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Katy Perry: 2000

"I love pinups," Katy Perry has told InStyle. "I've taken a lot of direction from those girls in cute little outfits caught in flirtatious situations--with a dog leash tangled around their legs and their skirts blowing up." For the multi-platinum singer this means blunt bangs, flawless cat eyes and Vargas girl lips. But as the dress-up queen has also posed as Queen's mustachioed Freddie Mercury, a denizen of Candy Land (in her "California Gurls" video) and as a variety of high school archetypes (at this year's Teen Choice Awards), it's safe to say we can expect some exciting new looks from the Teenage Dream star: "I can't always be a Betty Boop girl, or I'd want to jump off the Hollywood sign."

2000: As a freshman at Dos Pueblos High School in Goleta, CA, the blond (!) Perry idolized Freddie Mercury. (Photo: Seth Poppel/Yearbook Library)
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