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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. 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 and along with Matthew Lillard and Linda Cardellini.
He guest starred on the popular NBC show Friends as a sensitive male nanny named Sandy on the series' 200th episode.
Prinze starred in his own television sitcom, titled Freddie. He has starred in films such as I Know What You Did Last Summer (1997), I Still Know What You Did Last Summer (1998), She's All That (1999), Summer Catch (2001), Scooby-Doo (2002), and its sequel Scooby-Doo 2: Monsters Unleashed (2004).