The Rapper: 50 Cent
The Bet: No money was on the line, but in September 2007, Fif said that if his album, Curtis, got outsold by Kanye West's album, Graduation, which was dropping on the same day, he'd retire from the rap game. Gambling with your gamble? Now, that's G!
The Result: Kanye easily outsold 50. Yet, last we checked, 50 is still rapping. Hmmm...Not that we're complaining, but you do know how to make good on your bets, right, Fif?