The Date: September 6, 2011
The Moment: Wayne made a stop at Rob Dyrdek's Fantasy Factory and allowed Dyrdek to pull him on a go-kart while he was standing on a skateboard in order to launch him into a foam pit.
Why It Was So Crazy: This particular moment didn't really have anything to do with Wayne's skating skills. But it was still crazy nonetheless. If he hadn't made it into the foam pit, there's a good chance he could've gotten really hurt. After the trip, Dyrdek's associate Drama also pointed out that Wayne had gotten "noticeably better" at skating since the last time he'd made a trip to FF.