Steve James’ latest masterpiece—and despite his creative modesty, the man has many, from “Hoop Dreams” to “The Interrupters” and other interrogations of America and what we expect from her—takes a massive subject and breaks it down into fractal pieces. Those discrete bits, made up not so much from Subjects and Themes but from the people who his camera frames in a quiet kind of curiosity, are then assembled together into “City So Real,” an expansive five-part portrait of Chicago tussling with its purpose, identity, and future in the new millennium. It’s a noble, heartfelt, and eye-opening look at the American city, matching the scope of Frederick Wiseman’s recent scoping of a similarly fractious Boston in “City Hall,” but giving it more of a warmly human pulse.

Ostensibly, the skeleton holding this thing up is the mayoral election of 2019. That was the year Barack Obama’s one-time consigliere, Rahm Emanuel, was finishing up his turn as the city’s version of a would-be Michael Bloomberg-esque technocrat. As James shows in the first episode, the start of campaigning in 2018 found the nation’s third-largest city reeling from a flurry of hits. Without a signature industry (Wall Street for New York, Silicon Valley for San Francisco, oil for Houston) to prop up finances with a reliable gusher of tax revenue, Chicago was facing the problems of many older industrial cities of the East and northern Midwest: slumping revenues from a dwindling population and an uncertain economic future. On top of that, the city was suffering from a steadily spiking crime wave and the contentious trial of a city police officer charged with second-degree murder for fatally shooting 17-year-old Laquan McDonald four years earlier. With that as a backdrop, some 14 candidates (give or take) decided they wanted to duke it out over who could best solve the city’s problems.

On the skeleton of that mayoral contest, which James uses as the main through-line for each of his episodes, the series grafts a series of miniature portraits that together serve as a pointillist rendering of a city too often summed up in limiting cliches. James sets up each of these disparate segments with a map that shows the location, both illustrating the truth of the line about Chicago being a “city of neighborhoods” and establishing the city’s fairly balkanized nature. He cycles from Black working-class locales like a homey century-old diner in Woodlawn to a pharmacy in North Lawndale, pivoting to the gentrifying Mexican enclave of Pilsen and a Bridgeport barbershop whose clientele appears entirely made up of retired White cops who have strong and unsurprising opinions about crime and race.

Even though, in the great Midwestern tradition, race is rarely brought up directly, it is a constant in the background. Even in a segment that is primarily about the city coming together for what looks initially like a big blowout win by the Chicago Bears, James cannot help but cut between two different bars showing the games: one uniformly Black and the other seemingly exclusively White.  There are other fractures in the city, too, between the city’s power center and its often forgotten far-flung neighborhoods that James visits (this is not a movie that spends much time trawling the familiar tourist-thronged backdrops of Grant Park, the Loop, and the Magnificent Mile); between the monied real estate interests pushing a gargantuan yuppie development and the scrappy Jane Jacobs-quoting anti-gentrifiers trying to push them back; and all those people running for mayor.

The candidates are a grab-bag of types, most of whom it is difficult to envision in the office. One of the frontrunners, Toni Preckwinkle, is a multi-term alderman and something of a Cook County lifer who has grabbed up a host of endorsements by calling in chits but has difficulty mustering answers without a cheatsheet to read from. Willie Wilson, an accomplished businessman with a somewhat daftly disconnected demeanor, does not seem to have much of a message but wields an aggressive operation (“You know what to do,” one of his field lieutenants tells his people when mentioning seeing a rival’s signs near their one of their campaign offices) and spends a Sunday going from one church to another leaving multi-thousand-dollar checks in his wake. Amara Enyia is the poised and fresh-seeming daughter of Nigerian activists who ultimately attracts more attention for getting endorsements from hometown celebrities like Chance the Rapper and (very briefly) Kanye West.

Easily jumping out from the ranks is Lori Lightfoot, a diminutive lawyer who garners the camera’s attention not just for potentially becoming the city’s first Black gay mayor but for her bracingly direct style and fearsome smarts. Next to her, seeming frontrunners like Bill Daley (whose father and brother already held the office), who has buckets of money and name recognition have a difficult standing out. Even though the election’s results can be no surprise, the chaotic randomness of how it all shakes out is still captured by James with dramatic and occasionally comic panache.

A movie that raises many questions and poses few answers, “City So Real” can feel like a riotous, fascinating, and likely irresolvable argument that you cannot help but eavesdrop on. Many of its best moments come from people grappling with the future of the city, whether they are talking in a salon of the wealthy and lettered hosted by Playboy scion Christie Hefner, or in a Black barbershop where accusations of selling out are heatedly hurled, or political operatives tussling in a crucial yet maddeningly bureaucratic fight over the legibility of ballot signatures. In the final episode, shot more quickly in the aftermath of the city’s reckoning with the twin problems of COVID and the post-George Floyd protests and rioting, the future feels somehow more fraught and hopeful at the same time.

Like the author from whom James takes his title, “City So Real” is a backhanded ode, an honest and uncomfortable declaration of a complicated love for the city where he lives, works, and draws creative sustenance. The title comes from an oft-used lament about the city from Nelson Algren’s gutter-Beat prose poem “Chicago: City on the Make”: “Like loving a woman with a broken nose, you may well find lovelier lovies. But never a lovely so real.”

Another line from Algren’s book applies here: “And Chicago divided your heart / Leaving you loving the joint for keeps. / Yet knowing it never can love you back.” There are many people in “City So Real” that love this metropolis of skyscrapers and slums by the lake. But it’s a complicated love. And like all true loves, it does not require, and frequently does not receive, love in return. [A]

All five episodes of “City So Real” are available now on Hulu.