Written in four days by director John Hughes (The Breakfast Club, Sixteen Candles), this love letter to Chicago follows the inventive title character, played by Matthew Broderick, as he ditches high school for the ninth time, taking his reluctant best friend Cameron (Alan Ruck) and girlfriend Sloane (Mia Sara) on a memorable series of escapades across the Windy City. The film features two hysterical antagonists: Bueller’s sister Jeannie (Jennifer Grey) and Principal Rooney (Jeffrey Jones), both of whom work doggedly to try to catch Bueller cutting school. With Broderick’s copious fourth wall breaks and the film’s abundance of quotable dialogue, Bueller’s influence is found throughout the fabric of popular culture. Still, it’s worth slowing down and taking a look at the original on the big inflatable screen, so you don’t miss it. — Lisa Elliott
