The World of Crazy Prop Bets

Do you like to bet on anything and everything? From typical sports betting to silly or even dangerous challenges, check out these stories of some of the most interesting prop bets in history.

Short for “proposition bet,” a prop bet is a type of wager on whether a specific event will happen or not. Typical sports bets involve betting on which team or player will win a match or whether a team will cover a point spread. These are the types of bets you can easily find at online sportsbooks or from your local bookmaker.

Prop bets, on the other hand, are much more loose and can get downright wacky. Have you ever bet on something in the heat of the moment with friends? If you’ve ever bet on who’ll win this game of mini golf, that would be a prop bet.

Some prop bets can happen between friends with no formally established odds, while others can have full moneyline odds from various bookmakers. Prop bets have a very colored history, and their popularity has continued to grow due to how many possibilities out there exist for random bets.

Some of the Wildest Prop Bets in History

The daring prop bets that people remember the most are big, grandiose spectacles. The bulk of these bets come from poker players, who will apparently find an excuse to bet on anything.

Anything Involving Amarillo Slim

“Amarillo Slim” Preston was a professional gambler known for both his poker skills and his out-of-this-world prop bets, often involving fellow celebrities. He apparently won $300,000 playing dominoes with Willie Nelson and took $2 million from Larry Flynt in a poker game.

One story says that he challenged Wimbledon champ Bobby Riggs to some high-stakes table tennis, with the stipulation that Preston could choose the paddles. He soundly beat Riggs when he brought two cooking skillets as the paddles (and, of course, he’d been secretly practicing his game with a cooking skillet for months beforehand).

In that same vein, Preston once challenged Evel Knievel to a round of golf, but he stipulated that both players couldn’t use standard golf clubs — they had to use hammers. Of course, Preston won.

But probably the wildest prop bet Preston made involved going up against Seabiscuit, the famed racehorse. He bet that he could outsprint the horse over 100 yards. He chose a 50-yard racecourse, which meant that Seabiscuit and his jockey would have to navigate turning around at the end of 50 yards to finish the final 50. By the time the jockey had turned the horse around, Preston was too far ahead on foot to beat.

The lesson here is that, if you want to make your own bold prop bet, you need to have some sort of edge established first.

Bill Perkins Testing Friends’ Physical Limits

Perkins is a hedge fund manager and poker player who loves to set up screwball prop bets with his fellow poker stars.

American pro poker player Jeff Gross is very open about suffering from vertigo. In 2013, however, he accepted a prop bet from Perkins that he wouldn’t bungee off of the 1,149-foot Stratosphere Tower in Las Vegas. Gross pushed through his fear and made the jump, earning six figures for his bravery.

In 2016, Perkins bet Antonio Esfandiari $50,000 that, for 48 hours, he had to get around by lunging instead of walking. By the time Esfandiari had made it to the main event at the PokerStars Caribbean Adventure, he was in such pain that he couldn’t walk. He desperately needed to urinate but couldn’t make it to a bathroom, so he relieved himself into a bottle under the table instead. PCA organizers disqualified him from the tournament for the breach of etiquette.

Brian Zembic Getting Breast Implants

A magician and high-stakes gambler, Zembic was also famous for his ludicrous prop bets, like sleeping a whole night in Central Park with $20,000 in his pockets. However, his most famous prop bet happened in 1996 when he accepted to get C-cup breast implants for $100,000. (He’d even won the cost of the operation, a cool $4,500, in a game of backgammon.)

He kept the implants for two decades, receiving an extra $10,000 for every year that he kept them. In 2016, he appeared on the show Botched and said that he’d finally chosen to get them removed.

Common Outlandish Prop Bets

Beyond these wild one-offs, some prop bets have become so ubiquitous that they’re now popular annual offerings across major sportsbooks.

How Long the National Anthem Will Be

The Super Bowl probably draws the most bets for any sporting event beyond just who will win or what the point spread might be. Prop bets on the Super Bowl can include which team will win the coin toss, how many touchdowns will happen, or which player will score the first points in the game.

But one of the more common and crazy bets you can make is on the length of the national anthem. Every performer puts a different spin on the song, sometimes slowing down the tempo or adding a lot of melisma (stretching a single syllable over a run of notes).

In February 2020, the online sportsbook SportsLine set the over/under line at two minutes, with the negative odds at -220 and the positive odds at +180. Singer Demi Lovato performed the national anthem in 1:50, giving the under bettors the win.

The Winning Team’s Gatorade Color

Another common Super Bowl prop bet involves a tradition that goes back to the 1980s. In 1987, the Giants beat the Broncos in Super Bowl XXI, and the players dumped a bucket of Gatorade on head coach Bill Parcells (as had been their team tradition all season). It’s now become a standard post-game celebration, and bettors have taken to betting on the Gatorade color they’ll see pouring out of a cooler.

In 2019, FanDuel posted these odds for the winning team’s Gatorade colors:

Clear: +200

Yellow: +350

Orange: +350

Blue: +400

Red: + 500

Whether It’ll Snow on Christmas in the U.K.

Every year, the London-based bookmaker William Hill offers odds for whether or not it’ll snow on Christmas Day in Edinburgh, Dublin, and London.

The U.S. Presidential Election

It’s honestly not much of a surprise that people would bet on U.S. elections since they’re already such spectacles. The odds can shift the closer it gets to Election Day, but it’s common to find U.K.-based sportsbooks setting up this prop bet between the two major candidates.

Some Other Prop Bet Ideas To Try

If you’re a football fan, you can try these prop bets on just the Super Bowl:

• Which company airs the first commercial after the coin toss
• Which coach will get mentioned first after the kickoff
• If a former football player is a Super Bowl commentator or analyst, whether he’ll mention his own past Super Bowl experiences
• Whether any player will finish with exactly 69 yards
• Who the MVP will thank first

Instead, maybe you’re a soccer fan. Some prop bets you could make include:

• Which player will score the first goal
• Which player will score the most goals
• First team to score
• Odd or even goals
• How many cards are issued in the game

Meanwhile, if you like betting on U.S. politics, you can try these during any annual State of the Union address:

• The color of the president’s tie
• The length of the speech itself
• Number of times the president says the word “economy”
• Total viewers, according to Nielsen
• How many standing ovations the president gets
• Who the “designated survivor” will be during the event

Prop Bets Can Make Things Even More Interesting

Whether you choose to go the formal route and make a prop bet through an online sportsbook or you come up with something on the fly with your friends, prop bets can add an additional thrill to the larger sports bets you’ve already locked in. They’re typically not the bread and butter for successful gamblers, but you can still win some extra money (and bragging rights) if you make the right call.