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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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    • DJ Funktual profile image

      DJ Funktual 

      13 years ago from One Nation Under a Groove

      I really love 'Adventures in Babysitting' too, but that is the only one on your list that is a cult classic to me. The other three are pretty mainstream films.

      Wayne's World is based on SNL which is opposite of cult. Cult classics are movies that don't get a lot of advertising help from the studios because thay don't believe in the director's vision or method of filmmaking so they put little to no money into advertising it and then send it the video store. That's where a cult classic is born. It is nurtured by obsessive fans who tell all their friends and anyone else who'll listen that "You GOTTA see this movie!!!" But that' s only half the equation. 'A.I.Babysitting' was a vehicle (read: special inexpensive project to test a young unproven talent with carrying their first film.) for the lovely and talented Elizabeth Shue. She got this opportunity/vehicle based on her adorably conflicted rich girl in The Karate Kid. She pulled it off. I think the movie A.I.B. is genius! The cute little girl who idolizes THOR is a fresh take on hero worship. The scene I can't believe you didn't mention was the infamous, "Nobody leave dis w'thout sangin' da blues" which has so many great little nuances that it's still entertaining today. The other half of the equation as to whether or not you're a bona fide 'cult classic' is your film has to have made no money for the filmmakers initially, but over time as more people see it and it gets passed on by word of mouth, it becomes a well respected, but mostly unsung film and presto! You have a cult classic. A great example of cult classic is the movie "Office Space". Created by Mike Judge who had previously only done cartoon sitcoms on TV. (King of the Hill / Beavis & Butthead) The studio meeting went something like this, He said okay, "I wanna do a live version of my 'Milton' cartoon and I want creative freedom since I convinced my 'friend' Jennifer Aniston to be in it." The studio gasped and thought, 'wow J.A. has never carried a movie before and this guy's got her.' Deal. So Mike and Jenn started making fun of T.G.I. Friday's & Michael Bolton, and if there's one thing the studios don't like it's lawsuits. Both parties had to be pissed. Mike then got himself a great but cheap supporting cast. Buildings are being burned down by frustrated employees and that's it. The studio (and no doubt, Jenn's agent) wants bury to bury the movie with a quiet r elease on DVD.

      The rest is history. Gary Cole, who plays the rediculous Lumbergh went on to have a great career after his exposure in Office Space. And believe it or not, Michael Bolton now autographs copies of the DVD all the time even though they call him a 'no talent ass-clown' in the film. That's CULT baby!

    • Stacie Naczelnik profile imageAUTHOR

      Stacie Naczelnik 

      13 years ago from Seattle

      This comment is just to define my meaning of "classic cult movie" for the topic of this hub. My definition of one of these movies is one that has a "cult" like following, whether it is main stream or not.

      If anyone is intersted in learning about how to format their hubs, please check out the forums for help.

    • Stacie Naczelnik profile imageAUTHOR

      Stacie Naczelnik 

      13 years ago from Seattle

      How can you forget about The Breakfast Club? Hope it is happy nostalgia.

    • drbruce profile image


      13 years ago from Singaraja, Bali

      Ah, forgot about The Breakfast Club. You're getting me nostalgic about Chicago. Well done.

    • Stacie Naczelnik profile imageAUTHOR

      Stacie Naczelnik 

      13 years ago from Seattle

      Bob, I love Ferris! I think I've seen it the most times out of the others.

    • Bob Ewing profile image

      Bob Ewing 

      13 years ago from New Brunswick

      I have seen all of these and enjoyed them, perhaps Ferris, the most.

    • Stacie Naczelnik profile imageAUTHOR

      Stacie Naczelnik 

      13 years ago from Seattle

      You have to check out Adventures. It is classic 80s cult!

    • cgull8m profile image


      13 years ago from North Carolina

      I have seen 3 out of 4 all are great movies :), I will check out the Adventures in Baby Sitting.


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