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James Van Der Beek, 'Dawson's Creek'

Then: Dawson Leery, idealistic hopeless romantic with telling long fingers and a strangely Oedipal thing for Katie Couric. Wore lots of flannel, tried every hairstyle imaginable to avoid looking 40. Did not get the girl. Now: Internet meme and surprisingly #FF-worthy tweeter at @vanderjames. You can catch him playing himself on ABC's comedy "The B---- in Apartment 23." (If he didn't have a wife and kids, and spent most of his time wearing Dawson-esque flannel and referencing Paula Cole to pick up girls.) ABC/WB
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