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Kirsten Dunst

Current age: 32

Career at 20: Just after Kirsten's 20th birthday in April 2002, she was busy promoting her blockbuster film Spider-Man, which hit theaters that May. She also started filming 2003's Mona Lisa Smile that Fall, working alongside Julia Roberts, Maggie Gyllenhaal, and Julia Stiles.

Relationship status at 20: After being linked to her Spider-Man costar Tobey Maguire in 2001, Kirsten dated Jake Gyllenhaal, whom she met through her Mona Lisa Smile costar Maggie Gyllenhaal. The pair dated from September 2002 to July 2004, at one point moving in together and sharing a dog.

Quoted at 20: In 2002, Kirsten was interviewed about Spider-Man and discussed the famous upside-down kiss scene: "We had that huge rain scene, which was so cold. That was pretty challenging, to act all romantic and like you were warm in the Summer rain or whatever time of year it was supposed to be. But really it was so cold."

Image Source: Getty / DON EMMERT
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