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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.