Ferris Bueller's Day Off (1986)

Brat Pack filmmaker John Hughes reportedly wrote the screenplay for Ferris Bueller’s Day Off (1986) in less than a week. But the epochal teen comedy has proven itself to be a classic — having been watched and rewatched many times since its initial release. The entirety of the film takes place on one day when smart-ass high schooler Ferris (Matthew Broderick) fakes an illness to play hooky with his girlfriend Sloane (Mia Sara) and buddy Cameron (Alan Ruck) in Chicago. During their ditch day, the trio visit some of the Windy City’s most iconic places from the Art Institute of Chicago to Wrigley Field. Ferris even lip synchs to “Twist and Shout” while riding on a float in a parade going through downtown. Look closely and you can see Hughes making an uncredited cameo as he runs through the streets. Meanwhile, Ferris’s jealous sister Jeanie (Jennifer Grey) and the principal Ed Rooney (Jeffrey Jones) try unsuccessfully to catch the truant in the act of cutting class. Of course, Ferris’s joie de vivre can’t be dampened even when everything comes to a crash via a 1961 Ferrari 250 GT California Spyder. The movie also includes Charlie Sheen, Stephanie Blake, Kristy Swanson, Cindy Pickett, Ben Stein, Louie Anderson, and Ms. Sara’s sleek physique. When the titillating teen dons a clingy wet negligee in the swimming pool, she really makes a splash on screen. If only Mia had used this day off to take her top off, then Mr. Skin would be splashing somewhere else!