Henry McCarthy, the 30-something author of a popular 80s-themed novel, returns to his suburban hometown to deliver the commencement speech at his former high school. Despite his success as an author, Henry's return home has sparked all of the youthful dreams, desires and particularly disappointments he's never quite gotten over, specifically his unrequited affection for the girl who is now the local pharmacist: the elusive Scarlet Smith (WINONA RYDER). Between run-ins with the outcast friends he left behind Big Girl (SEAN ASTIN) and Wino (JOSH HOLLOWAY), the school principal (CHEVY CHASE) and a seductive senior, Shasta O'Neil (HILARY DUFF), Henry is sent spinning through a time warp that incites all the old emotions and challenges of the world he grew up in. Henry can only hope to "Stay Cool" and make it, once again, to graduation day.