Where: MTV Video Music Awards

When: 1990

Flavor Flav has rocked pretty wild outfits over the years, even showing up to the "Los Premios MTV Latin America 2008" Awards dressed as a bullfighter. But this ensemble trumps all: Flav attended the 1990 VMAs in straight Kanye West "Sorry I'm in pajamas, but I just got off the PJ" style—except he (probably) didn't fly private, and looked a lot less luxurious than Yeezy's lyrics sounded.