‘City So Real’ chronicles life in Chicago, from mayor’s election to COVID-19 pandemic

Hosted by

Steve James has been making documentaries for more than three decades, and he’s used to people flagging him down when he’s filming, hoping they’ll get to appear on camera. He says he often gracefully declines these offers.

But James had a different approach for his latest project, “City So Real.” He describes his five-part docuseries, set primarily during the 2019 race for mayor, as a “mosaic portrait” of Chicago. To make the series, James went out to the streets of Chicago to capture impromptu slices of life. He says his small crew often left in the mornings with no idea where they would end up or what they would capture. 

Some of the film’s most emotional moments were captured spontaneously.  In one scene, an Uber driver talks about her encounter with a racist man earlier that day. In another scene, an unhoused woman sings for patrons of a Chicago restaurant during the holidays.

James and his crew also followed many of the mayoral candidates during their campaigns. Though with 14 candidates, he admits they couldn’t follow every contender as closely as they would have liked. He ended up focusing  on the eventual mayor Lori Lightfoot well before she was seen as a serious competitor.

After showing  the series at Sundance, James was on the hunt for a buyer when the COVID-19 pandemic hit. He decided to shoot a postscript for the series, which eventually turned into the series’ final episode.



  • Steve James - writer and director of “A Compassionate Spy”


Kim Masters


Kaitlin Parker