3. Diana Ross grabs Lil Kim’s breast
Rapper Lil’ Kim really turned heads in 1999 when she showed up at the award show wearing a one-sleeved jumpsuit and just a pasty covering her left nipple. When Diana Ross joined Mary J. Blige and Lil’ Kim on the stage to present an award, the former lead singer of the Supremes coped a feel. The little jiggle Ross gave the rapper’s exposed breast is a moment that will definitely live on as one of the most memorable from the VMAs.