Year: 1999

Lil' Kim caused a stir when she arrived wearing a purple sequined pantsuit with one distinct piece of the outfit missing: the piece that covered her left boob. Yep, save for a matching purple pasty that couldn't have been much bigger than a silver dollar, Lil' Kim was a lil' topless. 

Later, when Kim and Mary J. Blige presented an award with Diana Ross, Ross opted to greet Kim not by shaking her hand, but by jiggling her breast. It was an unforgettable moment. We're just upset that the greeting didn't take off, rendering the handshake obsolete.