Southside With You is a Date Movie about Impossibly Famous People

Southside with You is simply a date movie. It just happens to be about impossibly famous people. One of this film’s many strong accomplishments is its ability to enamor and enchant you often to forget that the two main characters are a future President and First Lady of the United States of America. That is no small feat, and one accomplished through flourishing grace from the filmmakers and magnetic allure from its lead performers.

Director Richard Tanne’s film asks you to step back and remind yourself that Barack and Michelle Obama are still people and not just their former titles and offices. Like anyone else, they too were ambitious and career-minded young people once. They were cultured and cultivated into the self-made people they are today by both their individual and shared history. Every love story begins with the catalyst of a first date and Southside with You chronicles one particular Chicago summer day in 1989.

Three years before they were married, Michelle Robinson (Sonic the Hedgehog‘s Tika Sumpter) and Barack Obama (TV actor Parker Sawyers, currently of P-Valley) were colleagues at the same Chicago law firm. Barack was a junior associate fresh out of Harvard and Michelle was his senior adviser. She specialized in trademark cases downtown while Barack put his passion towards stumping for neighborhood issues, working as a community organizer in the Altgeld Gardens housing projects on the far south side of Chicago.  We meet one primper (her) dressing to impress at home and one procrastinator (him) chain-smoking and motoring up late in a rusted-out Datsun.

Michelle has accepted an invitation from Barack to attend a citizen meeting in the Gardens. In true superior-to-subordinate fashion, she insists constantly that this is not a date. That doesn’t stop an occasionally ogling Barack from turning on the charm to win her respect and attention. He plans out the day and fills their shared time with stops around Chicago to take in some culture, walk and talk shop, compare anecdotes, push boundaries, share a meal, and reveal pieces of their driven personalities and character-building upbringings that brought them to law. Their day of peaks, valleys, challenges, contributions, contention, and compromise culminates with a trip to see Spike Lee’s topical Do the Right Thing and an ending stop for ice cream.

Barack looks over at Michelle during a movie in a theater.

Between both Barack and Michelle, you have two highly-educated, culturally rich, and determined workers. Both arrive to each other with different ideas and beliefs about how to best fit work, family, aspirations, and the greater good of community work into their lives. No matter which approach, both seek to do more and build the right priorities to make the the most of their time. It’s not just efficiency of time. It’s quality of time.

In the immortal words of Van Wilder, first dates are interviews. Michelle can dodge the workplace gossip all she wants, but she is judging Barack’s potential or she wouldn’t be along for the day. He is doing the same, looking up at her success and trying to figure out what unlocks her respect and affection. However, both of them pigeon-hole each other and step into hypocrisies with some uninformed judgments. Through an intellectual and meditative day growing together, both learn judgments have to be deserved and can only be made by people who have earned the right to give them.

Barack hugs Michelle walking down the street.

If you ever want an interesting look into a married couple, ask them “Hey, how did you two meet?” There’s a good chance their first date is part of a lovely and personal yarn. They are almost always great stories. Watch them reminisce on unforgettable moments. Watch them flutter with rekindled feelings. Call me a softy, but I believe just about every married couple has a love story fit for a big screen movie. Real-life nuances and unfiltered emotions beat fancy scripts and fictional acting every time. Southside With You plays like one of those recounted dinner table stories for all of us to see and hear.

Barack and Michelle look at a display of African-American art in a museum.

This directorial debut and second screenplay of Richard Tanne (who went on to write Chemical Hearts last year) comports itself with a winning amount of charm and empathy. Paced to only cover a single day, Southside with You is dialogue-driven and captivates as well as any entry of Richard Linklater’s Before series, the quintessential blueprint for this type of romantic film. Tika Sumpter and Parker Sawyers bring engaging and vibrant performances, the two match mannerisms with the real figures but do so without preachy caricature.  Who they are melts away as the their words breathe life into how these two tick on the inside, not how the public image is presented on the outside.

Tanne’s journey beautifully balances a soft brush for romance and humanity with the right amount of light shed on the inescapable realities of the urban and racial challenges that existed for the two then that unfortunately remain today in the city of Chicago. Southside with You is not a foreboding Star Wars prequel where every prophecy is on the nose with painfully obvious and forced destiny. Approachable emotion is front and center instead. Slow pushes, pulls, and zooms of interior and exterior closeness, from cinematographer Patrick Scola, and set to a guitar-tinged score from Stephen James Taylor, frame and produce quiet pauses of shared reflection that cement the film’s power. What remains after the John Legend serenade in the end credits is an inspiring love letter to its subjects, the city, and the character traits that make their story special.

Southside With You is available currently to stream on Hulu Plus.

Written by Don Shanahan

DON SHANAHAN is a Chicago-based Rotten Tomatoes-approved film critic writing here on Film Obsessive as the Editor-in-Chief and Content Supervisor for the film department. He also writes for his own website, Every Movie Has a Lesson. Don is one of the hosts of the Cinephile Hissy Fit Podcast on the Ruminations Radio Network and sponsored by Film Obsessive. As a school teacher by day, Don writes his movie reviews with life lessons in mind, from the serious to the farcical. He is a proud director and one of the founders of the Chicago Indie Critics and a voting member of the nationally-recognized Critics Choice Association, Online Film Critics Society, North American Film Critics Association, International Film Society Critics Association, Internet Film Critics Society, Online Film and TV Association, and the Celebrity Movie Awards.

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