The Moment: Wayne singing his heart out when he was asked to "freestyle" during a 106 & Park interview
When It Took Place: June 2008
How Weird Was It? 3.5 OUT OF 5 MARTIANS. The funny part is that, looking back, this doesn't seem all that weird. Now, we know that Wayne enjoys singing ("How To Love," anyone?) and isn't afraid to do it. But, imagine if any other rapper started freestyling and then ended up singing a made-up R&B track. It was a really weird moment.