In a moment that combines artistry, skill and a little bit of luck typical of a Steve James documentary, the best exemplification of the spirit of Chicago comes almost exactly at the halfway mark of “City So Real,” the “Hoop Dreams” director’s love letter to his hometown, with a woman at Daley’s Restaurant on the South Side acting as the film’s beating heart. The setting is rife with symbolism when the hundred-year old greasy spoon is one of the many family businesses of the Daleys, whose political dynasty in the mayor’s office ran for the better half of the 20th century, but it’s a homeless Black woman that best represents the state of things, proud and gregarious enough to sing “Noel” for customers as the Christmas season approaches with plans to volunteer for mayoral candidate Willie Wilson, but has to worry about where she’ll lay her head at night, seemingly as content as everyone else to chalk things up as being “the Chicago way.”
“Brokenness is a way to grow and learn,” she says, alluding to her precarious situation and she might as well be talking about what James and his team capture over the course of the four-part miniseries — or film, as the filmmaker insisted at its unveiling in full at the True/False Festival. After recently tackling the public school system in the Windy City with the 10-part “America to Me,” the filmmaker uses the opportunity of the 2019 mayoral election to illustrate what a unique metropolis it it is, for better or worse, while speaking to larger cultural and political realities. This being James, the traditional narrative tropes associated with a campaign quickly fall away when seen through his distinctly human lens, unfolding chronologically giving some sense of the race at hand, but rarely making it feel as if it’s a competition that will have winners and losers. Instead, it’s a far more nuanced look at an election cycle where some of the most riveting sequences happen at the usually quiet Board of Elections involving the minutiae of getting onto the ballot, with candidates sending surrogates or appearing themselves to contest the names on their petitions to qualify descends into all-out war at times.
James credits his collaborator Alex Kotlowitz on “The Interrrupters” for inspiring the film, which takes its title from the author’s 2012 survey of the city, “Never a City So Real,” but the director has kept returning to his hometown to look at its social fabric from different angles that it must be his own unmistakable institutional knowledge that informs every shot, a necessity when he hits the great majority, if not all, of Chicago’s 77 community areas, which are noted on a corner map each time his crew films in a new one. Every neighborhood has its own distinct personality, making the notion of any mayoral candidate capturing a majority of voters almost unthinkable, but still there’s no shortage of those who want to try after Rahm Emmanuel proved so unpopular he declined to seek a third term.
Nearly as unimaginable at this point in time is the city electing a Republican, though former superintendent of the Chicago PD Garry McCarthy and businessman Wilson (a slick scene-stealer) make a go of it, turning the campaign a battle between upstarts such as Chance the Rapper-backed Amara Enyia and tech entrepreneur Neal Sáles-Griffin and entrenched power such as former White House Chief of Staff Bill Daley and longtime Alderman Toni Preckwinkle. By now the nation should be familiar with the eventual victor Lori Lightfoot, a former president of the Chicago Police Board who can be seen hustling harder than anyone else for votes by knocking on doors and hitting up subway stations, but naturally James is as interested in the voters as much as the candidates, alleviating any need to rely on an outcome for intrigue. The film finds it instead everywhere from high-rises to corner pharmacies with residents responding to the issues of the campaign in casual conversations with a complex calculus of class and race that emerges organically.
The ongoing trial of the officer responsible for the murder of LaQuan McDonald and the proposed construction of a police training facility in the middle of a Black neighborhood on the South Shore, as well as the development of Lincoln Yards, a soulless mixed-use property aimed at attracting the wealthy to the riverfront at the expense of the working class, can easily bring emotions to the surface, but “City So Real” is constantly getting underneath to show how a deep sense of history is something to be proud of when being a Chicagoan has provided an identity that supersedes all others, yet remains an impediment when so much of government policy and the political establishment is tied to the past. By exposing the imperfections in the election process, the film needn’t delve into the futility of actually enacting meaningful reform, but given the times we’re in — and reportedly, James is currently at work on an addendum in the aftermath of the Black Lives Matter protests that overtook the nation following the murder of George Floyd — the passion to pursue public service and to vote is hopeful enough and with all its faults, “City So Real” shows Chicago in all its beauty.