Jennifer Love Hewitt, 2006 Oscars
Let me start by saying that Jennifer Love Hewitt (or more like her stylist) needs to learn how to use a curling iron. I get what she was going for at the 2006 Oscars — a tousled, curly bob, right? — but she should really work on her technique. And in case you were wondering, large pieces of hair sticking out is not sexy.