What makes Chicago such fertile ground for filmmaking?

The very difficult and continuing challenges of America—race, poverty, class—are explicit and powerfully on display here. There’s no place else, probably, where that is writ more large. But there’s also a spirit and pride that people have about this place. I look for people who are heroic in how they are trying to overcome. I find those people here all the time.

What were your first impressions of Chicago when you moved here in 1985?

I just remember the intensity. Harold Washington was mayor, and Council Wars were raging. I just thought, Wow, this place is really on edge. Because people were not mincing words over race and politics. I remember driving through the West Side and imagining, God, if we could get Hoop Dreams off the ground, I could be filming in these communities. That was exciting to me.

What did making Hoop Dreams [1994] teach you about the city?

I was also working on television commercials at the time. So I found myself around people and places where there was a lot of money, and then in my spare time I was doing this film with people who had no money. Chicago is a remarkable place with remarkable people; at the same time, it just rips your heart out. When I made The Interrupters [2011], the experience gave me a different understanding of the city’s communities. I certainly saw despair, but I also saw tremendous will, determination, and love.

Do you also see Life Itself [2014] as a film about Chicago?

It’s a love letter to Chicago through the life of Roger Ebert. What I loved about Roger’s story was that he came to Chicago and thought it was going to be a pit stop but never left. He loved this city, and he didn’t just love the skyline and the fine, fancy restaurants. He was really, truly a man of the people here.

Is this city still a source of inspiration for you?

Absolutely. What I’m intent on doing, maybe in the next couple of years, is a kind of portrait of Chicago. The city is at a crossroads on a lot of fronts. It wouldn’t just be a portrait of black Chicago or poor Chicago. I want it to be a truly mosaic portrait of this whole city. So, no, I’m not done telling Chicago stories.