The Rapper: Mos Def
The Bet: In May 2009, Mos said he'd put up $1 million on MF DOOM against Lil Wayne.
The Result: Um, we're not sure if Mos quite understands how betting works. In order to "bet a million dollars on DOOM against Lil Wayne," you need to be able to quantify each side somehow so that a winner can clearly be decided. So, in essence, Mos just made this statement to try and make a point. There was no real chance of him losing a dime off of it. However, we like the sentiment and we love the idea of Mos, of all people, betting more money than 50 Cent just bet. So we'll allow it and include it on this list.