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KATHERINE HEIGL Ever the trailblazer, Katherine must have a soft spot for push-the-envelope plots. She played Gerard Depardieu's daughter in 1991's My Father the Hero, in which she pretends her dad is her lover to grab the eye of a much-older crush.
SCARLETT JOHANSSON
It's hard to believe that Scarlett had an awkward stage. But you only have to time warp back to 1997, when she nailed the role of a snotty sister in Home Alone 3.
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JAKE GYLLENHAAL
The Oscar-nominated actor launched his career at the age of 11 in 1991, playing Billy Crystal's son in City Slickers. From the adorable looks of him, Jake must have been breaking prepubescent hearts.