Illinois, if you’ve never heard of it, is the state that contains Chicago.
That’s a somewhat unfair, but undeniably accurate way to define Illinois. Those living in “Southern Illinois,” loosely defined by most Chicagoans as “Anything south of the Chicago burbs,” tend to have a somewhat complicated, contentious relationship with the big city, and to feel underrepresented as a result. It’s true—they are grossly underrepresented in the media and in the arts, especially when it comes to film. Still, around 75 percent of the entire state’s population can be found residing in Chicago’s greater metropolitan area. The obsession is understandable, and it means that a lot of the films to truly capture the Illinois ethos are set in or feature Chicago.
And let’s face it—when it comes to films, the beautiful Chicago skyline has always been a magnet, whether or not the city’s mayor in each generation has been particularly welcoming to Hollywood filmmakers shutting down the streets. This potentially cost a few films a spot on this list—let’s say, something like My Big Fat Greek Wedding, which is proudly set in Chicago’s classic Greektown, but did most of its actual filming in Toronto. Sorry guys, gotta dock you for that. Other films like Mean Girls incidentally take place in Illinois, but were you even aware of that before reading this? Its Illinois location in no way factors into the heart and soul of the film, so it’s not on the list either.
And yes, just so you know, there are indeed some films on the list that don’t take place in Chicago, that manage to capture the ebb and flow of smaller-town Illinois life. These 20 movies, taken as a whole, paint a picture of a vibrant but oftentimes gritty state, full of opportunity but also a twist of danger and corruption. These films can all be found in the shared mythology of my home state.
1. The Dark Knight
Gotham City is by no means located in Illinois, but everyone knows that in terms of its depiction, Chicago is the true heart and soul of Batman’s hometown. This movie, more than any of the others in the series, just reeks of Chicago, with dozens of iconic locations featured. Indeed, Nolan barely seems interested in disguising all of the landmarks, from putting the headquarters of Wayne Enterprises in the Richard J. Daley Center to staging the Joker car chase sequence on lower Wacker Drive where The Blues Brothers zoomed by on their Bluesmobile 28 years earlier. That’s of course just the beginning: the Sears Tower, Navy Pier, Trump International Hotel and Tower, The Berghoff and Randolph Street Station can all be seen, among others. Although some city residents probably wouldn’t like to admit it, the characterization is appropriate on multiple levels, given the story of vigilantism vs. the city’s history with and connections to organized crime. The connection between Gotham and Chicago goes beyond the visual and dives straight into the gritty heart of a city that has historically often had something insidious bubbling under the surface.
2. The Informant!
Director: Steven Soderbergh
It was pretty much impossible for me to miss this one, given that I spent four years working at the newspaper in Decatur, Ill., where the film takes place. Matt Damon stars as a real-life, decidedly non-movie star white-collar executive named Mark Whitacre who turned FBI informant against his employer, aggro-business giant Archer Daniels Midland, to reveal a price-fixing scandal. Rather than a straight comedy, though, The Informant! is rather a fascinating entry into the mind of a singularly odd man, one who tried to scam the FBI even as he was providing them information and ended up in jail right alongside his bosses. It features plenty of on-location scenes in Decatur, a mid-size, blue-collar city that is indicative of Illinois’ past prominence in the manufacturing industry. It’s a good look into the kinds of cities that dot the interior of Illinois, islands of buildings surrounded by fields of corn and soybeans, where Chicago is all-too-often considered a sort of separate province supposedly populated by the effete bourgeois. And I say this as someone who once attended a press conference where a state legislator introduced a proposal to split Chicago off into the 51st state of the Union so the good and decent folks of Central Illinois could live their own existence.
3. Eight Men Out
Director: John Sayles
Growing up in the southern Chicago burbs, the White Sox were my MLB team, and the experience of being a ChiSox fan is a crash course in the history of infamy. It’s weird to think of something that happened almost 100 years ago in a team’s history profoundly affecting that team’s identity even to this day, but believe it or not, there are still people in that area who feel passionately about the 1919 “Black Sox” scandal, wherein eight players conspired at different levels to intentionally lose the World Series at the behest of gamblers. The film, based on Eliot Asinof’s classic 1963 book, explores the complex motivations that drove some players knowingly into the ruse, such as pitcher Eddie Cicotte, in rebellion of a pinch-penny team owner, Charles Comiskey, who barely paid his players a living wage. David Strathairn is wonderful as Cicotte, the lynch-pin to the scandal, as is John Cusack as Buck Weaver, the idealistic player who refuses the participate in the fix but still ends up banned for life from baseball anyway. In a city famous for corruption, the Black Sox scandal has always been a dark spot on Chicago’s sporting history, a persistent reminder of the nefarious forces operating in the shadows to undermine even something as pure as the national pastime.
4. A League of Their Own
Director: Penny Marshall
And just to show that Illinois baseball movies don’t necessarily have to be depressing as hell, A League of Their Own also takes place in the Prairie State. The Rockford Peaches hosted the likes of Geena Davis, Rosie O’Donnell and Madonna in this charming 1992 comedy-drama, today remembered primarily (and understandably) for one of Tom Hanks’ most colorful supporting roles as the team’s alcoholic manager, Jimmy Dugan. The film showcases Illinois as an archetypal Midwestern state during a period of change, especially as far as gender dynamics were concerned. With men such as the husband of Davis’ character away fighting World War II, women were being thrust into the workplace and even the sporting arena in a wave of unexpected, often unwanted progressiveness. The foundations laid in arenas so seemingly insignificant as a baseball stadium had a direct correlation with the rise of second-wave feminism in the 1960s, both in Illinois and the nation as a whole.
5. White Heat
Director: Raoul Walsh
The trope of the Prohibition-era gangster is more heavily ingrained in Chicago than any other city in the country, to the extent that Chicagoans traveling abroad often find that the first reaction of people on the other side of the world to the phrase “Chicago” is references to Tommy Guns and Al Capone. The criminals who more or less ran the city in the Roaring Twenties have been a fixture of populist imagination ever since, especially in ’30s and ’40s Hollywood, and especially at Warner Bros., which built its fortunes as the “gangster studio” in this period by cranking out dozens and dozens of shoot-em-up crime stories. White Heat is actually one of the latest from what would be considered the gangster movie’s heydey, but it may be the greatest of them all in terms of acclaim and lasting Hollywood iconography. Jimmy Cagney of course plays the lead, as he did in so many other gangster pictures after being typecast as the iconic, fast-talking tough guy. By the time of White Heat though, Cagney was going on 50, trading a bit of his typical charismatic fire for a deeper character, not a charmer but a scheming psychopath undone by his weaknesses. The film heavily features the iconic Stateville Correctional Center, where Cagney works off his crimes and sinks only deeper into trouble, and in general the film features plenty of the seminal Chicago-area gangster feeling that films like Road to Perdition have continued to mine in recent years.
6. Henry: Portrait of a Serial Killer
Director: John McNaughton
Chicago has never looked more apocalyptic and hopeless than in Henry: Portrait of a Serial Killer, which stars a way, way pre-Walking Dead Michael Rooker as the titular serial killer (surprise!) based on Henry Lee Lucas. The Chicago of this film, much like New York City in the same time period, just looks like a dirty rat’s nest of a city, a warren for criminals that have long since cannibalized the corpse of the American Dream. Its ugly, alternatingly dirty and gaudy palette of drab urban decay and glaring neon lights highlight the worst of what every Illinois resident thinks about the Big City when they picture it in their mind. The characters of Henry, a film still shocking today in its depravity, are psychos, prostitutes and the great unwashed masses, the kinds of faces one might see on Chicago’s L-train in the early hours of the morning—and let there be no doubt, they’re the kind of faces you’d actively avoid eye contact with.
7. Adventures in Babysitting
Director: Chris Columbus
I seriously waffled on whether Adventures in Babysitting would belong on the list for issues of authenticity—the whole story revolves around Elizabeth Shue’s babysitter character adventuring through Chicago with the group of kids she needs to keep safe, but there’s a catch: Much of it was actually filmed in Toronto, Hollywood’s favorite “fill-in for any other large city” location. Still, it’s hard to deny Adventures in Babysitting in the end, both for being an ’80s family classic but especially for one of the climactic scenes, where the young girl Sara, pursued by criminals, ends up sliding down the slanted face of Chicago’s iconic Crain Communications Building, better known as the “diamond building” or the Smurfit-Stone Building. Such an intent focus on one of the best-known buildings on the Chicago skyline helps give it a local flavor that it might otherwise be lacking.
Director: Tim Story
“It began as just another day on the South Side of Chicago,” intones the trailer for Barbershop in its intro, and that’s what the film manages to capture fairly well—not the glitz and glamor of the Magnificent Mile and the city’s numerous tourist attractions, but the real heart and soul of one of its many South Side urban neighborhoods and the tight-knit community that exists there. The setting of the barber shop itself is uniquely perfect for film: So ubiquitous and identifiable to any city resident that it immediately achieves an easy familiarity. It was easy to see why (primarily black) audiences embraced the film in theaters, because the humor, particularly the conversational and pop culture observational humor of Ice Cube and Cedric the Entertainer, rings so true to life. The actual plot is a fairly relaxed, lazy affair about first trying to sell and then hang on to the ownership of the barbershop, but plot isn’t really important—rather, it’s a film that evokes and pays tribute to whole Chicago communities that are so often marginalized or never seen in a positive light on the big screen. It’s a film with a lot of heart that both acknowledges the challenges and the uplifting soul of its urban setting.
9. Wayne’s World
Director: Penelope Spheeris
Ever since the genesis of the duo on SNL, Wayne Campbell and Garth Algar were always proud broadcasters from “Cable 10 Public Access in Aurora, Illinois,” and those Midwestern sensibilities lie at the very heart of both the sketches and the two feature films. Wayne is exactly the sort of genial, goodhearted but fairly dim everyman slacker so often lampooned in other shows of the same period based in the Midwest (most notably MST3k). He still lives in the basement of his parents’ suburban home, the big fish in an extremely small pond of local broadcasting, without any real ambitions even to expand the scope of Wayne’s World. One might actually say his lack of vision or ambition is presented as a virtue: Wayne and Garth are just simple people, happy with what they have, where Rob Lowe’s antagonist character, Benjamin, is an upwardly mobile schemer. These are exactly the roles you expect to see characters play when set in the realistic, somewhat milquetoast setting of Illinois suburbia.
10. Drinking Buddies
Director: Joe Swanberg
In 2013, mumblecore auteur Joe Swanberg set his sights on a slightly larger budget, but still improvisational romantic comedy/drama, and the result was Drinking Buddies, a film set primarily between characters who work together at a Chicago craft brewery. It’s a tale about modern love and the entanglements of our relationships, and how we cling to them out of duty or responsibility rather than embracing what we truly want. It feels like a very intimate, urban story, one that would no doubt feel pretty darn familiar to Chicago’s apartment dwellers, perhaps living right down the hall from the person of their dreams, but unable to ever make it happen. Is it better to go on living there, knowing that you’ll at least get some degree of contact with the object of your affection? Or move away entirely, removing the signs of your failure from daily life? Drinking Buddies is about today’s current generation of older 20-somethings and younger 30-somethings as they painfully struggle to admit to themselves how they really feel about relationships and risk some parts of themselves they’ve never been willing to risk. And it even features the most disgusting and iconic Chicago liquor of them all, Jeppson’s Malort.