1999 : Lil ' Kim showed up at the 1999 MTV Video Music Awards with an entire breast exposed and only a tiny piece of fabric over the nipple . Kim 's outfit became even more controversial later when she appeared on stage with Mary J. Blige and Diana Ross to present the Best Hip-Hop Video award , and Ross reached over , cupped her hand under Kim 's exposed breast and jiggled it while Kim laughed
1999 MTV Video Music Awards
1999 MTV Video Music Awards
MTV Video Music Award