The 12 Most Ridiculous Bets of All Time


By web gangsta | Published:

The Man with the $100,000 BreastsYou have probably seen the movie 21, about the MIT whiz kid blackjack players who figured out how to scam casinos for millions of dollars simply by counting cards and playing as a team.

Regardless of how glitzy the movie made it look, counting cards to make a living is not as easy as it seems.

Sometimes, gamblers need to have fun too – which is where proposition bets come into play.  What’s a proposition bet?  It’s a side bet of any type, usually of an uncommon event.

For example, people bet on the Super Bowl all the time – whether it be a Super Bowl grid or betting the line in Vegas based on who they think will win, or whether the point spread will be met.  A Super Bowl proposition bet are the more obscure items:

  • The coin toss
  • Whether there will be a kickoff return for a touchdown
  • Whether anyone will be heard swearing on the television broadcast

These aren’t necessarily tied to whether a team will win or lose the game, but rather what happens in the events surrounding the Super Bowl.  But a proposition bet doesn’t have to revolve around the Super Bowl or sports at all.  Sometimes, these bets are a bit more obscure and interesting.

Chicago Now has compiled what they feel are the TOP 12 MOST RIDICULOUS PROPOSITION BETS OF ALL TIME.   Some of these include:

  • Poker pro Howard Lederer, a vegetarian, earned $10,000 by eating a hamburger
  • Amarillo Slim made $40,000 by driving a golf ball over 1.5 miles.
  • Online poker player Jay Kwik was paid $40,000 after living in a Bellagio bathroom for just a few days
  • Brian Zembic, a professional backgammon player, was bet $100,000 that he wouldn’t be willing to get breast implants and keep them for a year.  Not only did Brian win the bet, he kept the implants for longer than the bet required.  (Brian is the subject of the book THE MAN WITH THE $100,000 BREASTS, a fine read that covers the background of this story as well as a few other gambling stories

If you are interested in placing your own proposition bet, you may want to consider visiting LONGBETS.ORG, a site where you can post and bid on bets of all types.