The 10 Stupidest Bets Ever Made

Stephen Baldwin, 2008

The least famous of the Baldwin brothers has had a pretty rough time of it the last few years, but nothing's quite as humiliating as the bet he won - and lost - in 2008. Baldwin met teen star Miley Cyrus at a White House dinner in 2007, and the two started talking. Looking to get a new acting gig, Baldwin bet Cyrus that he'd get a tattoo of her initials. If he did it, she'd give him a role on the super-popular Hannah Montana. He got the tattoo, but Cyrus never paid off and the show went off the air in 2010 with Baldwin never appearing on it. That's gotta hurt.

Huck Seed, 2002

Professional gambler Huck Seed is well-known as one of the kings of the "proposition bet," willing to take up just about any ridiculous challenge if the price is right. Running down his list of accomplishments would take too long, so let's just share one great one. Seed was challenged to play four 18-hole rounds of golf at one of Las Vegas's toughest courses. In a single day. Using only a five iron, a sand wedge and a putter. Walking from hole to hole, with no caddy or golf cart. Oh, and he had to golf under 100 each round. Seed's opponent picked the hottest day of the year to have him do it, and Seed had two rounds over 100, but he managed to finish the day with four under and won a cool six figures.

Harry Bensley, 1907

The turn of the 20^th century produced some very amusing rogues looking to take advantage of a newly-connected world. Harry Bensley was a playboy and businessman who earned a healthy income from investments abroad, leaving him free to occupy his time with truly ridiculous bets. One evening in 1907, Bensley became embroiled in a discussion between financier J.P. Morgan and the Earl of Lonsdale as to whether a man could walk around the world without being recognized. To make a long story short, the two men wagered that Bensley couldn't circumnavigate the globe, wearing an iron mask and pushing a baby carriage the whole way. Dude spent six years trying to complete the task before stopping when World War I broke out. 

Emmet Bentley, 2012

Here's another particularly dumb tattoo bet, this one courtesy of our good friend Shaq. In 2012, Shaquille O'Neal announced over the air that he would give $1,000 to the first person who would get a tattoo of Charles Barkley smooching referee Dick Bavetta during the 2007 NBA All-Star weekend. A bartender in Santa Barbara named Emmet Bentley jumped at the chance, getting inked with the ridiculous kiss. Even funnier, when Shaq paid him off he bet him another grand that he wouldn't get a Mount Rushmore-styled tattoo of O'Neal and his cohorts on Inside the NBA. Needless to say, he took that one too.

Brian Zembic, 1996

These crazy bets sometimes do pay off for the gambler. High stakes poker player Brian Zembic took a bet in 1996 that he wouldn't get a pair of woman's breast implants put in and keep them for a year. If he pulled it off, he would rake in $100,000. Zembic went under the knife later that year and had a pair of perky 38C jugs put under his hairy chest. He weathered the criticism and kept the boobs in for the duration, even when the other gambler offered to buy him out early for $50,000. As of press time, he still has them in!

John Powell, 2010

The aspiring rapper known as Fatboy was performing at a house party in Crest Hill, Illinois and things were getting wild. So wild, in fact, that he decided to bet $5 that he could take a punch in the face from any girl at the party. 22 year old Tiffany Startz took the challenge, hauling back and clocking Powell right in the mush. At first, everything looked fine, but just minutes after the blow Fatboy crumpled to the floor. He was quickly rushed to the hospital, where he died as a result of a burst artery in his neck caused by blunt force trauma. Really not worth the five bucks, in our opinion.

Andrei Karpov, 2007

We've all heard stories about poker obsessives so desperate for one more hand that they throw all kinds of things on the table, but your wife? It happened - in Russia, of course. Andrei Karpov was deep in debt during a poker game with friend Sergey Brodov one cold night in Murmansk. After a quick inventory, he floated the idea of betting his wife on the next hand. Brodov good-naturedly accepted, but when Karpov lost the hand and his wife found out, she was so pissed off at him for even thinking about it that she divorced him... and married Brodov. Now that's a good sport right there.

Spud Mann, 2011

One last tattoo bet to really drive the point home, shall we? Some people take fantasy football way too seriously. Case in point: Omaha, Nebraska's Spud Mann, who started a league with nine of his friends where the last-place finisher had to get a tattoo agreed on by all the other members. Poor dumb Spud ended up with the lowest scores at the end of the season, and he was well and duly inked with a giant sparkly unicorn on his thigh and the words "FANTASY LOSER" underneath it. That's forever, dude.