Ferris Bueller's Day Off (1986)
Call us biased, but when it comes to movie odes to American cities, all we can say is, "Sex and The City who?" Carrie's romance with New York doesn't hold a candle to Ferris' whirlwind tour of the Windy City. (How perfect, though, that the two stars are now husband and wife.) Hughes consistently set his films in his sweet home Chicago, but Ferris Bueller is perhaps his most sincere love letter. It still holds up as one of the most classic high school films of all time and manages to make a truant who could have been infuriating—He gets away with everything! We should be so lucky!—nothing but adorable. Plus, Ferris' steadfast dedication to his best friend, and his rivalry with the lunatic principal out for blood, has us rooting for him from beginning to end. Call the film juvenile, but at its core the movie's message still resonates: "Life moves pretty fast. If you don't stop and look around once in a while, you might miss it."