Lil Kim was at the height of her fame at the 1999 VMAs, so she could get away with wearing little more than a strategically placed purple pasty over her left nipple. But that didn't make it any less of a fail.

She took going braless to a whole other level. Even the iconic Diana Ross was in shock and couldn't resist feeling her up on camera.

Those patches of fabric on her elbow and shoulder could have been used to, you know, make the rest of her top.