pure stupidity. There is something cruelly appealing we feel (or at least I felt) reading about these loony or disastrous bets. So without further ado, let the countdown of the world’s stupidest bets begin!

#5: Stephen Baldwin, 2008

You know you are a washed up has-been when you bet a girl about 30 years younger than you that you will get her initials tattooed on your body just to get work…then get screwed over. This is exactly what the least known of the Baldwin brothers, Stephen Baldwin, did. His acting career was in a bit of a funk, so he bet Miley Cyrus he would tattoo her TV show character’s initials on his shoulder; if he did, Miley would get him a role on her popular show Hannah Montana. Baldwin went out and got the tattoo and took a picture of himself with the new tat and Cyrus by his side. The funny part is that Miley Cyrus never gave him a spot on the show, and 3 years later the show got cancelled. Talk about humiliating!

#4: Harry Bensley, 1907

This one is truly a historic bet. Playboy and businessman Harry Bensley one day got into an argument with legendary mogul J.P Morgan and the Earl of Lonsdale about whether a man could circumnavigate the globe without being recognized. One thing led to another until finally they bet Bensley he couldn’t do the trek while wearing an iron mask and pushing a baby carriage. Bensley spent 6 years attempting the challenge and never completed it because WWI broke out.

#3: Andrei Karpov, 2007

Ladies, never marry an obsessive gambler. You might end up on the table, and not because you were a little tipsy and got up there to dance. Andrei Karpov of Russia was in really deep during a poker game with friend Sergey Brodov. He was all out of money, so, after a quick inventory of what he had left, he actually proposed betting his wife! Brodov good-naturedly accepted. Karpov lost. When his wife found out, in a livid rage, she divorced Karpov and married Brodov. I’m sure many would do the same.

#2: William Bonner, 2012

Here’s an excellent example why you should never make bets when you’re completely wasted. William Bonner of Augusta Georgia bet his friends at a bar that he could set his own head on fire…and he did. They dumped a shot of Bacardi 151 on his head and lit it. Needless to say, he practically melted his face off and ended up in the hospital. I’d rather not write the word I’m thinking to describe this guy.

#1: John ‘Fatboy’ Powell, 2010

And the winner is…John Powell of Illinois! The aspiring rapper was gigging at a party with his crew the Krazy Killaz, and things got really wild. A buddy was taking bets that he couldn’t take a punch in the face from a female at the party for a whopping $5. 22-year-old Tiffany Startz stepped up to the plate, wound up, and threw a solid punch straight to Powell’s face. Everything was fine until Powell collapsed and was taken to the emergency room where he died of a burst artery due to blunt force trauma…for $5. Startz and his “buddy” Jimmy Mounts were arrested and charged, Startz with reckless conduct and battery and Mounts with reckless conduct for starting the bet. Wow! I’m speechless.

So next time you are ever in the mood for a crazy bet, think twice about it. You might end up jobless, wifeless, faceless, or even dead. Bet responsibly!


Simon is an overactive gambler and the Staff Writer here at Silver Oak. He loves casino bonuses, online slots, and using the em dash too often. Currently, he rests his typing hands in Vancouver, Canada.