Mark Polish as Henry McCarthy, a successful book author whose returning home to deliver a commencement speech to the new class of graduating high school seniors. Despite his success as a writer, being back in Sacramento has dredged up all of his youthful dreams, desires and disappointments, specifically his unrequited affection for the girl who is now the local pharmacist (Winona Ryder). Between run-ins with the outcast friends he left behind (Sean Astin & Josh Holloway), the school principal (Chevy Chase) and a seductive senior (Hilary Duff), Henry's sent spinning through a time warp that incites all the old emotions and challenges of the world he grew up in.