The Date: November 16, 2011
The Moment: A video surfaced of Wayne practicing several tricks—on a ramp that he had built on the roof of his Miami mansion.
Why It Was So Crazy: On the roof, son? First of all, it's crazy that you have a ramp on your roof. And, secondly, we're sure you're in no actual danger, but practicing on the roof just sounds like a dangerous place to skate. This is crazy on all accounts.