FERRIS BUELLER'S DAY OFF (1986)
The film follows high school senior Ferris Bueller (Matthew Broderick), who decides to skip school and spend the day in downtown Chicago. Accompanied by his girlfriend Sloane Peterson (Mia Sara) and his best friend Cameron Frye (Alan Ruck), he creatively avoids his school's Dean of Students Edward Rooney (Jeffrey Jones), his resentful sister Jeanie (Jennifer Grey), and his parents. During the film, Bueller frequently breaks the fourth wall by speaking directly to the camera to explain to the audience his thoughts and techniques.
Hughes wrote the screenplay in less than a week and shot the film—on a budget of $5.8 million—over several months in late 1985. Featuring many famous Chicago landmarks including the then Sears Tower and the Art Institute of Chicago, the film was Hughes' love letter to the city: "I really wanted to capture as much of Chicago as I could. Not just in the architecture and landscape, but the spirit."