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‘City So Real’ Is Exactly What Everyone Should Be Watching This Weekend

Steve James' five-part docuseries on Chicago's 2019 mayoral race is now the most prescient and meaningful docuseries about 2020 America.

Amara Enyia holds a press conference to announce her Chance the Rapper endorsement. (Chicago Story Film, LLC) City So Real Nat Geo Hulu

Amara Enyia and Chance the Rapper in “City So Real”

Chicago Story Film, LLC

Long before Kanye West tardily disrupted the 2020 presidential election, the pioneering force in American hip-hop put himself smack in the middle of Chicago’s crowded 2019 mayoral race. West endorsed candidate Amara Enyia at a “pop-up” rally, standing quietly next to fellow supporter Chance the Rapper and behind their progressive candidate as she spoke to a small crowd from the sidewalk. These celebrity endorsements were meant to help boost awareness, but even then, questions were asked if West’s support of Donald Trump would negatively effect the young, Black candidate’s attempts to court Black voters.

And Steve James was there.

Before the GOP’s attack on voting, including inflated claims of voter fraud and the outright theft of people’s ballots, delegates for Chicago mayoral candidates sat around a computer and made knowingly false claims to try to boot their opponents from the ballot entirely. Lawyers cited mistakes on pages that didn’t exist, and signatures were challenged despite the signatory sitting right next to the challenger; not one but two candidates had signatures ruled illegitimate that were given by their own mothers.

And Steve James was there.

Before George Floyd was murdered by Minneapolis police officers, sparking nationwide protests and demands to defund the police, Chicago cried out for justice, reform, and abolition when 17-year-old Laquan McDonald was shot 16 times by Chicago Police Officer Jason Van Dyke. The years-long trial culminated with a prison sentence of six years and nine months, but the officer was not found guilty of official misconduct. The all-too-familiar cycle only deepened divisions; the city’s old guard cried out for more law and order, while reformists demanded substantial change.

And Steve James was there.

Before Tuesday’s election, the director, producer, editor, and cinematographer behind “Hoop Dreams” and “America to Me” will debut his latest work, “City So Real” — an impossibly prescient look at an American city at a crossroads, just days before America decides which path to take for the next four years. All of the aforementioned events are included in the five-part series, four of which have been in the can since January when they premiered at the 2020 Sundance Film Festival. Even then, before the latest protests, before the latest voter suppression tactics, before Kanye Vision, it was clear that Chicago’s problems were America’s problems, that its strengths were America’s strengths, and that “City So Real” had captured a moment in time that resonates beyond cities and states, to the whole country.

City So Real Nat Geo Hulu Police stand outside of Wrigley Field. (Chicago Story Film, LLC)

Police stand outside of Wrigley Field in “City So Real”

Chicago Story Film, LLC

But nine months later, things have changed. Nerves around November 3’s elections and the ongoing pandemic have made consuming anything related to either one more difficult than ever. Yes, viewers are soaking up breaking news, whether it’s because they have to or they can’t help themselves, but when it comes to optional entertainment, escapism reigns. Between the 24-hour news cycle, on-the-ground social media coverage, and an arrested audience sitting at home processing everything in real-time, the recurrent problems of a slow-to-adapt society have been well-documented. When it comes to a documentary like “City So Real,” is there an appetite to reflect on how we got here, just days before we find out where we’re going?

Yes, and James provides the reason why. Well, there are a few, really. For one, “City So Real” isn’t repetitive or reductive. James has always been a filmmaker genuinely interested in spending time with his subjects, and the length of his latest docuseries makes the most of his attentive patience. Hearing from 21 different political candidates may sound like a particularly unpleasant way to spend five hours this election weekend, but it’s surprisingly rewarding — and watchable. James’ car-ride discussions with Lori Lightfoot and post-press conference footage of Toni Preckwinkle shed the speechifying for innate human interactions. You get a good idea of who they are, or at least what motivates them, and better still: Their campaigns are mostly framed by their would-be constituents.

There are telling trips to two barbershops: one Black-owned and -operated, the other a haven for ex-cops; man-on-the-street interviews illustrate the disparity of community engagement between neighborhoods; even capturing the first half of a (notorious) Bears game from a South Side bar and the second half on the North Side goes a long way toward grounding “City So Real” in a tangible reality. James lets you hear from the people and the candidates as people, rather than via their carefully crafted public personas. (Even Bill Daley, who isn’t a big presence in the series, is revealed through crystalizing moments during press appearances.) Political bloviating often hinges on hypothetical plans for the future, but “City So Real” is firmly rooted in what’s actually happening.

Neal Sales-Griffin shakes a judges hand at a voting site. (Chicago Story Film, LLC)

Neal Sales-Griffin in “City So Real”

Chicago Story Film, LLC

With that very much in mind, James returned to his favorite city to shoot an additional episode covering the latest protests over police brutality as well as the way COVID-19 has reshaped Chicago. Episode 5 was captured over the summer, and James revisits some of his subjects in person as well as via Zoom. There are sit-down interviews with the mayor and a lengthy trip to the cop-friendly barbershop. There’s first-hand footage of peaceful protests that turn violent and first-person commentary on the local government’s role in the escalation. Clocking in at nearly 90 minutes, it’s a feature-length episode that connects the predictive past chronicled in the first four episodes to our difficult present. Originally intended as a kind of postscript, James wisely uses the additional time to emphasize how big picture problems have drastic effects on individuals, as well as their communities, all while keeping the voices of the voiceless elevated.

“City So Real” is perceptive and insightful, carefully cut together and impressively encapsulating. I haven’t seen, nor can I imagine, another show that captures 2020 so thoroughly or makes reliving such a heartbreaking period so naturally watchable. But that’s not the main reason you should see it right now. “City So Real” manages to acknowledge and articulate the many divisions tearing us apart and still form a unifying message. It’s a way to engage with the world as it is without letting that reality break you down. More than anything, it’s a way to feel like you’re part of a community during a time when so many of us feel completely cut off.

Because Steve James was there, you can be, too.

“City So Real” premieres all five episodes Thursday, October 29 at 7 p.m. ET on Nat Geo. The full series will be available to stream on Hulu Friday, October 30.

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