No. 2 – Amy Winehouse
This year, Mr. Blackwell left Britney Spears off the list because "her personal life is in such upheaval." It's surprising that troubled singer Amy Winehouse, who has canceled all her public appearances on doctor's orders, was given no such pardon. What Mr. Blackwell refers to as "exploding beehives above ... tacky polka-dots below" must have been too much to ignore.