Where: MTV Video Music Awards
This is possibly one of the most memorable moments in VMA history: Lil' Wayne in women's jeggings. Weezy already had people talking before it was confirmed that he was indeed wearing women's pants because said pants were so tight. But once the news hit, the Internets had a field day—someone even made a Lil Wayne Jeggings Twitter account. Years after the fact and it's still equally hilarious and terrible.