3. Lil' Kim
Event: MTV Video Music Awards, 1999
As if Lil' Kim's breast's appearance on the red carpet wasn't enough, we still have flashbacks of the great Diana Ross cupping it on stage while the two presented the award for Best Hip-Hop Video. Unfortunately, this fashion trend didn't take off; our prom dates and brides will never wear formal attire that exposes their left breasts, no matter how many times we've asked.