Year: 1999

In the late '90s, TLC was riding a tremendous wave of popularity. Their hit single "No Scrubs," which we can only assume is about the group's collective hatred of Zach Braff, was up for six awards. And though they only took home one moon man, the award for Best Group Video, they did unanimously win one unofficial award: The Best Dressed Group of the Night. T-Boz, Left Eye and Chili all looked ridiculously hot in their dominatrix-like VMA outfits.