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Brock Freakin' Hudson. Ya know, the reality star who dated Taylor and had a tattoo of his own face on his bicep. And, let's face it — THIS is one of the best scenes in teen movie history. While he's not starring in as many films as he used to, he has voiced Shaggy Rogers in a TON of Scooby Doo videos.
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Jodi Lyn O'Keefe
The 37-year-old played Taylor Vaughan, the most popular girl in school (who could win Prom Queen on the first day of her period!) Today, she stars on the TV series, Hit the Floor.
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Paul Walker
Dean Sampson may have been the sidekick in this movie, but he was also the gorgeous piece of eye-candy. Unfortunately, Paul passed away in a car crash on Nov. 30, 2013.
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Gabrielle Union
The 43-year-old played popular girl Katie. She later went on to land bigger roles in films such as Bring It On and, most recently, the television series Being Mary Jane. She's currently married to Miami Heat basketball player Dwyane Wade.
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Anna Paquin
Waaay before she portrayed Sookie on the HBO smash True Blood, the 34-year-old played Zack's younger sister, Mackenzie, who plucks Laney's eyebrows for the first time. She's now married to Stephen Moyer and the pair is parents to fraternal twins.
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Elden Henson
The 39-year-old played Laney's nerdy friend (and often her voice of reason), Jesse Jackson. Since then, he played Pollux in The Hunger Games: Mocking Jay Part 1 and stars as Foggy Nelson in the television series, Daredevil.
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Kieran Culkin
Ah, another Culkin kid making it big in Hollywood! The brother of Macaulay, 33, played Laney's nerdy younger brother, Simon Boggs. Recently, he appeared in Quitters and Scott Pilgrim vs. The World.
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Freddie Prinze, Jr.
The '90s heartthrob, 40, played Zack Siler, the hottie of all hotties, who accepts the challenge of turning Laney Boggs into Prom Queen. Freddie ended up marrying actress Sarah Michelle Gellar and the couple has since welcomed two children, Charlotte Grace and Rocky James.
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Rachael Leigh Cook
Oh, Laney Boggs! She played the nerdy girl in school who was told she's a "waste of perfectly good yearbook space." Today, she lends her voice to the TV series, Robot Chicken.
