City So Real movie review & film summary (2020)

For decades, James has been the best documentarian in Chicago, bringing his city to life in projects like “Hoop Dreams,” “The Interrupters,” and “America to Me,” but “City So Real” is arguably his most ambitious project to date, wedding the political system of the Windy City to its past, present, and future. Some of it could be considered dry—you will learn more about the signature verification process to get people on the mayoral ballot than you could imagine—but it has a remarkable cumulative power, one that feels amplified by the events of 2020 in unexpected ways.  

James and his team jump right into a heated mayoral race as it’s getting off the ground in 2018, instantly divisive because of the murder of Laquan McDonald, and how poorly the entire situation was handled by Mayor Rahm Emanuel. Sensing the incumbent mayor could be defeated, the field started to fill up in unexpected ways, and then Emanuel made the surprising move of dropping out of the race, announcing he wouldn’t run for reelection—leading to an explosion of candidates. James documents key events in the race like Chance the Rapper’s endorsement of Amara Enyia but it’s much more of a fly-on-the-wall approach to politics, detailing the daily existence of a campaign like strategizing, press conferences, and even going door to door to get votes. Interestingly, Lori Lightfoot, who would eventually win the landmark race after becoming the first out candidate in Chicago mayoral history, starts out as background player in early episodes as candidates like Willie Wilson and Bill Daley dominate the story, but it’s fun to watch her profile rise through the series.

“City So Real” is not purely a political piece. A lesser filmmaker would have focused exclusively on campaign events and promises, but James connects those to not only other major events from 2018-2020 but everyday life in the city. It’s a series that can go from a commentary on corruption in Chicago politics to interviews at a bar while fans watch a crucial Bears game to a segment on the death of a police officer. It’s a tapestry of life in Chicago that is entertaining in its individual moments but gains much more power when considered as a whole. Kind of like the city itself—a place that values its vibrant communities but also how they come together in times of crisis.

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