The Chicago Movie Draft


Chicago has a rich movie tradition. People forget that, what with New York and Los Angeles doing the typical thing in believing they are each superior. There is something so gratifying about seeing the city on screen, flirting at times with accessibility and grandeur, polished for mass consumption yet gritty upon reflection.

Kevin Kaduk of Sports Blog 2.0 fame and founder of Midway Minute, a Chicago sports newsletter, was kind and passionate enough to collaborate on some premium niche content with us in the form of a Chicago movie draft. And to talk about it. A double-whammy.

Kevin Kaduk: Ferris Bueller's Day Off 

First off, I want to thank you for inviting me to take part in this draft. I think it's a noble exercise to remind the world that Chicago has contributed much more to the living culture than never-ending Dick Wolf procedurals.

Anyway, my first selection is Ferris. I can't tell if this is the easiest pick or the hardest one, which speaks to both to the allure of the first nice spring day in Chicago and the strength of the movies that we'll pick after this. Ferris has the Art Institute, an impromptu parade appearance down Dearborn and the voice of Harry Caray. It's hard to top.

Kyle Koster: Hoop Dreams

Steve James' 1994 masterpiece is a no-frills look at the audacity of hope and the crushing eventuality of long odds. It brought the camera into real, under-represented places and captured the unique place high school basketball had and still has in the city without extraneous poetry. Its imagery remains relevant; though the geography has changed there is still a clear delineation between the haves and have nots, the silver-spooned and those fighting to cash their golden ticket. 

Paul Kane/Getty Images

Kevin Kaduk: The Dark Knight

Hoop Dreams is such a great pick. It actually might be the best combination of both characters and city, though as you mentioned it's reality and the city that tragically wins out in the end. 

I'm picking Christopher Nolan's second Batman movie with my second choice. All these years later, I still can't believe Nolan took places we see every day and turned it into a vast and grim sandbox for the comic book characters we grew up with. It's the best comic book movie by a mile and the city's star turn is as memorable to me as Heath Ledger's Joker. 

Kyle Koster: The Fugitive

It's incredible how much better Chicago worked than New York and Pittsburgh in the next film. I have such an affinity for The Dark Knight because they filmed a large portion of it near the old Chicago Sun-Times building and Ledger would skateboard between takes and the role players would invariably be in line behind reporters when we went downstairs for some Chex Mix. 

At its core, The Fugitive is about having one's home ripped from them. Richard Kimble has no choice but to go back to Chicago, where he's built a happy life, to clear his name. There's such a fantastic mix of big and small set pieces. Dramatic rooftop chases are interspersed with the mundanity of peeling oranges and forging ID badges. The tenor and tone of law enforcement is pitch-perfect. You can close your eyes and imagine them all living in the same Edison Park neighborhood. The city is used so well, from the St. Patrick's Day Parade scene to an allusion to being smushed by a car on Lake Shore Drive. There's a real care and respect at work.

Kevin Kaduk: The Blues Brothers

It's funny you mention your memories of Ledger skateboarding because I love hearing about experiences people had while the movies were filming here. My high school English teacher was an extra in The Fugitive, a classmate tried out for the part of Henry Rowengartner, I'm still upset I didn't have at least one run-in with Jennifer Aniston during the filming of The Breakup. 

I don't think I know anyone with a great story to share about the filming of The Blues Brothers, but I have to say if I could choose any Chicago movie to be an extra in, it'd have to be that one (I'd be playing sax for Aretha). I'm also pleased as hell I was able to pick it in Round 3. 

Kyle Koster: Candyman

Since this is a safe space, I will admit that I've never seen The Blues Brothers. Is that the one where the train crashes through the wall?

This one will mess you up. John Singleton is about as terrifying as villians go and there's such a saturation of unease that even the plot-driving scenes are drenched in unease. Blight plays off light and the city gets to play to the grittiness New York City has long monopolized in cinema. On a personal note, one time I watched this while visiting across the street from Cabrini Green and lost all track of reality, resulting in one of the more viscerally powerful screenings to date.

JEFF HAYNES/Getty Images

Kevin Kaduk: The Last Dance

Yeah, I think I'm going to go here. While the 10-part series wasn't without its shortcomings, it was also one of the few great things to come out of 2020. ESPN doled out the film over five Sundays, giving those of us in Chicago a shared cultural experience we needed and a time machine to a time when the west side was truly the center of the sports universe. It's as essential a movie to understanding Chicago's history as, say, The Untouchables or Eight Men Out

Kyle Koster: The Untouchables

This is a superb choice and one that I wished I'd considered. 

Brian De Palma turned Union Station into the most beautiful place in all the world, a marvelous cinematic turn. The black and white represent the good and the bad, with the gray representing the confusion. Its both timeless and current, capturing a very specific time and energy in the city, one you can still feel on still nights.

Kevin Kaduk: Drinking Buddies 

We're getting down to the nitty-gritty here and the value picks. I don't want to make a misstep here.

There are a few great movies about being young in Chicago. But About Last Night has way too much Jim Belushi for my tastes and I've never been able to get fully onboard with High Fidelity being "a Chicago movie" after falling in love with the London-based book first. 

So let's go with Drinking Buddies, a true-to-life 2013 movie about love, relationships and helping your friends move from crappy apartment to crappy apartment on the North Side of Chicago. I was firmly in this target demo when the movie premiered and I'll be forever thankful it allowed Anna Kendrick the opportunity to eat her namesake dog at Hot Doug's.

Kyle Koster: Eagle Eye

This was on my list as well. Extremely underrated and relatable. Like they made a movie about a random person in that age group, in that spot, in that time. 

Admittedly a surprise choice here but much like its Metra neighbor Source Code, the action scenes are a truly delight and use the transportation infrastructure to perfection. I wanted to pick a movie where it was almost immaterially set in Chicago.

Kevin Kaduk: Above the Law

I honestly have no recollection of Eagle Eye ever existing, so I'll take care of that one while you catch up on The Blues Brothers

Honestly, it's not that great of a movie. But if you give me a chance to watch Steven Seagal running around 1980s Chicago fighting people in alleys with baseball bats, I'm going to take it every time. One of those "so bad it's good" movies that you'll never turn off if you see it on a movie channel. 

Kyle Koster: Backdraft

Film Twitter is going to have a field day with that one. Surveying my list it looks like I am light on the feel-good stuff. It's going to be a shame but I can't fix that.

There's something so cool — and it's clearly reflected in my list here — about this era of Chicago. Michael Jordan was becoming the most famous person in the entire world. So too was Oprah Winfrey. There was all this international focus descending on the city and when it got there it encountered this working class old-worldness. Few things make me as happy as the knowledge they made a movie about fires in Chicago and it somehow slipped under the radar as an allusion to what it's most known for. Considering you mentioned Dick Wolf and his procedurals at the outset, this is a fitting end point.