Ferris Bueller's Day Off (1986)

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Let the joyride continue! When high school senior Ferris Bueller fakes a sick day to run around Chicago with his best girl Sloane and his best friend Cameron, anything can happen. They twist and shout their way all around town, while staying one step ahead of their suspicious principal and Ferris’s envious sister.

Ferris Bueller (Matthew Broderick) is a tricky but harmless fast-talker. But he knows how to have fun, which is exactly what he sets out to do when he feigns illness and talks his parents into letting him stay home from school. The perpetually lucky Ferris enlists his hypochondriac best friend, Cameron Frye (Alan Ruck), into springing his girlfriend, Sloane Peterson (Mia Sara), from class, and the three embark on a raucous downtown Chicago adventure. From Wrigley Field to the Art Institute of Chicago to a Polish pride parade, Ferris and his friends make the most of their day off. But Ferris, Sloane, and Cameron might not get away with playing hooky. Ferris`s sister, Jeanie (Jennifer Grey), is determined to prove that Ferris is faking sick and make him pay for it, and the bumbling school dean, Ed Rooney (Jeffrey Jones), is sure that Ferris is pulling a fast one. Another classic from writer-director John Hughes (SIXTEEN CANDLES, THE BREAKFAST CLUB), this film features a star turn from Broderick as the charismatic Ferris. Watch for Charlie Sheen as the juvenile delinquent in the police station and comedian Louie Anderson in a brief appearance as a flower deliveryman.
Conniving Shermer, Ill. high school student Bueller spends his ninth school absence in the company of his kvetchy best friend Cameron and girlfriend Sloane, tearing through downtown Chicago on a mad quest for fun. The ruse seems perfect, right down to Cameron`s dad`s "borrowed" Ferrari, but Ferris` nemesis, high school principal Ed Rooney, is determined to bring the truants to justice.