6. Ronaldo

Lifespan: 2002 World Cup
Reminds us of: A guy who picks up trannies. Oh, wait...

It was a nice contrast: The greatest footballer in the world picked the worst haircut in the universe to sport during the 2002 World Cup. Then again, Ronaldo put Brazil on his back and won them the tournament, so he should be able to do what he wants. But this is pushing it.