15 Essential Chicago Movies
Sweet Home Chicago
Three decades ago, Brian De Palma’s The Untouchables hit theaters. Kevin Costner stars as Eliot Ness, the U.S. Treasury agent who took down Al Capone (Robert De Niro) with a small team that earned the film’s title as its nickname. It’s an episode in American history that makes for a great movie — in part because it took place in a city that makes for great cinema. From gangsters and gunfights to baseball and the blues, check out these 15 movies that capture the essence of Chicago, ahead.
The Untouchables (1987)
Al Capone has been the subject of many movies, but Brian De Palma’s crime drama, from a script by David Mamet, is the best depiction of Chicago’s most infamous episode. Sean Connery won his only Oscar for playing Jimmy Malone, the experienced cop who helps Kevin Costner’s naïve Eliot Ness navigate the city's ruthlessness and rampant corruption to put Robert De Niro's Capone behind bars. “He pulls a knife, you pull a gun,” Malone tells Ness. “He sends one of yours in the hospital, you send one of his to the morgue. That’s the Chicago way.”
Rob Marshall’s glitzy film adaptation of the Bob Fosse musical Chicago is so entrenched in the mythology of its setting, it shares the city’s name. Leading ladies Roxie Hart (Renée Zellweger) and Velma Kelly (Catherine Zeta-Jones, who won one of the film’s six Oscars) operate under a highly questionable moral code that could only fly in this hyper-stylized, Prohibition-era Chi-Town: These two spotlight-hungry showgirls are willing to sacrifice anything — including a handful of other people’s lives — to be famous. But what’s a little bit of blood spilled if it’s all in the name of booze, sex, and all that jazz?
The Blues Brothers (1980)
“We’re on a mission from God,” Jake (John Belushi) and Elwood (Dan Aykroyd) Blues tell everyone they meet (and they meet everyone, from James Brown to Aretha Franklin to Ray Charles) as they embark on a truly sacred quest: Getting their band back together. Throughout John Landis’ rollicking crime comedy, Jake and Elwood will overcome any obstacle, including a series of wildly destructive car chases and Carrie Fisher with a flamethrower, to reassemble the Blues Brothers Band and put on a truly great show — which, mercifully, they do. And their big showstopping number? “Sweet Home Chicago.”
Five decades before Brian De Palma relocated Scarface to Miami and then made his own Chicago gangster drama with The Untouchables, Howard Hawks directed the classic that made both of those films possible. Paul Muni stars as Tony Camonte, a gangster in 1920s Chicago, clearly modeled after Capone. Don’t be fooled by its early code-era date, this Scarface is just as brutal as any other gangster flick — if a little more subtle. Just remember: X always marks the spot.
Spike Lee might be better known for his New York movies, but his recent musical satire Chi-Raq is all Chicago. Named for the city’s violent Southside in which it takes place, this topical Spike Lee joint takes its plot from Aristophanes’ Lysistrata, in which the women of Greece withhold sex from their partners in protest of the Peloponnesian War. Lee’s Lysistrata (Teyonah Parris) organizes the women of the Southside to do the same in an effort to end the neighborhood’s rampant gang violence — but America’s gun obsession and toxic masculinity will take more than forced abstinence to overcome.
Drinking Buddies (2013)
Among all these slick and stylish crime and music flicks, here’s something completely different! Joe Swanberg’s mumblecore comedy-drama stars Olivia Wilde and Jake Johnson as co-workers at a Chicago craft brewery who struggle to ignore the obvious sexual tension between them, despite both already having relationships. The film’s understated, improvised style has nothing in common with the flash of some of the more heavily imagined cinematic incarnations of the Windy City, but Drinking Buddies authentically captures the city’s hip, contemporary drinking culture.
Ferris Bueller’s Day Off (1986)
John Hughes drew from his experiences growing up in the Chicago suburbs for all of his now-iconic high school movies — but Ferris Bueller’s Day Off was his true love letter to the Windy City. When Ferris Bueller (Matthew Broderick) plays hooky for one day, he makes the most of it, and sees as much of Chicago as possible, hitting the Sears Tower, the Art Institute of Chicago, and Wrigley Field.
Hoop Dreams (1994)
Legendary Chicago film critic Roger Ebert was an early champion of Steve James’ indie Hoop Dreams, which Ebert called “one of the great moviegoing experiences of my lifetime.” A Sundance breakout, the documentary follows two inner city Chicago teenagers, both talented athletes, who dream of playing for the NBA. The moving film, which chronicles six years of the boys’ lives, depicts the determined boys’ hoop dreams in the context of the poor, black Chicago neighborhood they come from. James would go on to make the Chicago docs The Interrupters and Life Itself, about Ebert.
Eight Men Out (1988)
If you’re looking for a Cubs movie, there’s 1993’s lighthearted Rookie of the Year; the best Chicago baseball movie, however, has to be John Sayles’ dramatization of the 1919 Black Sox scandal, in which eight of the Chicago White Sox (played here by John Cusack, David Strathairn, and Charlie Sheen, among others) struck a deal with gamblers to throw the World Series. Say it ain’t so, Joe!
Southside With You (2016)
Richard Tanne’s more recent addition to the Chi-Town movie canon focuses on a pair of Chicagoans who have become, in the past decade, two of the most beloved and influential cultural figures in America: Barack and Michelle Obama. The Sundance breakout puts the spotlight on the former POTUS and FLOTUS — years before they took on those titles — for one night, dramatizing their first date back in 1989. Parker Sawyers and Tika Sumpter star as Barack and Michelle in the well-reviewed drama.
Medium Cool (1969)
Legendary cinematographer Haskell Wexler made his narrative writing and directing debut with this New Hollywood classic, which blends documentary-style footage with fictional scripted content. Wexler captured the 1968 Democratic National Convention in Chicago, weaving a narrative about a TV news cameraman character into the political event, which took place at a particularly fraught moment and resulted in protests. Forget “medium,” Wexler’s film is very, very cool.
High Fidelity (2000)
Devoted Chicagoan John Cusack shows up in three of the movies on this list, but High Fidelity is the one that truly belongs to him. Cusack plays Rob, a record store owner who, with his fellow music snob friends, constantly makes top five lists — including, over the course of the movie, his own top five worst breakups. Stephen Frears’ film transplants the Nick Hornby novel on which it is based from London to Chicago, and shines a light on the city’s alternative music scene.
Soul Food (1997)
Before he went on to produce the Barbershop films, George Tillman, Jr. wrote and directed this comedy-drama, which was later developed into a Showtime series that ran for five seasons. Inspired by Tillman, Jr.’s own family, Soul Food focuses on a large Chicago family that gathers every Sunday night to eat the title cuisine. But when the family matriarch is hospitalized, the tensions build between her three daughters and the family starts to fall apart.
A Raisin in the Sun (1961)
Daniel Petrie’s adaptation of Chicago native Lorraine Hansberry’s 1959 play — which the city’s own Tribune identified as “the greatest Chicago play” that “ripples with the complexities of all that is Chicago” — is a piercing evocation of a time, place, and community. Bringing back the original Broadway cast, including Sidney Poitier as Walter Lee Younger and Ruby Dee as his wife Ruth, the film follows the Younger family as they struggle to reach a better life away from Chicago’s East Side, and looks with clear eyes at how race and class shapes the family’s experience.
Adventures in Babysitting (1987)
Chris Columbus made his directorial debut with Adventures in Babysitting, a comedy about a babysitter (Elisabeth Shue) having an adventure (imagine that!) with her young charges all over the city. The film doesn’t break any new ground stylistically or narratively, certainly, but cleverly uses the identity of its setting to flesh out its formula skeleton. In what other city in America could a babysitter get out of a sticky situation by singing the “Babysitting Blues”?