The Strangest Bets Ever Made

Side bets can be a fun way to up the ante when playing in a casino. But sometimes, they can get out of hand, especially when there are celebrities playing, leading to the players making bets off the table, which have to do with their personal lives instead of a card flip or dice roll.

We know you’ve probably heard of some strange side bets, but we hope to surprise you with some of the ones we found. Read on to discover some of the craziest side or prop bets ever made!

1. Leaving Las Vegas for Des Moines

Several years ago, John Hennigan bet over $100,000 that he could leave Las Vegas to live in Des Moines for six weeks. While this might not seem all that crazy, Las Vegas and Des Moines are about as different as can be, with one having everything available 24/7 and the other having most options only open from 9 to 5.

Turns out Hennigan bit off more than he could chew because the Poker Hall of Famer only lasted for a whopping two days before he bought out of the bet so he could return to Las Vegas.

2. World Series of Poker Bracelets

In 2016, Vanessa Selbst was blackout drunk at the PokerStars Caribbean Adventure when she bet Jason Mercier 180:1 (at $10,000) that he couldn’t win 3 bracelets that summer at the WSOP.

On the surface, it looked like an easy bet because winning one bracelet is difficult, much less three. However, Mercier ended up winning two bracelets and just narrowly missing taking home a third, meaning Selbst was inches from losing a massive portion of her net worth.

3. National Anthem Length

Now this one is an official prop bet, and you may have heard of it, but we still think it is one of the strangest ones of all time. In NFL football, during the Super Bowl, sports bettors can place their bets on how long the Star Spangled Banner will last.

We aren’t kidding. Typically, this is a simple over/under bet, and we doubt it is very popular because you have to know the singer and how long the flourishes they add to the song will last—but hey, it is still an available (and legal) side bet.

4. McDonald’s Prop Bet

Of course, a McDonald’s prop bet made our list! In 2017, Michael Noori bet he could eat $1,000 worth of McDonald’s food in a 36-hour period. What’s more is that he couldn’t eat more than $200 worth of salads, and drinks didn’t count. For those who have visited McDonald’s, you already know that $1,000 will buy you a lot of food, especially with the salad limit.

He gave those interested 5:1 odds and headed to the golden arches. As predicted, he lost, tapping out after only 10 hours with hundreds of dollars left before victory.

5. Betting to Get Beat Up

Johnny Moss is most famous for his three WSOP wins, but there is also a legend of a particular side bet he participated in.

Supposedly, he requested to fight a well-known boxer with the conditions being that if he won, he would win $15,000, and if he lost, he would have to pay $1,000. The only condition was that Moss got to take the first hit.

As you would expect, even with taking the first hit, Moss lost terribly and ended up in a hospital. We like to think he learned a valuable lesson, though.

6. Things Never Change

In 1989, a man in Wales placed a very unique parlay bet that over the next 11 years, 5 things would remain the same. The first three were that the TV shows “Home and Away,” “Neighbors,” and “EastEnders,” would all still be on air. He also bet that singer Cliff Richards would be knighted, and that the band U2 would still be together. The bookmaker gave him 6,479:1 odds.

Apparently, it was a good bet, though, because the man won, walking away with an astounding 194,400 British pounds in 2000.

7. Free Throws

In April 2020, Mike McDonald bet he could make 90 out of 100 free-throw attempts by the end of the year. He put his money where his mouth was, tying an impressive $250,000 to the bet.

Many individuals were foaming at the mouth to be a part of the bet, considering most NBA players have a free-throw success rate of less than 90%. Not only that, but McDonald had no basketball experience.

To everyone’s surprise, McDonald won. And he did so long before the bet was set to expire in December 2020. By August 2020, he’d completed it and collected his winnings.

8. Everything on Red

In 2004, Ashley Revell sold everything he owned and put it on a single roulette spin. His bet was broadcast on national TV and ended up being a whopping $135,300.

He placed his bet in the Plaza Hotel and Casino in Las Vegas, and lucky enough, he won. He took home $270,600 (to a cardboard box on the street, we assume) and used the money to open his own company. It was apparently a one-time thing, though, because his company closed only a few years later.

9. Fake Boobs?

During our research for this article, by far the strangest prop bet we came across was Brian Zembic. It was well known that Brian Zembic would do anything to win a bet, including living in a friend’s bathroom for a month (and he only won $7,000 for that one!) But the craziest bet he ever made was to get breast implants.

Apparently, the bet was this: he had to get breast implants, and if he kept them for a year, he would receive $100,000. Zembic even took this a step further, finding a plastic surgeon who liked to gamble and wagering on the surgery. When Zembic won, the surgery itself was free, and Zembic had his breast implants.

Zembic did go on to keep them for a year, but in a strange twist, he liked them so much he kept them for over two decades, even turning down a bet to have them removed. In the end, it was Zembic’s daughter who was finally able to convince him to remove the implants.