Everyone is a critic, particularly when it comes to movies, and nowhere is that more true than in Chicago—after all, a television show with two guys arguing about films started here more than three decades ago and went on to become part of the national Zeitgeist.
So we are weighing in with our picks for the 40 greatest Chicago movies of all time. To keep the list manageable and to the point, we classify a Chicago movie as one where at least part of the picture was actually shot in town. That definition regrettably leaves out a bundle of favorites—Scarface, The Front Page, His Girl Friday, and even Chicago—that were set in the city but filmed elsewhere, usually Hollywood or Toronto. In selecting our 40, we sifted through hundreds of candidates—reeling back through our collective memories and hitting our Netflix accounts—to choose those that we thought captured a piece of Chicago in some iconic, evocative, or magical way. As always, you are free to disagree and tell us.
40. The Hunter (1980)
Steve McQueen’s last film is a sad mess, but the spectacular chase scene, including a car driving off Marina Towers, stands the test of time.
39. The Fury (1978)
A true guilty pleasure, as kids with occult powers go to a special Lincoln Park school and fight off a government plot.
38. Cooley High (1975)
A rollicking African American version of American Graffiti, loosely based on the high school, Cooley Vocational, that served the Cabrini-Green projects.
37. My Best Friend’s Wedding (1997)
This romantic comedy, with Julia Roberts pursuing love at a White Sox game and on the North Shore, hits all the bases.
36. Continental Divide (1981)
The Roykoesque reporter John Belushi brushes too close to corruption and bolts town, so only half the movie is set in Chicago, but that includes great shots of the since-demolished Sun-Times newsroom.
35. Candyman (1992)
Just when you thought gentrification was bad: This slasher movie tracks an urban legend through the UIC campus and various local public housing projects.
34. Sixteen Candles (1984)
John Hughes’s first movie about middle-class high-school kids remains one of his best and launched Molly Ringwald to teen stardom.
33. The Untouchables (1987)
Prohibition, gangsters, crimebusters, and the city itself never looked more smashing than in this Brian De Palma epic.
32. When Harry Met Sally (1989)
Their episodic journey begins in Hyde Park, then takes a wrong turn on Lake Shore Drive on the way to romance and NYC.
31. Backdraft (1991)
Dazzling special effects and a small role by Robert De Niro spark the plot about two antagonistic firefighter brothers and a serial arsonist.
30. Mercury Rising (1998)
Dark, shadowy action thriller shows impressive murk and suspense as Bruce Willis protects an autistic kid who can decipher government codes.
29. Only the Lonely (1991)
It’s the best movie ever made by John Candy, who plays a cop forced to choose between his mother and his girlfriend. Plus, great shots of Wrigleyville.
28. While You Were Sleeping (1995) This little sleeper of a romantic comedy enshrined Sandra Bullock, playing a lovelorn CTA fare-taker, as the adorable girl next door.
27. North by Northwest (1959)
Hitchcock’s masterpiece thriller has Cary Grant running for his life, including pivotal scenes at the LaSalle Street Station and the Ambassador East hotel.
26. Nothing in Common (1986)
Garry Marshall’s comedy about an estranged father and son made Tom Hanks a star and showcased Jackie Gleason’s final performance.
25. Soul Food (1997)
This enjoyable portrait of a matriarchal-centered middle-class African American family on the South Side was a long time coming.
24. About Last Night (1986)
Underrated romantic drama based on a David Mamet play has racy bedroom scenes between Demi Moore and Rob Lowe and a star turn by Jim Belushi.
23. Home Alone (1990)
If you can’t laugh at this family classic in which a left-behind kid outsmarts bungling burglars, you need an antidepressant.
22. Ordinary People (1980)
Cosseted life in Lake Forest—representing the American norm of happiness—can’t prevent a tragedy and the subsequent unraveling of a family. This gloomfest, directed by Robert Redford, is the only movie on our list to win a Best Picture Oscar.
21. His New Job (1915)
Made when Chicago was a film capital, before the weather drove the biz to California, the silent short stars Charlie Chaplin as a handyman who is pressed into acting.
20. Primal Fear (1996)
Someone has killed Chicago’s archbishop: Richard Gere defends Edward Norton, taking his first major movie role, in this suspenseful and, at times, tricky drama.
19. Thief (1981)
The director Michael Mann’s debut film is an atmospheric heist, including scenes at the Green Mill and a first big-screen appearance by Jim Belushi.
18. Road to Perdition (2002)
Visually stunning pictures tell the story of 1930s Chicago gangsters, with bleak weather mirroring the characters’ hearts.
17. Stir of Echoes (1999)
Not even six degrees separate Kevin Bacon from the intense paranormal creepiness in his seemingly normal working-class neighborhood.
16. I Am Trying to Break Your Heart (2002)
Not great storytelling, but the grainy band-at-work documentary follows Wilco through the recording of their pivotal album Yankee Hotel Foxtrot.
15. Public Enemies (2009)
Michael Mann’s expert use of 1930s locations captures the tarnished-gilt spirit of the Depression, while Johnny Depp humanizes Dillinger.
14. The Company (2003)
Brilliantly unexpected direction by Robert Altman makes this ensemble movie about the Joffrey Ballet feel like a documentary.
13. The Fugitive (1993)
One of the top catch-him-if-you-can films, with the falsely accused Harrison Ford being chased all over Chicago—including through Cook County Hospital and a St. Patrick’s Day parade.
12. Dislocation (2005)
Gritty documentary follows three local families during the demolition of their public housing project and their move to a strange new world.
11. The Blues Brothers (1980)
Their kind of town: The homeboy John Belushi, along with Dan Aykroyd, established Chicago as a raucously blues-singing, car-crashing, soul-swinging place.
10. Barbershop (2002)
What we talk about when we talk about life: An ensemble cast offers a window into African American culture via a South Side institution.
9. The Color of Money (1986)
Martin Scorsese casts the city’s West and South Side neighborhoods as supporting characters in a saga about a cagey, aging pool hustler (Paul Newman) and his protégé (Tom Cruise).
8. The Dark Knight (2008)
Holy cityscape! A spectacular last performance by Heath Ledger; plus 34 city locations, including the legendary bar Twin Anchors, are cast as Batman’s Gotham City.
7. Risky Business (1983)
What happens when the Home Alone-type kid grows up to be enterprising teenager Tom Cruise, including a sparky sex scene on the el.
6. Ferris Bueller’s Day Off (1986)
John Hughes wrote and directed a classic love letter to Chicago and to the kid in all of us who just wants some time to goof off.
5. Medium Cool (1969)
Melding cinéma vérité and fiction, the director Haskell Wexler captured the explosive mood of the summer of 1968, including footage of the Democratic convention riots.
4. Call Northside 777 (1948)
The first major Hollywood movie shot in Chicago, this film-noirish classic stars James Stewart as a skeptical reporter who ends up establishing the innocence of a wrongly convicted murderer.
3. Mickey One (1965)
French New Wave meets Nelson Algren when Warren Beatty and the director Arthur Penn, pre-Bonnie and Clyde, team up for a paranoid-man-on-the-run tale.
2. Hoop Dreams (1994)
Amazing documentary gives an intimate four-year look at two Chicago inner-city high-school athletes, their dreams, and those who exploit them.
1. High Fidelity (2000)
The British writer Nick Hornby’s novel was re-homed here, where the audiophile John Cusack goes on a quest to understand women. Does the music make this man or keep him from growing up? It’s a rich, textured movie that—like your favorite LP—only gets better with time. It defines Chicago as a city of doers, dreamers, and slackers—a real place for real lives.
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