Starring Chicago: What Does a City Look Like on Screen?

Chris Barsanti
Eyes Wide Open
Published in
6 min readJul 6, 2023

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In 2001, the American movie industry was going through another of its occasional convulsions of reinvention. The splashy, brain-bending, pre-millennial oddities of 1999 (The Matrix, Being John Malkovich, Fight Club) were put to the side in favor of the industrial franchises just then gearing up. By the end of 2001, the Harry Potter and Tolkien movie machines were off and running. So was a late-blooming series based on a certain overperforming muscle car flick whose offspring would still be hitting multiplexes over twenty summers later.

As movies editor for citysearch.com’s Chicago node, I should have been covering that thundering shift in the moviemaking landscape. But I did not truly see what was happening. I could tell 2000’s Gladiator and X-Men foretold a new kind of spectacle filmmaking: grimmer, faster, and unromantic. I could see that 1990s’ auteurism was coming to an end. I wrote what I could, covering releases that Dave Kehr (the great longtime Chicago critic then working for citysearch.com in New York) didn’t get to or had little interest in, and interviewing the odd celebrity who came through town on the still-extant junket circuit. I was thrilled by Memento, weirdly defensive about criticism of A.I., and nonplussed by Mulholland Drive. But that spring and summer I was also looking more to the past than the present.

Earlier that year, I had started working with the The Film Center on a way to inaugurate their new facility when it opened in June as the Gene Siskel Film Center (named in honor of the Chicago Tribune’s critic and Roger Ebert sparring partner who had passed away in 1999). Relocated from a purposeful but unlovely location by the Art Institute to the heart of State Street, the Siskel was going to be the shiny arthouse theater the city deserved, an upmarket complement to more hardcore cinephile venues like Facets Multimedia and Doc Films. Our idea was that after the theater opened in June, it would spend its first three weeks showing people what Chicago looked like on screen. Citysearch.com would be a marketing partner and help with publicity.

We had ideas for getting attention. First was the 24-hour marathon to kick things off, because isn’t it best to watch Henry: Portrait of a Serial Killer through bleary eyes at three in the morning? There were celebrity guests: Bonnie Hunt showing her directorial debut Return to Me, because when one has the option of having Hunt in person, one takes it. Local critics were invited to screen a favorite Chicago movie, because who knew Ebert was going to select Love Jones? At some point, Garrett popcorn was involved, because of course it was.

Luckily, the Siskel’s programmer — as generous as he was impeccably film literate — kindly humored some of the ideas I threw his way. We had the good fortune to be planning such an event in Chicago. The city’s towering status in American history and pop culture, along with its visually striking mix of skyscrapers and tree-lined neighborhoods knitted together by the El and laid against a shimmering lake, made it the country’s most frequently filmed city outside of New York, Los Angeles, and San Francisco. A Starring Cincinnati festival would have been trickier.

We plotted out the offerings like a graph, with subject along one axis and style on the other. The idea was to present as broad a picture of the city as possible, given the constraints of time, limits of audience interest, and available movies. Celebratory to caustic. Suburbs to the South Side. We wanted the festival to be a filmic atlas of mood, time, and place.

That meant looking at Chicago from a historic perspective. The city’s great early black filmmaker Oscar Micheaux was represented by Within Our Gates (1920), its era of gaudy gangsters and adrenalized reporters covered by two Howard Hawks immortals (Scarface, His Girl Friday) and an earnest John Sayles corruption drama (Eight Men Out), and the convulsions of the Democratic National Convention given docudrama form in Haskell Wexler’s semi-real Medium Cool.

(Clockwise from top left) ‘His Girl Friday,’ ‘Medium Cool,’ ‘Within Our Gates,’ ‘Scarface,’ and ‘Eight Men Out’

For a theater like the Siskel, which was more given to Hou Hsiao-Hsien and Jean-Luc Godard retrospectives, showing mainstream fare seemed an odd fit. But the alternative, pretending that John Hughes and The Fugitive played no role in people’s imagination of Chicago, seemed even odder. There needed to be room for Ferris Bueller’s suburban escapism, gangster violence both calculated (Thief) and operatic (The Untouchables), and also experimental misfires that could still capture the city’s bebop postwar pre-hippie cool (Mickey One).

(Clockwise from top left) ‘Ferris Bueller’s Day Off,’ ‘Mickey One,’ ‘Thief,’ and ‘The Untouchables’

Plenty of genre movies have used Chicago’s backdrops interchangeably. But others brought a grit and texturing that resonated with those who knew the town. The previous year’s instant classic High Fidelity used a semi-romantic comedy template to examine the anxieties of North Side hipsters, Candyman threaded its horror conventions with some stinging commentary on city-specific class and racial divides, Cooley High infused its coming-of-age teenage narrative with autobiographical specificity, and Henry: Portrait of a Serial Killer used its low-budget grubbiness to present a street-level view of the city’s down-and-out side in the 1980s. (The same festival a decade later would have included Christopher Nolan’s The Dark Knight; no matter that it was meant to be Gotham City, the Loop’s grandeur remained unmistakable.)

(Clockwise from top left) ‘Candyman,’ ‘Cooley High,’ ‘High Fidelity,’ and ‘Henry: Portrait of a Serial Killer’

Some selections were just for fun. Greg Glienna’s 1992 original dark comedy Meet the Parents likely reminded many an audience member of a Wisconsin death trip in their past. Or Brian de Palma’s ludicrous telekinetic thriller The Fury, which used its Chicago locations beautifully but could ultimately have been set anywhere.

But each movie brought a different part of the city to life. LaSalle’s Art Deco grandeur, the modest beauties of the bungalow neighborhoods, the bucolic waterfront, the beat-down tenements, the look-the-other-way suburbs, the people’s prickly pride, the yawning gap between the haves and the have-nots, and the overlooked intelligentsia’s stiletto snark. It was all there at twenty-four frames per second.

Like all such events, the planning seemed to take an eternity and then it was over in a flash. But by the time it was over, we felt we had at least given the city its cinematic due.

The varying aspects of Chicago — its people, peculiarities, and personalities — which the festival did not show would take all day to list. It’s a big and roaring city, after all, packed with enough stories to fill a month’s worth of 24-hour marathons.

It just depends on filmmakers to shoot those stories.

This article was updated on July 6, 2023.

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