Olyphant made his feature film debut in "The First Wives Club" (1996) as an eager young director who attempts to cast Elise Elliot (Goldie Hawn) – who thinks she will be playing the leading lady – in the role of the elderly mother. Airing on the same day of that film's release, he made his television debut in the pilot of the CBS spy series "Mr. & Mrs. Smith". In 1997, Olyphant made a guest appearance as Officer Brett Farraday in three episodes of the ABC police drama "High Incident" and returned to New York's Playwrights Horizons to play a supporting role in "Plunge". He also had minor roles in the romantic comedy "A Life Less Ordinary" and the CBS television film "Ellen Foster". Olyphant's most high-profile role of 1997 was as a film student in the successful horror film "Scream 2", bringing "a degree of wild-eyed flair to the role," according to "HitFix"s Chris Eggertsen. He later described the role as "a gift. I had virtually nothing on my resume at that point. I'm sure some of it was made up."