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.
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Week In PhotosKristin Cavallari launches her new jewelry line in Beverly Hills, Calif.,plus more of your favorite stars this week in photos.
Young HollywoodFrom Kaley Cuoco to Shia LaBeouf, where are yesteryear's young Hollywood stars now that they're (mostly) grown up?
Family FitnessCheck out Mario Lopez working out with his daughter, plus more celeb families who get athletic together.
Week in PhotosKatie Holmes arrives at the premiere of "Days and Nights" in New York, plus more of your favorite celebs this week in photos!
NestingAshton Kutcher makes a joke about his baby gear stockpile.Plus, more celebrity news for Sept. 25, 2014.
Hit or Miss?Fashion recap: Vote on September's fashion hits and misses.
Blended FamiliesFind out which celebs have step- or half-siblings ...
Awkward Much?Check out Kristen Stewart looking particularly uncomfortable, plus more stars' less-than-flattering red carpet poses.
Week In PhotosTaylor Swift arrives at the German Radio Awards, plus more of your favorite stars this week in photos.
Fashion OffendersLindsay Lohan, Cara Delevingne, and Rita Ora all get an F on this week's Fashion Offenders hosted by Wonderwall's Kirby Kristen.