Mayoral candidate Amara Enyia in City So Real.

James Bryce said that Chicago is “perhaps the most typically American place in America.” Filmmaker Steve James updated that: “What Chicago is struggling with, America is struggling with.” I spoke with James, a two-time Academy Award nominee for Hoop Dreams and America to Me, and his partner and producer Zak Piper, just before the world premiere of two of four one-hour episodes of the new documentary City So Real at the Sundance Film Festival in Park City in January produced by Participant Media and Kartemquin Films. All episodes (including an updated fifth bonus episode) are now streaming on Hulu.

“A mosaic of the city itself,” as James says, this honest and intimate series is a captivatingly broad profile of Chicago that James has wanted to do for years, an energized and passionate look at the real-life characters of this diverse and segregated city. Between what he calls “the most wide-open mayoral election in Chicago history,” and the “single most important trial in Chicago history” of Chicago cop Jason Van Dyke for the fatal shooting of Laquan McDonald, the city was dealing directly with its identity and its future.

The city of Chicago is a mosaic of neighborhoods, so naturally James’s approach is broad and patchwork. Spanning nearly every neighborhood in Chicago, with interviews from every walk of life, the first 15 minutes alone explore a myriad of subjects such as gentrification, development and who benefits from it, relationships between police and minority communities, who will lead us, how do we educate our kids, and activism. “These are universal themes America is dealing with,” James says. “Activism has taken on a force in the country which it hasn’t in a while, and Chicago is front and center in that movement.” Given the national spotlight on the city, James realized the time was right for this poignant portrait of Chicago. “Even though we’re the poster child for urban violence, we’re not even in the top ten per capita for urban violence,” James notes.

James takes a much different approach from his past work, such as The Interrupters or Life Itself—he casts a wider net, remaining open to whatever the filmmaking process presents, which allows for a vast variety of experiences that epitomize Chicago itself. While shooting past films, James says he was forced to cut interesting side characters, conversations, and events for time, but City So Real‘s five-hour running time allows him more space to improvise and let the story develop organically.

During a campaign event for Paul Vallas in Woodlawn, a woman approached the filmmakers asking to be in the film. “We find out she’s homeless,” James says, “she’s wearing a Willie Wilson pin, and she volunteers for him because it’s a place she can be.” Then in a wonderfully unexpected turn she says, “It’s [the holidays], ain’t no sense in being sad about nothing.” Reflecting on her life, she adds, “brokenness is a way to grow and learn.” She loves singing carols for people, “so we jump into that,” James says, his face lighting up, “it’s just a beautiful moment . . . those are the kinds of things we live for, when we get surprised in these wonderful ways.”

James and Piper intentionally did not want to make a traditional election film, embedding with a campaign or two and telling the story from the inside out. “We would be open to wherever the day would lead us, where the campaign would lead us, or what’s going on in Chicago would lead us,” James points out. This organic approach allowed the campaign and the city itself to dictate the direction and scope of the film. “We would have a plan in the morning . . . and we would just wing it the whole day,” Piper says.

James simplified his production, shooting most of the film himself along with his son, co-cinematographer Jackson James. They would race from one end of the city to the other, to capture in real time the reactions and responses from widely disparate neighborhoods. In one particularly fun scene, recounting the Chicago Bears loss to the Eagles during the playoffs, they shot the tailgating in the Soldier Field parking lot, raced to a south-side bar for the kickoff and first half, then hightailed it to the northwest side for the second half, showing three very different environments and capturing the unique spirit of each.

James approaches Chicago with empathy and honesty, neither attacking it nor writing a love letter to it. “I see things that distress me profoundly,” he says. “I also see tremendous inspiration. I see people who amaze me and surprise me and who care.” James captures all this in City So Real, the true pride of being a Chicagoan.   v