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Here Are the 10 Best Chicago Documentaries

Life Itself, Steve James’s tribute to Roger Ebert, comes out on DVD February 17, a good excuse to catch up on other great Chicago documentaries.

In a moment of triumph from Hoop Dreams, Arthur Agee is carried off the court by his teammates.   Photos: (1, 4, 8, 10) Courtesy of Kartemquin Films; (3, 6, 9) Courtesy of Chicago Film Archives; (2) Courtesy of Nomadic Pictures; (5) Courtesy of Regressive Films; (7) Pentimenti Productions
A scene from ‘Hoop Dreams’

1. Hoop Dreams (1994)

For this alternately thrilling and heartbreaking film, Steve James spent five years following two inner-city boys who hoped to play pro basketball someday.

A scene from ‘Legacy’

2. Legacy (2000)

Tod Lending’s Oscar nominee tracks three generations of women living in the Henry Horner Homes as they cope with the murder of a 14-year-old relative.

A scene from ‘Rape’

3. Rape (1975)

Victims of sexual assault and harassment talk about their experiences in JoAnn Elam’s film, an important record of the hostile attitudes women faced in the 1970s.

A scene from ‘The Interrupters’

4. The Interrupters (2012)

Collaborating with author Alex Kotlowitz, Steve James trails the efforts of a persistent few trying to break the cycle of violence in their neighborhoods.

A scene from ‘You Weren’t There: A History of Chicago Punk 1977–1984’

5. You Weren’t There: A History of Chicago Punk 1977–1984 (2007)

Joe Losurdo and Christina Tillman immerse you in the noisy, energetic, and contentious underground scene.

A scene from ‘The Corner’

6. The Corner (1963)

This obscure black-and-white project by Robert Ford (a Northwestern student at the time) focuses on West Side members of the notorious street gang the Vice Lords.

A scene from ‘Hairy Who & the Chicago Imagists’

7. Hairy Who & the Chicago Imagists (2014)

Chicago’s celebrated group of subversive painters springs to life in Leslie Buchbinder’s vibrant film—a mix of animation, archival footage, and interviews.

A scene from ‘Inquiring Nuns’

8. Inquiring Nuns (1968)

Two Catholic sisters ask random passersby, “Are you happy?” in Gordon Quinn and Jerry Temaner’s delightful film that reflects the social unrest of the 1960s.

A scene from ‘8 Flags for 99 Cents’

9. 8 Flags for 99 Cents (1970)

With their superb foray into white middle-class anger over the Vietnam War, filmmakers Chuck Olin and Joel Katz debunk the notion that only hippies were peaceniks.

A scene from ‘Now We Live on Clifton’

10. Now We Live on Clifton (1974)

A series of interviews in this early project from Kartemquin Films captures the initial stages of gentrification in Lincoln Park, as yuppies displace blue-collar families.



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