2003—1998's The Parent Trap showcased two Lindsay Lohans, but the starlet has since grown out of her supercute Disney phase and shown even more sides of her personality. Those who wanted to see all of Lohan got their chance when photos surfaced of her getting out of a boat in Venice, sans underwear. And despite a recent court order requiring her to wear an alcohol monitoring ankle bracelet, Lohan will be posing nude for advertisements for her handbag line, possibly with her bracelet on. So, not totally nude then.
Jeffrey Mayer / WireImage
Last Weekend—Miley Cyrus may be one of Disney's biggest stars, but kids with Googling power might be seeing a bit too much of her lately. Blogger Perez Hilton sparked a media firestorm when he tweeted a link to an alleged "upskirt" photo of the 17-year-old without underwear. Hilton claimed the image was Photoshopped and soon fired back by tweeting a photo of Cyrus in an, um, risqué, position at the MuchMusic Awards. All this came in the same month Cyrus kissed a girl on Britain's Got Talent. When does shooting resume on Hannah Montana, anyway?
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2000—Although it's easy to forget it now, Christina Aguilera got her start on Disney's The New Mickey Mouse Club in 1993. She broke out onto the national stage as a singer in 1998, and while the singer is now married with an 18-month-old son, there are a few things Aguilera might want to keep mum about. She had a few feuds with women, but Eminem singled her out in "The Real Slim Shady" as giving him a sexually transmitted disease when she was only 19. Earlier this month, Aguilera told Company magazine she's attracted to girls. In a separate interview with Out magazine, the singer said, "My husband knows that I get into girls. I think it's fun to be open and play. The line is real to me."
Damian Dovarganes / AP Photo
2005—At 17, Rihanna signed on with Def Jam records and released her first single, "Pon de Replay," in 2005. New York magazine has since questioned whether her cookie-cutter look was her real personality at the time. With the release of an album titled Good Girls Gone Bad, everything changed. In early 2009, Rihanna was involved in a domestic abuse incident with then-boyfriend Chris Brown. Brown pleaded guilty to charges of domestic violence, but her image was tarnished as well. Later that year, nude photos of the singer—which she said were intended for an unnamed boyfriend—were leaked, pushing her even further away from her original good girl image.
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2006—Disney seems to have a talent for picking the young hellcats: High School Musical star Vanessa Hudgens has had naked photos leaked not once but twice. In fact, one batch of the leaked photos were taken when she was just 17. She apologized to her fans after her first nude photo scandal—when she was 18—but Hudgens appeared to not care about having such a squeaky-clean image by the time she hit the ripe old age of 20, when the second set of photos were leaked.
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2009—Oh, Cindy Lou Who, how you've changed! Gossip Girl star Taylor Momsen—who played Cindy Lou Who at the age of 8 in How the Grinch Stole Christmas—is now, at all of 16, attempting to prove herself as a bona fide sex symbol. Momsen has slammed people who say she should clean up her act, saying she "didn't get into this to be a role model for 7-year-olds. I have no interest in doing that, you know? If parents don't like some of the stuff I do then they shouldn't let their kids watch me."
Evan Agostini / AP Photo
1999—It's hard to remember Paris Hilton before her sex tape scandal, and for good reason: Hilton was only 19 when she and her then-boyfriend recorded themselves in a Las Vegas hotel room in flagrante. Turning the situation around, Hilton managed to profit from the tape. Although Hilton is now 29, she has never been able to shake the bad-girl image.
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