The Rapper: John "Fatboy" Powell
The Bet: In May 2011, the little-known rapper from Illinois bet people at a party $5 that he could take a punch in the face from a girl.
The Result: He lost. And when we say he lost, we mean he lost. We'll be honest: We'd never heard of Powell, a member of some group called the Krazy Killaz, until this incident. But it's easily the craziest bet on this list. A woman by the name of Tiffany Startz eventually agreed to take Powell's bet, socked him in the face, and accidentally killed him. She's now facing reckless conduct and battery charges and he's dead. It was definitely not the way either of them planned on things going down.