The Most Outrageous Prop Bets in Sports You’ve Ever Heard About

If you enjoy betting on sports related activities, you’ll understand the fun that can be had when it comes to proposition bets (also known as “prop bets”). Some very funny and outrageous prop bets have made it into the world of sports. A little bit of odd, unconventional fun can go a long way towards bringing happy smiles to people’s faces. And sometimes they even add to the old bank account – or take some away. The nature of the prop bet allows those involved to have fun and not take themselves or the situation seriously, since this type of fun will not change the outcome of the game, which is the really important issue, as we all know.

You don’t have to visit a bookie or go to the big casinos to place your bets – organize this fun activity among your friends and get more fun out of the game as you watch on TV!

Super Bowl

Prop Bets
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Of course the Super Bowl is BIG in America. In the last few years some outrageous, crazy – even weird prop bets have been placed from anything relating to Madonna wearing fishnet stockings to Tom Brady’s son wearing a Tom Brady Jersey during the game. Or Kelly Clarkson’s bare belly showing during the singing of the National Anthem during the 2012 competition. The 2013 bets were equally strange: You could wager on Beyonce being joined by Jay Z during her half time show, or even what the predominant color of her top would be. Strange yes – but also true.

Here are some more crazy prop bets for you: From the 2015 game the following must surely rank right up there with the most outrageous:

These are so-called ‘calamity’ bets: The odds of the power going out in the stadium at 44/1; the goal posts falling down at 33/1 and the odds of a streaker running across the field at 50/1. Or these: Which coach was going to be mentioned first by name after the start of the game, and bets concerning Katy Perry’s dress code at her halftime show – skirt, dress, pants below the knees or shorts above? Or even her hair color: brunette (odds of Katy being brunette at 1/2, red at 10/1 and blonde at 12/1). You decide which are the funniest, craziest, most outrageous bets by which bring the quickest smile to your face.

Prop Bets Aren’t New

The idea of the prop bet is not new or strange. It is interesting to see that it existed even as far back as 1693 in London. What started out as a coffee house called Mrs. White’s Chocolate House (named after the man who started it, an Italian by the name of Francesco Bianco) later simply became known as White’s and became one of England’s most famous all-male clubs; situated at 37-38 St. James Street since 1755, the club may still be the grandest and most exclusive gentleman’s club around. Soon after it started, it also allowed patrons to gamble, and a betting book of some very unusual proposition bets was kept during the 18th and 19th centuries. One such bet concerned a very rich peer, Lord Alvanley, who bet a friend in the early 19th century for £3,000 that one raindrop would beat another to the bottom of the bow window at the front of the club. The betting book does not mention the outcome; however, in today’s money that wager amounts to almost £200,000!

Other well-documented prop bets concern Alvin ‘Titanic’ Thompson (November 30, 1893 – May 19, 1974) who once wagered his gambling companions on a road trip that a sign that read “20 miles to Joplin, Missouri” was in fact wrong (only after he’d hired a man to dig up the sign and move it 5 miles closer to Joplin). He complained about the sign’s inaccuracy, wagered his friends and, of course, won!

And then there are those proposition bets that started as dares or “exile” bets, whereby a wager is taken out against a gambler for doing something quite unfamiliar to his nature. Gamblers like the excitement and surroundings of casino halls and bright lights, as well as their independence and freedom; those are the conditions under which they function best. Also, the casino is where they make their living. So in the early 1990s a fellow gambler entered into a wager with two-time World Series of Poker winner John “Johnny World” Hennigan, the bet being that Hennigan would have to survive 6 weeks in Des Moines, Iowa. Now, for a man who loves the excitement of Las Vegas and Atlantic City, this proved too much and he left after 2 days, thereby losing the wager. To settle the bet, Hennigan accepted that he had lost and actually paid the other guy a settlement to leave Des Moines early.

Also the Professionals

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The idea of the prop bet has been around for a long, long time as we can see. Because betting is at the heart of the casino player’s passion, it is not uncommon for gamblers to also get involved in proposition bets. A good example concerns Phil Hellmuth, professional poker player and winner of multiple World Series of Poker Bracelets (14, in fact) and the 1989 WSOP Main Event Champion. Hellmuth and Huck Seed, himself winner of the WSOP Main Event in 1996, once entered into an unusual prop bet: Seed had to stay in the ocean for 18 hours straight, but he lasted only 3 hours, thereby handing the wager and a handsome amount of cash to Hellmuth.

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A very confident bet came ahead of the 2014 WSOP season from Daniel Negreanu, one of poker’s all time biggest stars with 6 WSOP bracelets to his credit, as well as 2 WPT championship titles. Negreanu invited anyone to bet against either him or Phil Ivey winning a bracelet at one of the WSOP events of that year. His wager was simple: an even-money bet with the message “…One of us wins, you lose.” The minimum bet was $5K. Because betting is such a big part of the life of the gambler, you can be sure they’re keen to come up with a prop bet when it concerns their mates and fellow gamblers.

Tennis and Other Sports

Either online or among friends, tennis prop betting is common and a fun way of creating some excitement. There are quite a number of possibilities: Who will win which set, who will win the match, how many aces in the men’s game – a great number of bets to be considered. Now these may be just ordinary bets, not outrageous like some of those we find in, for instance, the NFL as we’ve seen. You will find that bettors get involved too in prop bets for games in the NBA season. Typical prop bets include first half total, total team points and total assists.

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Even boxing gets its share of funny and outrageous prop betting. In what was billed as one of the greatest contests in recent years, the matchup between Floyd Mayweather and Manny Pacquiao on May 2, 2015 at the MGM Grand Garden Arena in Las Vegas attracted the following: Would Justin Bieber, the Canadian pop star of “Baby” (his 2010 hit song) fame, be wearing a hat during his walkout with Mayweather, or would he be wearing sunglasses? Another one was: Would 50 Cent walk out with the boxer?

Outrageous wins the Day

It seems that as long there are sportsbooks and online prop betting opportunities, the craziest, most outrageous bets will be placed and gamblers and prop betters will have fun. That is after all what prop betting is mainly about. A few good laughs at ourselves, with a bit of craziness in the mix. It is not about who’s winning the game; it is about supporting the oddest prop bet!