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In his first leading role, the romantic comedy She's All That (1999), he was very successful at the box office. Subsequently, he had leading roles in Wing Commander (1999), Down to You (2000), Boys and Girls (2000), Head over Heels (2001) and Summer Catch (2001), most of which were generally disliked by critics In 2002, he played Fred Jones in the live-action film version of the popular cartoon, Scooby-Doo, and reprised the role in the 2004 sequel, Scooby-Doo 2: Monsters Unleashed, both alongside his wife Sarah Michelle Gellar.