The World's Most Outrageous Bets

Degenerate gambling can be a devastating scourge on family and friends. I know. It runs in my own family. With that said, there's also no doubt that the world of gambling has produced its share of memorable characters such as Benny Binion and Amarillo Slim. Not only are many of these characters known for being wizards at the poker table, some are known as masters of the "proposition bet." In gambling, a prop bet can either be a side bet within a specific game, or it can be a one-of-a-kind personal bet that has nothing to do with a specific game. An example might be as follows: you and a friend are standing at a bank of elevators in a building's lobby. You make a $5 prop bet with your friend that the second elevator in the bank will be the first to arrive on the ground floor.

And then there's the degenerate gambler's version of the proposition bet, and there have been doozies.

Amarillo Slim

Thomas Austin "Amarillo Slim" Preston Jr. is not only of the greatest poker players of all time, he's the king of the proposition bet. His 2003 book, "Amarillo Slim in a World Full of Fat People", describes some of the most unusual prop bets ever made.

He once beat pool legend Minnesota Fats at his own game using a broom instead of a pool cue.

He won $300,000 from country singing legend Willie Nelson in a game of dominos.

He even beat daredevil Evel Kneivel in golf, using a carpenter's hammer instead of a club.

And he beat tennis star Bobby Riggs at Ping Pong using a skillet instead of a Ping Pong paddle.

Phil Hellmuth and Huck Seed

World Series of Poker champ Phil Hellmuth made a $50,000 bet with fellow WSOP champ Huck Seed (an unlikely name for a hustler) that he couldn't stand up to his shoulders in ocean water for 18 hours straight. Seed took the bet and called it quits after three hours.

Huck Seed and Howard Lederer

Seed also lost a $50,000 bet with Howard Lederer after Lederer claimed that he could beat the 6'6" athletic Seed in a 50-yard dash while hopping on one foot.

Titanic Thompson