The Date: May 2007
The Crazy Moment: In an effort to intimidate his Mexican opponent Oscar De La Hoya, Mayweather made his way to the ring wearing a sombrero. The fight also took place on Cinco De Mayo.
Why It Was So Wild: Maaaaaaaan, Mayweather was on one when he decided to do this. And to make matters worse, this was also the first time that Mayweather nabbed 50 Cent to escort him to the ring, which made for one hell of an entrance. Before the match even started, Mayweather was already in De La Hoya's head.