Top Ten Chicago Movies

Sun Times columnist Tom McNamee recently listed his choices for the 10 best Chicago movies of all time. This sounded like a fun exercise, so I came up with my own list before seeing his. Turns out I missed some obvious choices (“Ferris Bueller” and “High Fidelity”), and there are some movies I now need to see (“Hudsucker Proxy” and “Things Change”). He did have one stinker on his list: “Stranger Than Fiction”, which I didn’t even remember being set in Chicago.

My own criteria are simple: A great Chicago movie doesn’t need to be a great movie, but it does need to have Chicago and its landmarks as one of its main characters. Both quantity and quality of landmarks matter here. Movies with Wrigley Field, the Loop, and Bonnie Hunt are better than ones with just a passing shot of the Daly Building or Jim Belushi. Perhaps the best way to describe it is that this is a list of the best Chicago movies, not the list of best movies set in Chicago.

So here’s the list. They are in no particular order, except that The Blues Brothers must be number 1.

[Blues Brothers section]

1. The Blues Brothers (1980). Can there be any question that The Blues Brothers is the best Chicago movie of all time, based its remarkable achievement of trashing so many iconic Chicago spots in so many different and innovative ways? It is the John Wooden of Chicago movies, if John Wooden lacked class. I say this protected from the safe confines of time, distance and memory, having not seen it in about 25 years. I’ve seen enough other movies I loved in high school (“Better off Dead”, “Meatballs”) to know that I should never see this movie again, so it will always remain perfect.

[Suburban Kids Having Adventures in the City Section]

2. Ferris Bueller’s Day Off (1986). Let’s face it – we all wanted to vicariously live the life of smart alec and nice guy Ferris Bueller. He skips around town on his final school sick day, taking in a Cubs game, a St. Patrick’s Day parade, and saving his friend from melancholy. Also, rather than give John Hughes his own section, this entry will also represent all John Hughes teenage angst movies.
3. Adventures in Babysitting (1987). Chris Columbus’ debut, about a babysitter traipsing around town trying to get her friend home to the burbs with babysittees in tow. Any movie with Elizabeth Shoe sliding down the diagonal-shaped roof of the Smurfit-Stone building is a great Chicago movie in my book.
4. Risky Business (1983). So, now I’m dating myself by putting in three 80s movies about suburban kids, but c’mon, how could I not include the heartwarming story of an innocent Tom Cruise, who hires prostitutes to sell to his friends in order to pay for repairs to his parents’ Porsche that he drove into a lake while they were gone? If that isn’t a typical American feel-good story, and a great Chicago coming of age story to boot, I don’t know what is.

[Romantic Comedy Section]

5. High Fidelity (2000). Even though this was a Nick Hornby novel set in London, John Cusack and Chicago make it their own. Plus, it unleashed Jack Black onto the wider world. Cusack wanders around town looking for old girlfriends and records to buy and produce, and it works as both a movie and a tour of the north end. I can still almost smell the musty, weedish record store he owned.
6. Return To Me (2000). A film that would otherwise only make a top ten list of guilty pleasures, there’s nonetheless something about this movie that tugs at my heart in a girlie sort of way. Bonnie Hunt (who wrote and directed) pretty much sums it up when she barks at Jim Belushi: “Grace has Bob’s dead wife’s heart!” In addition to Hunt and Belushi, it’s got large helpings of the Grant Park zoo, quaint Chicago neighborhoods, a charming Minnie Driver, and an incredible helicopter shot at the beginning where the camera swoops into the city and down onto the platform of a newly erected high rise.
7. While You Were Sleeping (1995). Another Chicago neighborhood movie, and curiously satisfying in the way it throws what would have been a typical Peter Gallagher character under a Metra train and keeps him unconscious for most of the movie. Mostly, though, it has Bill Pullman at the top of his ordinary guy game, making all us other ordinary guys feel like we don’t have to be Keanu Reeves or Brendan Fraser to have a shot at Sandra Bullock, if only our brother would get thrown under a Metra. Then, later, we could save the world from aliens as President. I knew people would eventually wake up (heh heh) and notice that Bill Pullman was just one of us ordinary guys, rather than a leading man, but it was nice while it lasted.

[African American Section]

8. Barbershop (2002). I’m revealing my white person bias by not including/remembering/knowing about more movies that present the Chicago African American experience. Guilty as charged. But I enjoyed Barber Shop quite a lot, where Ice-Cube desperately wants to do anything in life except what his neighborhood needs him to do, which is keep his barbershop open. It also includes a comprehensive series of the funniest and most unsuccessful ways to open a stolen ATM machine.
9. Hoop Dreams (1994). This Documentary doesn’t really fit my list, because it is actually an important, quality film. Nonetheless, it was set in Chicago, so must be included, I guess as the exception that proves the rule. It follows two inner city high school basketball players who are recruited in junior high to play basketball for a white suburban high school team, and proves the old adage that truth is often more interesting than fiction.

[Gangster/Thriller Section]

10. The Fugitive (1993). Tommy Lee Jones chases Harrison Ford around Chicago and Northern Illinois, while Ford looks for the real killer of his wife. A fine, fine chase movie.
11. The Untouchables (1987). I don’t actually remember much about this one, except that any list of great Chicago movies should have one with a scene of Robert DeNiro (as Al Capone) bashing someone’s head in with a baseball bat over a dinner table filled with gangsters.
12. The Sting (1973). Nothing says Chicago like a small time con artists scamming a big time crook. There are probably only a few scenes in this one that were actually filmed in Chicago, but hey, when I was a kid and saw it for the first time, I believed.

So there you have it. My top ten list of the best Chicago movies of all time, which I’m quite proud to have contained in only 12 entries.

After looking it over, and noticing the large number of low-rent movies I’ve included, I guess you could complain that I don’t have a very high opinion of Chicago. But you’d be snooty for thinking so. Chicago may not be as classy as New Yorkor as fashionable as LA, but it does provide more real people having real conversations over pizza and beer than NY and LA combined. In fact, this probably explains why they find it so entertaining to watch their landmarks get trashed by desperate bluesmen.