The Date: December 2011
The Moment: During a tour in Australia, Wayne had a ramp set up on stage and routinely skateboarded right during the middle of his shows.
Why It Was So Crazy: Wayne really put himself out there. If he fell and busted his ass on stage, you know that video would go viral in, like, 5 minutes. So he took a risk every time he brought a board with him on stage.