Gregson Wagner's first film role was as Lisa in the 1992 crime drama film "Fathers & Sons". She then had a small role in the movie "Buffy the Vampire Slayer". Following that film she starred in several TV movies including "Modern Vampires", "Hefner: Unauthorized", and "The Shaggy Dog". In 1995, she starred with her stepfather Robert Wagner in a "Hart to Hart" TV movie. She starred in the Wes Craven horror film "Mind Ripper". In 1996, she co-starred with Jon Lovitz and Tia Carrere in the comedy "High School High". She played Lou in the 1997 film "Two Girls and a Guy". Gregson Wagner played a small role in the 1998 thriller "Urban Legend". That same year she guest starred in an episode of "Ally McBeal" and co-starred with Vincent Kartheiser, James Woods and Melanie Griffith in Larry Clark's crime drama "Another Day in Paradise". To avoid an NC-17 rating, a rough sex scene with Kartheiser had to be removed from the theatrical version.