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.

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.

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.

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.