Top 10 Movies Set in Chicago
Written By: Andrew James
Sitting on a stoop in downtown Chicago the other day just shooting the breeze with my friend (while we waited for the women to get ready as always), he suddenly looked at me and blurted out, “I want a hard-target search of every warehouse, farmhouse, henhouse, outhouse and shithouse in the area.” Then with his best Tommy Lee Jones impersonation… “your fugitive’s name is Doctor Richard Kimble.” So he might’ve gotten the quote not quite right, but it was funny at the time and got me thinking what are some of the best movies set in Chicago. Sitting on the stoop we came up with several titles off the top of our heads.
Then of course, being the nut that I am, I spent a lot of Saturday at Lollapalooza thinking about Chicago movies and which of those would go on a top ten list. So yes, while Broken Social Scene was kicking some ass on stage, I was constantly reminded of my favorite Chicago movies. Check out the list I stuck under the seats…
Just to be clear, as always when I’m putting together my top ten lists, these are my favorites; not necessarily what I (or anyone) would consider the best or superior quality in film making. These choices might be on the list simply for a special place in my heart (or because I couldn’t think of any others).
10) WildcatsHere is a perfect example of a movie I can’t see appearing on too many top ten lists (maybe a top ten football movies or films about female empowerment), but I remember watching this when it first came out on video even though I wasn’t supposed to (strict parents) and loving it all the more for it. Quite the cast too if you look back on it (Hawn, Snipes, Harrelson, Mykelti Williamson and even ruce McGill as the evil, rival, head coach). Probably not particularly funny these days, so I’d prefer not to soil my memories by watching it again. But a fun movie back in the day.
9) Save the Last DanceHere is an example of the type of movies I can’t stand (the trailer for Stomp the Yard makes my skin crawl) - you know, white person learning from the urban punks to know what it means to have rhythm. But for some reason this one grabbed me. It takes a good natured kid out of her quiet suburban life and shoves her into a world she never thought she’d be a part of to sink or swim. Fortunately for the girl (and for us) she’s Julia Stiles and can move like nobody’s business. It takes elements of the arts that I don’t usually care for (ballet and hip hop) and fuses them together to make just the right recipe for a movie. Stiles sells it to me and I’ve been a fan ever since.
8 ) The Blues BrothersHere’s a film I admit to not having too much experience with. I’ve only seen it once and I was a lot younger then. Though I think the comedy was over my head at the time (or just not my style) I do remember the comedy based much around the Chicago area. I think I remember being told that the city is almost as much of a character as Jake or Elwood Blues were. Also Princess Leia is in it. Bonus. So while I don’t remember it all that well, I do recognize it for its broad audience appeal and high powered (and original) comedy.
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7) Eight Men OutOk, this one doesn’t have all that much to do with Chicago either. It just happens to focus on the baseball team of that city. And I have to admit just sort of having a soft spot for baseball movies (I even considered putting The Rookie on this list - yeah, the one about the 10 year-old who plays for the cubs because he can pitch faster than anyone). This one though, has a human message and great actors at the helm and goes a lot deeper than just the love of baseball. It actually is quite the stain on baseball. That’s ok though; I still love it.
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6) The StingI’ve only seen this once and completely loved it. The style and tone of Chicago in the 1930’s plays a big role in the feel and story for this one. Throw in Paul Newman, Robert Redford, Scott Joplin’s music, a good twist of an ending and a shitload of Oscar wins and you’ve got a movie that should probably be a lot higher on this list.
5) The FugitiveAs you probably didn’t bother reading above, this is the movie that inspired this list. Outside of the Trilogy franchises, this is easily among Harrison Ford’s best films. Plus one of Tommy Lee Jones’ finest performances (I think he won the Oscar?). Full of action, intrigue, mystery and all the what-have-you’s of a great cops/robbers mostly all thrown into the big windy city. Yeah, another one that should maybe be higher on the list. Until you see the titles that are higher on the list…
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4) High FidelityDid you know High Fidelity takes place in Chicago? I didn’t, until doing some research for this list. So as soon as I realized it does take place there (watching it again I guess it’s obvious), it was a no-brainer to shoot it straight up to near the top of the list. The movie that brings Jack Black into stardom, Todd Louiso into a hilarious role and John Cusack as… well, exactly what I picture John Cusack doing today was a staple picture of the new millenium and I can relate the hell out of it. Hell, the premise is making top five lists, making the perfect mix tapes and figuring out life as a late 20s. Not to mention hanging out at record stores; which is all I did back then and now I work at one! Shit, I even had a girlfriend who’s father died too young. So yeah, I can relate. Fab movie.
3) Adventures in BabysittingFinally. A movie where Chicago really is a main character. Arguably more so than any of the humans in the movie. So what if it’s not completely realistic or even slightly believable? It’s a completely enjoyable romp through the city with kids that take their roles and run with them… right off of a 30 story building. All you comic-book geeks looking for a Thor movie need not look any further than Vincent D’Onofrio in the role here. The one-armed Mr. Pruitt beats out any “one-armedness” that The Fugitive had to offer and Albert Collins not allowing anyone to leave the club without singing the blues has to be an all-time greatest scene. Ya think?
2) National Lampoon’s Christmas VacationA confession. I was planning on putting the original Vacation movie in here just for the scene where they have their hubcaps stolen in the hood. Then I realized that scene takes place in St. Louis; Chicago is only mentioned. I thought my whole list was ruined until I realized that the Griswold’s actually live in Chicago. So even though it might be cheating a bit, how can I not include one of the funniest movies of all time and one that can’t not be watched every year, come Christmas? Sure it all takes place in a house and Chicago is pretty much irrelevant for the story; but it’s funny as hell and puts the Griswold’s back on the map after their not so great outing to Europe. I laugh out loud several times no matter how many times I watch this movie.
1) Ferris Bueller’s Day OffJohn Hughes, during the height of his career, writing a movie for one of the best villains of all time in Edward Rooney and Matthew Broderick in the role of his lifetime. Another great gem from Hughes that showcases his home town of Chicago quite nicely while at the same time being witty, funny and exciting, but also focusses on what’s important in life (at least for a teenager) and getting at the angst and fear in many young people’s lives. No one did this sort of thing better than Hughes and no one has since. Yes, Ferris Bueller’s Day Off has become a staple in every young person’s life and is compulsively re-watchable. How often is this on cable while you’re channel surfing and how often do you surf right on by? A lot is the answer to the former, never for the latter.
Another great Chicago movie (though technically it doesn’t enter the city until the very end) is Planes, Trains and Automobiles.
Comment by Dave — August 7, 2008 @ 8:58 pm
Personally I’d include Dark Knight even though I’m sure many would disqualify it for not taking place in Chicago. In fact if we’re basing this on the use of location shooting it’s near the top.
Weather man is a good one.
The king of course is Medium Cool. A film that’s not just intimate in it’s portrait of chicago but also documents an important chapter of chicago history.
Comment by Rusty James — August 7, 2008 @ 9:40 pm
I just watched Doomsday. starts off slow, but eventually is overcome by awesomeness.
Comment by Goon — August 7, 2008 @ 9:52 pm
Weatherman has a great style, but I don’t care too much for the movie itself. Never seen Medium Cool.
I think The Breakfast Club takes place in Chicago too.
Comment by Andrew James — August 7, 2008 @ 9:53 pm
As for the Cinecast… we had scheduling issues, then I was in Chicago, now I’m sick as a dog. I promise an episode real soon.
Comment by Andrew James — August 7, 2008 @ 9:55 pm
I actually lived in a shitty apartment right on the other side of those tracks. They were almost but not quite right outside my back door. While watching the movie I pretended that Macavoy moved into my apartment after me.
Comment by Rusty James — August 8, 2008 @ 12:11 am
And didn’t Road to Perdition take place in Chicago?
Comment by swarez — August 8, 2008 @ 4:21 am
I definitely second THE UNTOUCHABLES though.
And I’d say the obvious, CHICAGO, except that I believe that film was actually filmed in Toronto…
Comment by Kurt Halfyard — August 8, 2008 @ 7:39 am
As for Untouchables, happy to see all the Costner love, but for some reason I’m not huge on that movie either. It’s alright, but never really grabbed me; despite the “great” cast.
If “Road to Perdition” is in Chicago however, then that was an oversight.
Comment by Andrew James — August 8, 2008 @ 8:13 am
Comment by Kurt Halfyard — August 8, 2008 @ 8:20 am
I don’t have any to add. I never pay much attention to where movies are located…unless it’s taking place in Vancouver or Vancouver is filling in for some other location.
Comment by Marina Antunes — August 8, 2008 @ 10:31 am
Comment by Kurt — August 8, 2008 @ 1:16 pm
Comment by Rusty James — August 8, 2008 @ 3:07 pm
Road To Perdition, no idea where this film takes place. It has gangsters though, so probably Chicago. Where did Frank Nitti have his office?
The Untouchables gets worse every time I see it. Funny enough, in the beginning I hated De Niros overacting, but with subsequent viewings he becomes the only entertaining part of a dull film. Good lines from Sean Connery keeps it floating as well.
And I agree Chicago is a horrible movie. One of the worst examples of the story going nowhere everytime a song starts. Is it really overrated? I haven’t met anybody who liked it.
Comment by Henrik — August 8, 2008 @ 3:15 pm
The Negotiator.
I mean, its good enough for General Grievous’ collection:
http://negotiator.ytmnd.com/
Comment by Good — August 8, 2008 @ 3:57 pm
The first time I saw Chicago I hated it. I’ve since flip flopped. In the theater I found it big and annoying and actually boring, and didn’t remember any of the songs just minutes after leaving the theater. On DVD I guess I found myself in the right mood and on second listen I was already familiar with all the songs and happy with them. I own it now. One of my most extreme movie flip flops, I can’t say I mind, I much prefer liking a movie then hating it, even if its a movie a lot of people don’t like.
Comment by Good — August 8, 2008 @ 4:00 pm
The Negotiator is alright, too bad they injected a lame plot. It should just have been the situation and 60-70 minutes long.
Comment by Henrik — August 8, 2008 @ 4:29 pm
Comment by Mercurie — August 9, 2008 @ 10:00 am
But have you seen Medium Cool? I think it pretty much owns the number one spot.
Comment by Rusty James — August 9, 2008 @ 10:59 am
Rookie of the Year is possibly the greatest movie ever, forget the Chicago criteria, I’m talking EVER. LOL, just watched it earlier tonight, it’s my ultimate cheer-up movie after a bad day. BTW, these are commonly confused, but “The Rookie” is the Dennis Quaid movie from 2002, and it was mostly set in Texas.
Excellent call on Adventures in Baby-Sitting and Ferris Bueller.
Comment by Ashley Townsend — August 10, 2008 @ 10:33 pm
Comment by Andrew James — August 11, 2008 @ 7:48 am
Comment by Rusty James — August 11, 2008 @ 2:33 pm
Comment by Kurt Halfyard — August 11, 2008 @ 3:48 pm
Comment by Rusty James — August 11, 2008 @ 4:01 pm
Comment by Andrew James — August 11, 2008 @ 4:09 pm
Comment by Ashley Townsend — August 12, 2008 @ 4:48 pm