34. Jessica Simpson
Jessica bounced back from last year's mom jeans debacle by embarking on a journey of self-discovery that was chronicled on her VH1 series The Price of Beauty. As she focused on her internal growth, there are always headlines on the topic of her love life after her birthday breakup from Tony Romo. Jess has since been linked to men like Jeremy Renner and Billy Corgan. Her ex-boyfriend John Mayer brought her some unwanted attention when he mentioned their sex life in Playboy, but Jess characteristically laughed it off. Jessica also expanded her retail empire with the introduction of new bags, shoes, and fragrances. Jessica had a slight PopSugar 100 dip in 2009, but she's once again back in the 30s, where she had a spot in 2007 and 2008.