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87. Lindsay Lohan

Lindsay endured another year of ups and downs, personally and professionally. She and Samantha Ronson finally called it quits after a rocky on and off relationship. Lindsay was spotted with a variety of guys and even publicly made out with a random French actor. She found it hard to find employment due to her erratic reputation — her movie Labor Pains went straight to TV, but she did manage to film a small part in Machete and has a new project, Inferno. She made headlines with a short, scandalous tenure as creative director of Ungaro and still is active with her 6126 line. She had trouble with the law after failing to take alcohol education classes required after a 2008 incident and was sentenced to spend the Summer wearing a SCRAM alcohol and drug monitor. To complicate matters, she's involved in an ongoing battle with her father, Michael, but she remains close to her mother, Dina, and best friend, younger sister Ali.

Image Source: Getty