The World’s Weirdest Bets

Gambling has everything to do with limits, yet some gamblers will go to wild lengths in pursuit of that flutter all players crave. With bookkeepers willing to put a line on just about any outcome you could imagine, the gambling world is primed for some outlandish and strange wagers.

From the strangest bets you can make, to some outrageous gambling behavior, here are some of the wackiest bets that you can place a bet on.

Page contents

Top 5 Weirdest Bets of All Time

Sam, I am

Sometimes it takes a cash wager to push someone to new heights of achievement. In 1960, Bennett Cerf, the founder of publishing giant Random House, made a wager with a noted children’s book author. Cerf bet the author they couldn’t compose an entire story using less than 50 unique words. The author took up the challenge with gusto.

Man - Bennet Cerf

His name? Theodore Geisel, better known as Dr. Seuss. The result of the bet? Green Eggs and Ham, a classic book so ingrained in the culture that American Supreme Court Justice James Muirhead referenced it in an official court opinion.

Rumour has it that Cerf never paid Geisel, but the book sold over 8 million copies. This led to Geisel making a small fortune over a seemingly impossible task.

Betting Against Yourself

A Brit’s slick trick to avoid taxes ended up benefiting everyone involved (besides the Crown). In 2005, 91-year-old Arthur King-Robinson wagered £500 on 6:1 odds he’d be dead by year’s end. He finally found a bookmaker who took the macabre bet, which turned out to be King-Robinson’s attempt to skirt an inheritance tax.

It turns out King-Robinson won by betting against himself. He survived the year, sidestepped the death tax and his bookmaker pocketed the £500.

Betting on Armageddon

Sometimes you have to appreciate the intrepid gambler who will do anything to secure a wager. As the year 2000 loomed, there was mass-hysteria, because of the world-ending apocalypse foretold in a Mayan prophecy. Londoner Matthew Dumbrell angled to cash in, taking a 1,000,000:1 bet that the world would be annihilated in Y2K.

The Name is… Travolta?

Rumours abounded in 2014 that Sony Pictures would tap Idris Elba as the first non-white James Bond. Unfortunately, this step into the 21st century for the film franchise failed to materialize.

Actor - John Travolta
Other prospective 007 candidates included George Clooney at 500:1 odds, same for a Sean Connery return, and a long 1000:1 for Pulp Fiction star John Travolta. It doesn’t roll off the tongue for some reason.

Little Pickle

Three months before the 2016 US presidential election, Donald Trump’s once-long 1000:1 odds of winning the election had shrunk to 7:4 (What are you doing Americans?!) A more contentious battle was being waged over the size of his male appendage.
List of candidates to Americas president

Trump’s manhood has been the subject of media scrutiny for decades. In the summer of 2016, odds stood 50:1 he packs less than four inches and a short 11:4 betting on 7.01-8 inches. Truly a betting line for the ballsy.

Top 5 Wild Wagers You Can Place Today

Celebrity Deaths

Ever had an inkling someone famous wasn’t long for this world? Doug Stanhope’s Celebrity Death Pool lets you place wagers on which celebrities will die before age 50. Sign up with friends to participate in celebrity mock drafts.

Type of bets

Pack your “Funeral Home” to win cash and prizes. The Celebrity Death Pool notes that it’s “forbidden for players to harm, murder, or otherwise affect the health of” celebrities in pursuit of profit.

The Next Pope

Even though Pope Francis of Argentina is still alive, there’s debate among online bettors over who will be next.

List of bets - who will be nest papa after Francis |

Cardinal Luis Antonio Tagle of the Philippines is currently leading at +400. Tagle is just a bit ahead of other people, including Richard Dawkins (+37,000) and Bono (+50,000).

Who Will Play Joe Exotic?

Netflix’s sensational Tiger King is gripping television for millions. At the moment, there are no official plans to make a movie out of the series. If a movie was created, you can bet on which actor would play the larger-than-life Joe Exotic.

Type of bet - Who will play Joe Exotic in the Tiger King movie.

Currently, betting is tight: Billy Bob Thornton, Edward Norton and Kevin Bacon sit at 5.2:1, with David Spade at 7:1.

How is Kim Jong-Un Removed From Power?

Kim Jong-Un has a near-unshakeable grip on power in North Korea. Yet longshot bets never deterred serious gamblers.

Current odds for Kim dying in power are 10:1, 5:1 he is removed in a coup (internal or external, doesn’t matter), and there are long 20:1 odds that he resigns voluntarily.

Cheese Rolling Champion

Yes, it is a sport. Each year on Cooper’s Hill in Gloucester, a 9-lb wheel of cheese is shot down the hill at over 70 miles per hour.

Cheese rolling championship

The goal of participants is to catch the cheese, though no one ever has. The first contestant who makes it down the hill hoists the cheese wheel as their prize.

List with recommended online casinos in Canada for 2024


There you have it: some of the oddest bets and wagers in gambling history. What other wacky gambling stories should people know about? Drop them in the comments below.

Lucas Goldberg
Lucas, a seasoned site editor at CasinoCanada, boasts a decade-long journey in the gambling industry with a focus on providing players with meticulous reviews and insights of online games and casinos.
Site Editor
University of Toronto
Bachelor of Arts in Communications, Digital Media, and Journalism, PlayTech Analytics career, communication with users through high-quality gambling content.
Expert in:
  • iGaming Content
  • Bonus Incentives Theory
  • Trend Analysis
Reviewed by Head of Content:
Dmitry Rogalchuk
Last updated on: 20.02.2024

Related articles

Please turn your device for the best gameplay
By using this website, you agree with our use of cookies to improve its performance and enhance your user experience. More info on our cookies policy page.