‘City So Real’: In-depth, epic documentary captures big stories and small in a splintered Chicago

It’s Christmastime in the city of Chicago. A homeless woman in a popular diner in Woodlawn on the South Side sings a lovely, a cappella version of “Noel,” to the delight of customers. We cut to the busy Ice Skating Ribbon at Maggie Daley Park, with a pop version of the same tune playing on the loudspeakers.

It’s election season in the city of Chicago. Lori Lightfoot is going door to door, trying to drum up support. Willie Wilson tries to get legendary Sun-Times City Hall reporter Fran Spielman to sing with him; she cheerfully declines. Bill Daley hosts a reception for supporters at a River North steakhouse. Amara Enyia holds a rally with a huge media turnout, thanks to the presence of supporters Chance the Rapper and Kanye West.

It’s a time of unrest in the city of Chicago. Protesters gather outside the courtroom where Jason van Dyke is on trial for shooting Laquan McDonald 16 times. We see marches against violence and systematic racism in Hyde Park, Bronzeville, the Loop, Wrigleyville, the Gold Coast — everywhere.

The overworked cliché about “two Chicagos” dissipates quickly in the five-part National Geographic docuseries “City So Real,” from the prolific and greatly skilled Steve James (“Hoop Dreams,” “The Interrupters,” “America to Me”).

James and his crew (his son Jackson served as cameraman and does a beautiful job) visit nearly every pocket of the city, from North Lawndale on the West Side to Woodlawn on the South Side to Lincoln Park to River North to Pilsen to many more, proving it’s more like there are 50 Chicagos. Maybe a hundred. All unique, complex and special neighborhoods, all gathered under one civic umbrella but in some ways never really connecting.

Chicago Story Film, LLC

“City So Real” feels like a sprawling, epic, Tom Wolfe nonfiction book caught on film, as it captures stories huge and small, showcases the astonishing beauty and the heartbreaking blight of Chicago and introduces a number of memorable real-life “characters,” in multiple storylines set against the big-picture backdrops of the 2019 mayoral election; the protests and calls for real change throughout the city; and the onset of the pandemic in the spring of 2020. Somehow, even the tedious process of the Chicago Board of Elections hearing challenges to voter signatures is engrossing, as representatives of more than a dozen candidates for mayor badger and challenge one another. Talk about the Chicago Way!

James conducts traditional interviews with a number of subjects — including a 2020 sit-down with Lightfoot filled with softball questions and painting her in a favorable light that might irk her detractors — but the most fascinating segments in “City So Real” are the fly-on-the-wall slices of Chicago life.

Chicago Story Film, LLC

We see two very different discussions about race in two very different South Side barbershops — a Black-owned salon and a spot with a predominantly white clientele. We attend a posh dinner party in the Gold Coast apartment of former Playboy Enterprises CEO Christie Hefner, attended mostly by wealthy and influential movers and shakers, including a former bank CEO who defends indicted Ald. Ed Burke and says he really doesn’t want to go back to the time when Harold Washington was mayor. We meet hardworking, classic Chicagoans such as Katie and Tim Tuten, owners of the Hideout in Bucktown, who are protesting the mega Lincoln Yards development in the neighborhood. We see Black fans of the Bears jamming to “Ain’t No Stopping Us Now” during a commercial break of the Bears-Eagles playoff game, and a white crowd watching that same game at the Windsor Tavern in Jefferson Park, where a sign on the wall says, “POLICE LIVES MATTER.” (They share a feeling of utter disbelief when Cody Parkey’s last-second field goal attempt double-doinks off the upright and the crossbar.)

Chicago Story Film, LLC

When “City So Real” played at Sundance last January, there were four episodes, ending with Lightfoot and Toni Preckwinkle emerging from the pack of candidates for a runoff that Lightfoot won in a landslide. The fifth episode kicks off a year after the election, with the pandemic starting to spread and Mayor Lightfoot telling Chicagoans: “Here’s the reality: You must stay home.”

We revisit some of the folks we met in earlier episodes; not surprisingly, the small businesspeople are already hurting. The breakout personality of Episode Five is Ald. Sue Sadlowski Garza (10th), who takes the filmmakers on a tour of her ward, pointing out the Wolf Lake area and saying, “You can hunt here, I mean, you can shoot s----.” When asked what you can hunt, she replies, “Ducks and … ducks.” Garza laments of her ward, “This is the forgotten part of the city … people [here] are always getting crap. We have nine landfills in our ward. Name another ward that even has one.” And she becomes visibly emotional when she talks about the unrest in the city.

Many of the images in the final episode are all too recent and familiar to Chicagoans. The bridges go up. A curfew is enacted. Restaurants re-open with outdoor, social distance seating. Protesters and police clash. Looters pillage stores and restaurants. Christopher Columbus statues are taken down. Some folks are wearing masks; others refuse to do so. Chicago is the American city, but in 2020, it’s like so many other American cities.

My favorite moment from “City So Real” takes place in an earlier episode, set during one of the coldest spells the city has ever known. As we see a montage of the city in all its stark, imposing and yet poetic wintry glory, we hear “On My Way to Heaven” by the Staple Singers. Like virtually every sequence in this series, it’s quintessentially Chicago.