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Classic Cult Movies Set in Chicago

Updated on February 20, 2008

The four movies listed below have a few things in common. First of all, they were all set in the Chicago area. These comedies are also serious cult movies with great fan bases. In fact, I’m sure you have even heard of a few drinking games for these movies. Sure, these movies are getting to be on the older side, but they are timelessly amusing.

Do you agree with the picks listed below? Let me know what you think by leaving a message in the comment box at the bottom of the page. If you think I left a vital movie off of this list, don’t be shy: let me know!

Ferris Bueller’s Day Off

This 1986 high school movie is a fabulous comedy about a teenage boy who plays hookie from school. Ferris Bueller (Matthew Broderick) tricks his parents into thinking he is sick, and then takes his friends on an adventure around Chicago. The crazy school principal is intent on catching Ferris, so the movie really takes you on a ride. Luckily, Ferris is ridiculously charming and clever enough to get himself out of trouble.

Wayne’s World

Excellent! Wayne and Garth put on a TV show every Friday night from Wayne’s basement. Sounds like a winner, right? Then, a network executive in Chicago puts Wayne’s World on a national station. Wayne and Garth are no longer living in their sheltered little lives. Will they succumb to the evil the world has to offer? Or, will they stay strong and bombard the audience with their silly lines? You’ll have to watch to find out. If you don’t know who stars in this 1992 movie…then your head must be in the sand. (Okay, okay, it stars Mike Myers and Dana Carvey.)

Adventures in Babysitting

This 1987 movie is the best adventure movie that involves a night of babysitting ever. It is totally unrealistic and crazy, but it rocks. Elizabeth Shue plays the babysitter, who ends up dragging her charges on an adventure to rescue her friend from the inner city. The movie includes car thieves, cheating boyfriends, and superheroes. What more could you ask for in a movie?

The Breakfast Club

This is the classic 80’s movie (1985, to be exact). You’ve got five high school students—each one represents a stereotypical high school student—serving detention together in the school library. They have a day full of adventures that eventually lead to bonding. They leave detention as different people. So, you don’t really get to see much outside of the school, but it is set in a fictitious Chicago suburb. The usual 80’s suspects show up in this movie: Molly Ringwald, Emilio Estevez, Judd Nelson, Anthony Michael Hall, and Ally Sheedy.

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