Chicago as the Third Wheel on the Obamas' First Date

Writer-director Richard Tanne’s debut film, Southside With You, chronicles the emotional and intellectual courtship of two now-famous people: Michelle Robinson and Barack Obama, who share a first date in Chicago’s South Side in the summer of 1989. The two co-workers at Sidley Austin law firm adventure into the city from Robinson’s house in South Shore to an art exhibit, a community meeting at a South Side church, and a downtown screening of Spike Lee’s Do the Right Thing. As the future First Lady and future President discuss their hopes, dreams, and goals, the city of Chicago provides a backdrop for their conversation about race, family, and community.

In many ways, it’s an utterly conventional (and critically well-received—The New Yorker’s Richard Brody calls it “an authentic joy”) date-night movie, but Southside is also a surprisingly thoughtful portrait of how two ambitious people relate to a troubled city, a place where they both want to help bring about change. CityLab recently spoke with Tanne about how the Chicago of 1989 influenced the film, and the presidency.