The Date: January 2010
The Crazy Moment: Diddy reportedly had to stop Mayweather from getting into a fight with rapper Rick Ross outside of a club in Las Vegas. The two had exchanged verbal jabs with one another because of the beef between Ross and Mayweather's friend 50 Cent.
Why It Was So Wild: The thought of Diddy of all people trying to stop a fight between one of the best boxers of all-time and one of the biggest rappers in the game is just funny to us. But we salute you for playing the role of the peacemaker in this situation, Puff.