Southside With You

Southside With You is a gently fictionalized recounting of Michelle and Barack Obama’s first date back in 1989 when they were working together for the summer at a Chicago law firm. She was a junior associate. He was an intern from Harvard. They walk and talk and fall in love.

Southside With You is a delightful, romantic, breezy film. Being who they are, they talk about their dreams of bringing positive change to the inner city and confess the way they have strayed from that dream by working for a big law firm. They discuss civic responsibility and the purpose of personal ambition. Due to Tika Sumpter and Parker Sawyer’s impression-lite performances and writer/director Richard Tanne’s earnest script, these civic-minded conversations are endearing. We see the Barak and Michelle Obama that brought hope to so many. We feel that hope rekindled again.

Southside With You works like a new episode of The West Wing. The future Obamas walk and talk and spur each other to being the best version of themselves. You want their relationship to succeed, because it comes to stand for the possibility of our nation succeeding. They are honest with each other and others about the challenges facing the southside of Chicago and, by extension, the nation. Their optimism feels honest as well.

In addition to the sense of civic responsibility, the future Obamas’ first date revolves around African-American art. They visit a gallery showing African paintings and sculpture and talk about TV shows with black casts. Michelle dances with a group of African drummers in the park. They debate the best Stevie Wonder albums. They end their date with a trip to the movies to see Spike Lee’s latest (at the time), Do the Right Thing. By featuring all this African-American and African art, the film is both associating itself with those works of genius and, more importantly, associating the Obamas’ relationship with these masterpieces. The Obama romance is cast as a world-changing work of art.

All this is meant to be inspiring. It was for me. Southside With You made me want to take long walks with my wife and discuss how we could change the world. I can only imagine how the film will play for black audiences. We don’t often see sweet, romantic films like this about black couples. It helps that it is the Obamas, of course.

You’re probably wondering if the Obamas have seen Southside WIth You and if so, what they think of it. According to the director, they haven’t seen it, but they do know it exists, and they are puzzled by its existence. Icons are seldom aware of their own status.