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Ryan Phillippe Then

Phillippe put on the charm — albeit in a messed-up way — in Cruel Intentions, then showed off his dramatic chops in Antitrust and Gosford Park.

Image Source: Columbia Pictures
Read More Ryan PhillippeMoviesTVJosh HartnettJoshua JacksonJames Van Der BeekFreddie Prinze Jr.Nostalgia
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