The adorable freckle-faced moppet moved from toddler modeling to appearing in more than 60 commercials and doing daily duty on soap opera Another World. She then delighted Disney bigwigs and family audiences with remakes of The Parent Trap and Freaky Friday before widening her appeal with the oft-quoted mega-hit Mean Girls and a platinum pop album Speak. Breast implant rumors, supposed beefs with Hillary Duff and Paris Hilton over shared boyfriend Aaron Carter and Stavros Niarchos respectively, a falling out with her hot mess of a father, her romance with Wilmer Valderrama, seven years her senior, and photos exposing her extremely emaciated 2005 look are the first inklings of the tabloid fodder she will become. At 20, she declared she'd win an Oscar by 30. Instead, by 24, the it girl had a string of failed relationships with men and women (DJ Samantha Ronson), a reputation for causing production halts, a rap sheet that included DUIs and theft, multiple stints in jail and rehab and an ankle bracelet as an accessory. She attempted to make a comeback by baring all in a Playboy tribute to her hero Marilyn Monroe in 2011 and by making light of her scandals on Saturday Night Live and Glee last year. Unfortunately, 2012 saw her first big role in years, playing Elizabeth Taylor in Lifetime's biopic Liz & Dick, widely panned and her back in legal hot water when she fled the scene after allegedly hitting a pedestrian with her car and assaulted a woman at a club on another date.