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Joel Goodson (Tom Cruise) is a tame high school student who lives with his wealthy parents in the North Shore area of suburban Chicago. His father wants him to attend Princeton University, his alma mater, so Joel participates in Future Enterprisers, an extracurricular activity in which students work in teams to create small businesses.
When his parents go away on a trip, Joel's friend Miles (Curtis Armstrong) convinces him to take advantage of his newfound freedom by having some fun. On the first night, he raids the liquor cabinet, plays the stereo loudly, and dances around the living room in his underwear and pink dress shirt to the tune of "Old Time Rock and Roll". Another night, he races his father's Porsche 928, despite his parents' explicit instruction to drive only his mother's car.
The following day, Miles suggests that Joel contact a call girl. Joel refuses, but Miles calls "Jackie" on his behalf and leaves Joel's address on ...