Plenty of couples banter, woo, and fall in love in Chicago, despite the vast majority of American films locating romance elsewhere (most often in New York). But in dramatizing the first date of Barack and Michelle Obama in the summer of 1989, when they were colleagues at a Loop law firm, writer-director Richard Tanne returned to the city where the couple met and, three years later, married. Shot over 15 days last summer, Southside With You showcases a city as photogenic, dynamic, and charming as the lovers themselves.
Wisely, Tanne focuses narrowly on their date, piecing together his narrative from the president's two memoirs, Dreams of My Father (1995) and The Audacity of Hope (2006), and from various interviews. In a 2012 presidential campaign video, the First Lady describes the couple's first romantic outing as a kind of revelation: "He was showing me all facets of his character. . . . He was hip, cutting-edge, cultural, sensitive . . . " Standing beside her, the president smiles and quips, "Take notes, gentlemen." Clearly Tanne did, recording not only the day's events—a visit to the Art Institute of Chicago, a "lovely" lunch in the museum courtyard, a long stroll down Michigan Avenue, a screening of Spike Lee's just-released Do the Right Thing—but also the nuances of the deepening relationship, from Barack's flirtatious attempts to sound suave to Michelle's amusement at the same to the way they supplement each other's memories.
For the two lovers, Chicago is more than a collection of places—it's a community, which makes the film more resonant than your average romantic walk-and-talk. Tanne opens with an appealing tableau, scored to Janet Jackson's "Miss You Much," that also serves as a civic statement: black families and friends enjoy each other's company on a sweltering day in South Shore. Unlike the mass-media narrative of the south side as a gang-ridden hellhole, Southside With You radiates love, connection, and positivity. Children ride their bikes up and down the street and chase each other through sprinklers. Teenage girls eat popsicles; an older couple play cards on their front lawn. And in a sun-soaked apartment on Euclid Avenue, Michelle Robinson, a young attorney who lives with her inquisitive and adoring parents, prepares to meet a colleague from her law firm, who lives in nearby Hyde Park, for a casual outing that she insists is "not a date."
Tanne takes an evenhanded yet still flattering approach to the characters; they seem like any educated and ambitious young professionals bonding over art and culture in a city that prizes both. Barack (Parker Sawyers) has completed his first year at Harvard Law School and been named a summer associate at the Loop law firm Sidley Austin; Michelle (Tika Sumpter) is a first-year associate, recently graduated from Harvard Law herself, and Obama's adviser. Initially she balks at the idea of dating a rumored "hotshot" who is not only her subordinate but also one of the few other people of color employed by the firm. But about a month into their working relationship, he suggests that they "spend the day together," and based on that wording, she agrees. Nonetheless she wonders aloud what they have in common. Barack's response is jocular yet sincere: "We both love Chicago."
Constrained by a tight budget, Tanne takes some artistic liberties with exact locations. The Chicago Cultural Center stands in for the Art Institute, and the couple lunch in Douglas Park instead of the museum courtyard. In one touching, if fictional, scene, Barack looks on as Michelle joins a group of black drummers and dancers in the park, their figures mirroring those in Ernie Barnes's painting The Sugar Shack, which they discussed earlier at the exhibit. At sunset they walk along the lakeshore, not Michigan Avenue, probably because the Magnificent Mile has changed so much since 1989. North-siders will recognize the movie theater as the Music Box, though the couple probably went to the old Hyde Park 1 & 2 (now the Harper Theater). Their fabled first kiss outside a Baskin-Robbins occurs not at the corner of Dorchester and 53rd (the spot has been marked with a commemorative plaque since 2012) but at 53rd and Woodlawn, where the film crew turned a Harold's Chicken Shack into a Baskin-Robbins for the nighttime scene.
Tanne also resorts to dramatic license in creating and then resolving a conflict between the two lawyers. Sawyer's Barack is an imperfect character: he smokes, which does not go unnoticed by Michelle, and his dilapidated car has a rusted-out hole in the floor. While walking through the park, he passes judgment first on his late father, describing him as an unreachable alcoholic, and then on Michelle, questioning her practice of corporate law when her true passion lies in helping underprivileged women. She calls him a hypocrite, and he apologizes. But what really turns their date around is a visit to the Altgeld Gardens housing project, where Barack previously worked as a community organizer. At a nearby church, Barack, hoping to impress Michelle with his rhetorical prowess, gives a not-so- impromptu speech for the residents, who remember him fondly.
As Tanne has admitted in interviews, this visit may have occurred later in the couple's relationship, yet Barack's rousing address to the residents, who are frustrated by the City Council's resistance to building them a community center, foreshadows his later political rise. Barack encourages them to stay positive—they already have some funding they can use as leverage—and to let go of judgment (a "friend" taught him that, he says). He invokes Harold Washington and ends his speech with a glimmer of his 2008 campaign slogan, Yes We Can. "When they say 'no,' " he declares, "We say, 'carry on!' " During an invented scene at the dimly lit Water Hole Lounge, Michelle asks Barack why he came to Chicago in the first place. "To make a difference," he replies. "Politics?" she nudges. Barack considers: "Maybe."
Chicago may not be a character in the film, the way New York City is in the movies of Woody Allen, Martin Scorsese, and Nora Ephron. But Southside With You generates as much warmth for its setting as for its characters. In another poignant scene, Barack and Michelle pass a hallway in Altgeld Gardens whose yellow brick is inscribed with the names of people lost to gun violence. This makeshift memorial, Tanne understands, is just as integral to Chicago as the lakefront, the museums and movie theaters, and the Hyde Park curb where the future First Couple shared their first kiss over chocolate ice cream. In portraying two of the city's most famous inhabitants, Southside With You offers a shining and prismatic view of Chicago as well. v