David Simkins (written by)
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1 July 1987 (USA) more
Chris Parker (Elisabeth Shue), a high school senior, agrees to babysit Sara Anderson (Maia Brewton) after her boyfriend Mike Toddwell (Bradley Whitford) cancels their anniversary date. Sara's older brother Brad (Keith Coogan), who has a crush on Chris, decides to stay home and hang around. When Chris' friend Brenda (Penelope Ann Miller) calls from a Chicago bus station, having made a failed attempt to run away from her family, Chris reluctantly takes Sara, Brad, and Brad's sex-obsessed best friend Daryl Coopersmith (Anthony Rapp) from their safe suburban surroundings into the city to rescue her. A flat tire on the highway with no spare and Chris' realization that she has failed to bring her purse launches the group into a series of unlikely predicaments, including detainment by a car theft ring (from which Daryl steals a Playboy magazine filled with incriminating notes), pursuit by the criminals, a blues club where they're forced (by Albert Collins) to sing of their ordeal before leaving, a gang fight on a train which leaves Brad slightly injured (as well as a moment at a hospital where the others are briefly led to believe Brad is dead), and a final incident with their pursuers on the Smurfit-Stone Building in Chicago.