The best Chicago movies (50–41)
The newest entry in our list didn’t make a huge impact in its 2016 limited release. Still, its South Side location filming and bevy of Chicago actors in the supporting cast entice, and the story—the first date between young Barack Obama (Patrick Sawyers) and Michelle Robinson (Tika Sumpter)—has to count, at this point, as a modern Chicago legend.
If you grew up in the suburbs of Chicago, you probably remember the watered-down, corn-fed personalities that were all too common in the classrooms of your public schools. Bad Teacher features a character that's just the opposite. Cameron Diaz plays a pot-smoking, booze-drinking, pill-taking suburban middle school teacher who takes the job only so she can save up for a boob job. She falsifies exam score, dry humps a spunky substitute (Justin Timberlake) and generally lives up to the movie's title.
Spike Lee’s contentious satirical musical pits the women of a South Side neighborhood, modeled after Englewood, against its men. Based on the ancient Greek comedy Lysistrata, the film follows what happens when women collectively stop having sex with men in an effort to curb gang violence and in-fighting that plague the neighborhood. Nick Cannon, Wesley Snipes, Jennifer Hudson, Angela Bassett and Samuel L. Jackson top a star-studded cast with plenty of scenery to chew.
Based on Will Kern's play Hellcab, a late-night cult favorite at Famous Door Theatre for a long stretch of the ’90s, this low-budget adaptation follows a tetchy cab driver (Paul Dillon) around the city as he picks up a raft of oddball fares on Christmas Eve. Shot at upwards of 40 locations around the city, the movie offers up dozens of juicy cameo roles for Chicago-connected actors, from higher-profile stars like Gillian Anderson, John Cusack, and Julianne Moore to such familiar local faces as, Tracy Letts, Ora Jones, Mary Ann Thebus, Shanesia Davis, Moira Harris and a 22-year-old Michael Shannon, in a role credited as "Crack Head."
Second City alum Jeff Garlin (Curb Your Enthusiasm) plays a sad-sack Second City performer who sees potential to turn around his life after meeting quirky ice-cream shop worker Sarah Silverman. The sole feature by writer-director Garlin, this passion project was filmed on location in the city and is replete with Chicago pals like Bonnie Hunt, Amy Sedaris, David Pasquesi and Tim Kazurinsky; original Second City ensemble member Mina Kolb plays Garlin's mother.
Writer-director Bonnie Hunt's off-kilter romantic comedy, in which widower David Duchovny falls in love with the woman, played by Minnie Driver, who was the recipient of his late wife's donated heart, similarly shows off Hunt's native Chicago. Old Town's Twin Anchors stands in for the Irish/Italian restaurant where Driver's Grace waits tables.
The Cubs were baseball's most lovable losers for the better part of a century, so it makes sense that this 1993 flick would bring the North Siders a savior in the form of a 12-year-old boy. The film opens with little leaguer Henry Rowengartner (Thomas Ian Nicholas) breaking his arm while trying to catch a fly ball. Upon getting his cast off, he discovers that he now throws an incredibly fast pitch. The Cubs uncover his talent during a game at Wrigley Field so, naturally, he leads the team to a World Series championship—child labor laws be damned!
Sweet, innocent Julia Stiles charmed us with her acting and her dance moves—we get to see her do both ballet and hip-hop—when we fell in love alongside her and Sean Patrick Thomas’s character in this 2001 chick flick about an interracial relationship and small-town drama. But what we love seeing perhaps even more are shots of our very own CTA rail system, the bright and beautiful Loop and the Chicago Academy of the Arts in West Town.
Michael Mann's take on Chicago's gangster era starred Johnny Depp as John Dillinger, Channing Tatum as Pretty Boy Floyd and Christian Bale as FBI agent Melvin Purvis. But the real star, arguably, is the film's gorgeous cinematography, restoring locations like Union Station and the Biograph Theater to their gritty period glory.
The best Chicago movies (40–31)
Adapted from David Mamet's 1974 play Sexual Perversity in Chicago, this drama about a twentysomething couple (Demi Moore and Rob Lowe) and their romance-cynical best friends (Elizabeth Perkins and Jim Belushi) departed significantly from its source material but added some authentic Chicago touches. The characters play 16-inch softball in Grant Park and hang out in the exact Lincoln Park and Division Street bars where you can find their modern-day counterparts now.
An ultra-charming 16-year-old River Phoenix starred as a teenage lothario in this coming-of-age story set in 1962 Evanston. With shooting locations in both Chicago and around the North Shore, writer-director William Richert (adapting his own novel) aptly captures the contrast between the city and the suburbs.
Ah, Julia Roberts. Watch as she dashes to and from O'Hare, the home of the White Sox, the El and, of course, Fourth Presbyterian Church on East Chestnut Street. The classic 1997 tearjerker never lets you down when you need a good cry, as Roberts’ character realizes, perhaps too late, that she's in love with her longtime pal (Dermot Mulroney) who is about to tie the knot.
Second City Toronto alum John Candy plays an unemployed Chicago city slacker who gets roped into babysitting his nieces and nephew in the suburbs after the father of his brother’s wife suffers a heart attack. He wins the hearts of the trio of siblings with charming antics, like making giant birthday pancakes with a shovel, showing the kids his favorite bowling alley and driving around a beater of a car that backfires through the streets.
Sure, it's a little hard to buy Sandra Bullock as a CTA station attendant (remember tokens?). But this unconventional rom-com—in which Sandy is mistakenly identified as Peter Gallagher's fiancée after saving him from a fall on the tracks but falls in love with his brother, Bill Pullman, while Gallagher is in a coma—is easily the most romantic cinematic representation of the El.
Few films offer more gorgeously composed shots of Chicago than the those contained in this Depression-era mobster tale, adapted from a graphic novel by Max Allen Collins. Road to Perdition follows a mob enforcer played by Tom Hanks, whose family unwittingly becomes embroiled in his violent line of work. Joined by his son, Hanks’s character sets out on a vengeful mission, visiting locations in the Loop and the Pullman Historic District along the way.
Keanu Reeves plays Conor O'Neil, a gambling addict who's down on his luck, in this 2001 flick about redemption. In an effort to dig himself out of a crippling debt, O'Neil takes a loan from a friend with the condition that he coaches a little league baseball team from Chicago's now-demolished ABLA Homes. In true cinematic fashion, the 11-year-olds end up teaching him all about teamwork, work ethic and believing in yourself. Hardball is filled with references to the city that are still relevant today, perhaps the best of which is when he asks a schoolteacher played by Diane Lane on a date to "a bar at Clark and Addison. It's called Sluggers."
The best Chicago movies (30–21)
Robert Redford's directorial debut, filmed largely on the North Shore, follows a family reeling from the accidental death of a son. Timothy Hutton won an Oscar as tormented teen Conrad, blaming himself for his brother's death; Mary Tyler Moore got a nomination as his ice-cold mother, who blames him too. The subject material may be difficult to identify with, but the scenery of suburban Lake Forest is easily recognizable.
Former Columbia College Chicago professor Audrey Niffenegger's best-selling novel about a time-displaced man and his wife was adapted into this Rachel McAdams and Eric Bana helmed sci-fi/romance hybrid. It was largely shot in Canada (ugh), but the Newberry Library, where Bana's character works as a librarian, figures prominently into the plot.
The famous movie with six kids stuck in their school’s library for detention takes place in the city’s suburbs—the library is modeled after the one belonging to Maine North High School, which closed prior to the filming. The school makes an appearance in another famous film, Ferris Bueller’s Day Off. As for that final fist pump, well, that was filmed on the school’s football field too.
Filmed almost entirely in Canada, complete with CGI El trains (booooo), the Oscar-winning film adaptation of John Kander and Fred Ebb's 1975 musical—based on former Chicago Tribune reporter Maurine Dallas Watkins's 1926 satirical play drawn from two real-life "merry murderess" cases she'd covered—nonetheless captures real and amusing truths about this city's ever-loving corruptibility.
If you want an idea of the effect that gun violence has on some of Chicago's most vulnerable communities, The Interrupters is a great place to start. Directed by Steve James (who was behind the 1994 Chicago-based documentary Hoop Dreams), the documentary follows a group of community leaders who work to disrupt violence in the city through on-the-ground action. It's easy to read the seemingly endless stream of news headlines about Chicago homicides and write entire swaths of the city off as violent—The Interrupters portrays a group of people who, with a clear shortage of resources, manage to have a positive impact.
Chris Columbus's kid-caper film about a babysitter (Elisabeth Shue) who is forced to drag her suburban charges into the city to rescue a friend in trouble was largely filmed in Toronto, with some location shoots involving the CTA. But the movie hilariously and accurately captures the suburban fear of "downtown," and it made the Smurfit-Stone (now Crain's) building famous.
This earnest romance from writer-director Theodore Witcher features Larenz Tate and Nia Long as a young Chicago couple testing the seriousness of their on-again off-again relationship. Eschewing the violence and drugs that populated most African-American films of the era, this touching, Chicago-based movie took home the Audience Award at the Sundance Film Festival.
Sidney Poitier, Ruby Dee and most of the original cast of Lorraine Hansberry's play, which had a run at Chicago's Blackstone Theatre ahead of its Broadway bow in 1959, returned to the city to reprise their roles for the 1961 film adaptation. Hansberry's story of an African-American family hoping to move into an unwelcoming white neighborhood, informed by her own family's experience, is among the most indelible depictions of the black experience in Chicago.
The best Chicago movies (20–11)
A quarter-century after The Hustler, Paul Newman reprised his role as pool shark "Fast Eddie" Felson, this time playing mentor to Tom Cruise's small-time shooter. The Martin Scorsese film used local venues including FitzGerald's and the Gingerman Tavern to stand in for pool halls around the country. Perhaps the most appropriate recasting of a locale is the Navy Pier ballroom’s turn as a boardwalk hotel in Atlantic City, where the Nine-ball Classic Tournament is held.
Tina Fey's first feature film was this inventive and instantly iconic teen comedy, set at a thinly veiled version of Evanston Township High School and partially informed by Fey's time working a day job in Evanston while studying at Second City. It's too bad Lindsay Lohan didn't seem to learn anything from her own character's journey.
John Cassellis (Robert Forster) is a hardened TV news cameraman who manages to keep his distance while he captures daring footage of a nation in the throes of violent change. He maintains this professional detachment when he covers the social unrest in Chicago surrounding the 1968 Democratic National Convention. But, when he discovers that the TV network has been quietly cooperating with the FBI, the enraged Cassellis realizes that he too must join the fight against the establishment.
Nia Vardalos’s comedic story about how she (in real life) met her non-Greek husband, Ian, takes place in Chicago (although it was mostly filmed in Toronto). Vardalos is a Second City alum and has family in the city, which is why she chose to set the film in Chicago. The movie has nods to Greektown—in the movie, her family owns a restaurant, Dancing Zorba’s, in the neighborhood, where she works before getting a job at a travel agency, where her fateful meet-cute occurs.
A three-hour documentary about basketball is probably not most people's idea of a night out, but this one rewards the effort. Steve James' essential inner-city epic chronicles the lives of two young black men growing up in a Chicago housing project. At 14, basketball prodigies Arthur Agee and William Gates win scholarships to a suburban high school, St Joseph's. Then their fortunes diverge. William looks set to follow in the footsteps of St Joe's favourite son, all-star Isiah Thomas. Arthur doesn't make the cut. Over the next four years, however, the boys' lives are to intersect more than once, and in unexpected ways. James and his collaborators shot more than 250 hours of footage, and the cumulative emotional power is simply devastating.
John Sayles's retelling of the 1919 "Black Sox" scandal, in which eight Chicago White Sox players accepted payments from gamblers to intentionally throw the World Series, features an impressive cast including John Cusack as Buck Weaver and D.B. Sweeney as Shoeless Joe Jackson. Just don’t go into the movie expecting any familiar South Side ballpark scenery—Indianapolis's old Bush Stadium stood in for Comiskey Park.
It's hard to forget that Vince Vaughn is from Chicago—he seems to work in a reference to the city in pretty much every movie he's in. In The Break-Up he portrays an obnoxious owner of a Chicago-based (naturally) tour guide company who treats his live-in girlfriend (Jennifer Aniston) like a piece of dirt and is confused as to why she breaks up with him. They share a lovely downtown condo that neither of them can afford on their own, and the pair enter a battle of wits to see who will move out first. By the end of the film, Vaughn's character evolves from a homophobic, chauvinistic dickhole into a sensitive, self-aware man.
Public access television star Wayne Campbell (Mike Myers) hails from Aurora, Illinois and Wayne’s World was largely shot in L.A., but the movie’s opening scene betrays its Chicago setting. As Queen’s “Bohemian Rhapsody” blares from the Mirthmobile, establishing shots show the protagonist’s car whizzing down Milwaukee Avenue in Logan Square. It makes sense that suburbanites Wayne and Garth would spend their time tooling around Chicago (with the occasional excursion to Milwaukee for an Alice Cooper concert)—after all, it’s the Midwest’s most excellent city.
Kurt Russell and William Baldwin are second-generation Chicago firefighters investigating a series of arsons in Ron Howard's melodrama of corruption and pyrotechnics, which also features J.T. Walsh as a bribe-taking alderman (gosh, we'd never suspect such shenanigans of the real-life City Council). Filmed entirely on location in the city, the movie was nominated for three Oscars for sound and visual effects.
A silently professional night-time jewel robbery, reduced to near-abstract essentials and paced by a Tangerine Dream score, sets the electric tone for Mann's fine follow-up to The Jericho Mile: A philosophical thriller filled with modernist cool. James Caan plays the thief, contradictorily building and risking a future mapped out as meticulously as any of his lucrative hi-tech jobs; testing his emotional and criminal independence to the limits; eventually recognizing that he's either exercising or exorcising a death wish. Thief also marks the screen debut of real-life Chicago cop-turned-actor Dennis Farina.
The best Chicago movies (10–1)
Brian De Palma's 1987 take on the dueling forces of Al Capone (Robert DeNiro) and Eliot Ness (Kevin Costner) has a screenplay by Chicago scribe David Mamet; the creative team's vision is full of violence and style—witness the famous scene in which the pair turn a Union Station shootout into an homage to Eisenstein's Battleship Potemkin; for nearly two and a half minutes all you hear in the soundtrack are gunshots, Ennio Morricone's urgent score, and the sound of a baby carriage's wheels speeding down a staircase.
Chicago newspapermen Ben Hecht and Charles MacArthur's 1928 play The Front Page (which has had multiple screen adaptations under its own name), set in the press room of the city's Criminal Courts Building on the eve of an execution, both satirized and celebrated the era when Chicago had more than a half-dozen dailies competing for the most sensational (and maybe cynical) scoops. But it was director Howard Hawks's own screwball notion that makes this 1940 version even better: He swapped the gender of ace reporter Hildy Johnson, turning Hildebrand into Hildegard and making her the ex-wife of editor Walter Burns, thus giving their love-hate sparring a layer of romance. Stars Rosalind Russell and Cary Grant go at the script's rapid-fire wisecracks like wildfire.
Before going on to serve as a producer on the Barbershop series and Roll Bounce, George Tillman Jr. wrote and directed this small but lovely semi-autobiographical feature about three generations of a black Chicago family whose plot is propelled by their weekly gatherings for matriarch Mama Joe's Sunday soul food dinners. Soul Food stars Chicago actress Irma P. Hall as Mama Joe and Vanessa Williams, Vivica A. Fox and Nia Long as her three daughters. Hall reprised her role in a TV series adaptation that ran for five seasons on Showtime; the Tribune reported in 2015 that Tillman plans a sequel to the movie. Tillman, a Columbia College Chicago alum, has said he was inspired to make films after seeing Cooley High.
Penny Marshall's endlessly quotable look back at the wartime rise of women's professional baseball may focus largely on the Peaches of Rockford, Illinois, but its Chicago ties run deep. Geena Davis, Lori Petty and the rest of the girls go through tryouts at the Cubs' park (here called Harvey Field, with Garry Marshall playing a fictionalized version of league founder Philip K. Wrigley named Walter Harvey) and team manager Jimmy Dugan (Tom Hanks) a former Cubs slugger. Chicago filming locations included Wrigley Field as well as, once again, FitzGerald's, playing the dance hall.
Often described as a "black American Graffiti," Cooley High looked back with nostalgia on the early ’60s at the real-life Old Town high school that was largely fed by the Cabrini-Green housing project. A seminal African-American coming-of-age movie and a touchstone for a generation (or more) of Chicago kids, it was also the loose basis for the late-’70s TV sitcom What's Happening!!
John Cusack transferred the action of Nick Hornby's novel, about a man-child record store owner whose rock-snob music knowledge is no help in saving his failing relationship, from London to Chicago. With screenwriting partners D.V. DeVincentis and Steve Pink (like Cusack, Chicago-area natives), Cusack set up protagonist Rob Gordon's shop in a storefront at Milwaukee Avenue and Honore Street, next door to Nick's Beer Garden and down the block from Reckless Records at the height of Wicker Park's boho moment. There are references to local record labels Wax Trax!, Touch and Go and Drag City, authentic gig posters from Chicago venues like Schubas, and scenes shot at Double Door, Green Mill and Lounge Ax (RIP). High Fidelity makes it easy to believe that Rob and his friends were an authentic part of Chicago's ’90s music scene, without hitting you over the head with landmarks recognizable to non-locals. That's why this pic about an obsessive maker of top-five lists tops ours.