Joel (Tom Cruise) is a teenager living in Chicago. He is a mediocre student and is in his last semester of high school and is determined to attend Princeton and have as much fun as possible beforehand. When his parents leave on vacation, Joel is left with the family’s upscale townhouse all to himself. Unfortunately he manages to total his father’s Porsche. Joel then has to somehow raise enough money to pay for the repairs to the car before his parents arrive home. To fund the repairs Joel manages to let his parents home out as brothel, with the charming prostitute Lana (Rebecca de Mornay) and incurs the wrath of her pimp Guido (Joe Pantoliano). Aided and abetted by his best friend Miles (Curtis Armstrong) Joel is thrown into a chain of events that are almost beyond his control.