Southside with You

In the late summer of 1989, Barack Obama drove from Hyde Park to South Shore in his rickety yellow Datsun hatchback to pick up Michelle Robinson, his colleague and adviser at the Loop law firm Sidley Austin, for what would become a historic first date. The short drive is the setting of the opening-credits sequence of Southside With You, an endearing dramatization of the First Couple’s initial romantic outing that stretches, like Before Sunrise, across an eventful day and night.

Written and directed by Richard Tanne, the low-budget indie—filmed in and around Chicago last summer and opening today—counts musician John Legend as an executive producer and composer; his song, “Start,” plays over the end credits. Actors Parker Sawyers and Tika Sumpter (who’s also a producer on the film) portray 28-year-old Barack and 25-year-old Michelle, respectively.

When I spoke to Legend and, shortly thereafter, Sawyers and Sumpter at the Park Hyatt Chicago last week, the mood was an emanation of the film itself, thoughtful and warm (physically, the room was cold; Sawyers kindly lent me his jacket). Love was the focal point. “It’s a love story,” Sumpter said of Southside With You, a point with which Legend and Sawyers agreed. “It’s life,” she said. “It’s moments.”

Legend, 37, has won ten Grammy Awards, one Golden Globe Award, and one Oscar, for Best Original Song (Legend cowrote “Glory” for Selma with Common and Che “Rhymefest” Smith, and performed the track with Common). “This is what I do,” Legend said. “I’m all about love and I write about it a lot. And I think it’s beautiful when you see a film that has that level of honesty and intimacy.”

“That’s what I always try to do with my songs, too, because you want it to feel real, and you want it to feel like you could be in that position,” he continued. “I think this film does a great job of making you feel like that. I think it makes you believe in love and the idea that you can find your match, and you can find someone who makes you better, and you make them better, too.”

I asked him if writing “Start” came from that place. “It came from me being in love,” Legend said. In 2013, he married model Chrissy Teigen; their daughter, Luna, arrived in April. “But also appreciating the film,” he said. “I love how simple it is, and how close you feel to them throughout the film.”

“They’ve lived these grand lives,” Legend said of the Obamas. “But this film is close and small. And I wanted the song to feel like that too.”

Legend said he wrote the song directly after watching the film. “I was listening to the music as it was leading into where my song would come in,” he said. “I literally based it on the key that was already playing, and the feeling that I was in as I was watching the end of it, and the song just flowed from me pretty quickly.”

Chrissy Teigen and John Legend at the <i>Southside With You premiere</i> during the 2016 Sundance Film Festival
Chrissy Teigen and John Legend at the Southside With You premiere during the 2016 Sundance Film FestivalCredit: Nicholas Hunt/Getty

For Sawyers, 33, and Sumpter, 36, playing a sitting president and first lady in a film—only a handful of other actors can say the same —was not as nerve-racking as one might expect. “It went from excitement to ‘Now I gotta work,'” Sawyers said. “And that work was building a character, building a real person, and not just a caricature of the president we know. It took a lot of the pressure off, just getting down to do the work.”

“Yeah, it was just fun once we got here to Chicago,” Sumpter said. “And the great thing is that we’re playing them at such an age that the public hasn’t really seen who they are, who they were at that time, other than a few videos online of their personal life. I think we stripped them down from ‘the Obamas’ of it all and went back to where they started.”

As executive producer, Legend read the Southside With You script early on and was impressed by Tanne’s vision. “We’re sure there’s going to be a big biopic about Obama later,” Legend said, “but just seeing the beginning of their relationship was pretty cool. And I think Richard did an awesome job of capturing the little intimate moments he imagined they had on that day.”

Legend also appreciated how the story emphasizes the personal rather than the political. “I don’t feel like it’s a propaganda piece,” he said. “I feel it’s truly about love, and truly an appreciation for a couple that has been just wonderful in office together.”

Juxtaposed with the “rancor and fear and darkness” of the 2016 presidential campaign, Legend said it’s difficult not to have “a sense of appreciation for the class and the grace and the poise with which the Obamas have carried themselves” while in office, which also makes the timing of Southside With You‘s release “perfect” and bittersweet.

“Because, especially in stark relief to what we’re seeing with Trump,” Legend said, “it’s like, ‘Wow, these guys really were refreshing and special, and we were fortunate to have them in the White House for eight years.'”

I told Sawyers and Sumpter that, although they looked and sounded much like the Obamas onscreen, it didn’t appear as if they were doing impersonations.

“The intention from the beginning was never to impersonate or make them like caricatures on Saturday Night Live or anything like that,” Sumpter said, “because then the whole movie could just be a disaster. It could have been really bad.”

They both laughed. “It was surprisingly good,” said Sawyers. “It could have been really bad.”

“Richard Tanne had, for me at least, an Obama meter”—Sawyers put his hand out, flat, and tilted his palm up and down—”Ah, little more, little less. That helped.”  

Saywers described seeing Southside With You for the first time at the 2016 Sundance Film Festival in January, where the movie was warmly received, as something of a relief. “The music, the cinematography”—he credited Tanne and the film’s director of photography, Patrick Scola—”I was so proud of it.”

From left to right: Parker Sawyers, Richard Tanne, Tika Sumpter, and  John Legend at the <i>Southside With You</i> premiere during the 2016 Sundance Film Festival
From left to right: Parker Sawyers, Richard Tanne, Tika Sumpter, and John Legend at the Southside With You premiere during the 2016 Sundance Film FestivalCredit: Nicholas Hunt/Getty

When I asked how he had prepared for the role, Sawyers said he’d read President Obama’s memoirs, Dreams From My Father and The Audacity of Hope, long before he was offered the part. “But of course, I reread them,” he said, “just to dig in to who this guy was by 28 years old, see what I could gather, and get inside his head.” He said he wanted to get to the root of Obama’s preternatural confidence, deduce the “why” of it: “So I could base his confidence not on, ‘I’m just a confident man, whatever,’ but more because he’d moved around, because he’d been on his own, because he’d gotten himself into good schools.”

Sumpter took a slightly different approach. “For me, it was more about taking off the Michelle Obama who everybody loves and bringing it down to the girl from the south side,” she said, “who’s been told ‘no’ millions of times about things, what she could and couldn’t do, what she couldn’t achieve.” She described Michelle as coming from a “humble and stable family,” and noted the influence of Michelle’s father, Fraser Robinson III, and his involvement in local politics. In addition, she said, “it was reading her brother [Craig Robinson]’s book, A Game of Character, which informed me of who she was at that time, and also personal accounts of people who knew her then. That’s how I got to her.”

I asked what it was like to film on location in Chicago. “It was perfect,” Sawyers said (Sumpter agreed). “We filmed on Euclid Avenue”—not on the same block where Michelle and her parents used to live, but “the block over” he said—”so you feel that driving down, like, ‘He drove down this street,’ and it just brought a whole level of realism that we could play off of.”

“And the city, the background, is beautiful,” Sawyers continued. “The skyline. . . . After the community meeting, when we’re walking . . . the skyline, ah. It’s gorgeous.”

<i>Southside With You</i>
Southside With You

Legend has his own affinity for Chicago. “I come here as an outsider and a visitor,” he said. “But with a lot of friends here.” One of those friends is frequent collaborator Kanye West. “In fact, when I meet people from Chicago, they assume that I’m from here, just because I’m friends with Kanye, a lot of times,” Legend said, laughing. “But this has always been one of the best cities for me to tour, the first city that played ‘Ordinary People,’ the first city that played ‘Used to Love U.’ People have always been supportive of me here in Chicago, so I have a special relationship with and a love for Chicago that most outsiders don’t have.”

“It’s a great music city,” he added. “Great food city.”

<i>Southside With You</i>
Southside With You

I told Sawyers and Sumpter that the film could be a play, in that it was essentially a two-hander. “Yeah, we rehearsed it—we learned it like a play,” Sawyers said. “I mean, we learned the entire script and . . . I don’t think we read through the entire thing, but on Skype, with Richard, sometimes we’d read through entire sections, like the entire first act. So yeah, it was very much like a play. But it was fun that way, to really delve into it and know every nook and cranny of the script.”

Legend also relished the experience of diving into the material. “I enjoy the assignment aspect of it,” he said, “because it’s actually easier to write a song when you have an assignment as opposed to when you’re just going to the studio and trying to write whatever comes to you, because then you’re just saying, ‘Well, what am I thinking today? What am I feeling today?’ And you’re not really sure how to channel that into a song.”

“But when you’re writing for a film,” he said, “you have a specific target that you’re aiming for. You’re really trying to base it on the spirit of the film, and the character of the film, and it actually makes it more fun to write that way than it is to just write open-ended.”

When I asked Legend about his favorite film soundtracks, his face lit up. “Oh, man,” he said. “Well, I grew up in the era when a lot of the films really cared about their soundtracks. From New Jack City to Love JonesLove Jones was really special to me back in that time period—I think I was in college at the time. First of all, it shone a light on this whole spoken-word scene that I think was cool, and it was the first film that embraced the neosoul music movement. I was figuring out who I was as a musician, and that music from the film really was important to me at that time.”

On matters of race, history, and politics—and the intersection of the three—Legend is equally passionate. His film and television production company, Get Lifted, is an extension of that passion. “A lot of the projects we take on have a kind of social relevance and political relevance, historical relevance, because that’s what I’m interested in,” Legend said. “These are the things that I’ve always read about, and that’s what I majored in at school: English with a concentration in African-American history and culture.”

I told Legend that the Obamas’ story in Southside With You reminded me of an essay in Bad Feminist by Roxane Gay (“I love Roxane!” Legend said) about the power of telling different kinds of black stories, especially positive black stories. “Yeah, it’s great to show the range of humanity in black people,” he said. “We don’t want to always be, you know, a social problem and [tied to] historical evil, as in slavery. We don’t always want to be the victim in films. That’s part of what we want to do [at Get Lifted]. We show slavery; we have the show Underground, which is doing really well”—the period drama series was recently renewed for a second season on WGN America—”but even in that show, we show black people as revolutionaries, as people fighting against the system. And I think black people, just like everybody else, want to see themselves as human, and we want to see that on the screen, too.”

Our conversation turned to the mass-media representation of Chicago being overwhelmingly negative, and how Southside With You presents a true and inspirational counternarrative. 

<i>Southside With You</i>
Southside With You

“I think people have this sense of Chicago being a war zone right now,” Legend said. “I think part of it is conservative fantasy, imagination, because they want—whenever black people get upset about police shooting an unarmed black person, they’re first response is ‘What about murders in Chicago?’ It’s the first thing they say.”

“Obviously, there are murders in Chicago, and it’s something we need to be concerned about and looking at the root causes of and trying to do something to change,” he continued. “But we know that Chicago’s not a war zone. Chicago’s a wonderful place. There are many sides to this city, and this film shows a really cool side of the city, I think.”

For Sawyers and Sumpter, Southside With You is a universal love story that defies categorization. “Walking in somebody else’s shoes is really important, and I think we’re more alike than different,” Sumpter said. “So, even if you’re not too fond of these two people, it’s a girl and a guy who are just figuring themselves out, together.”

“People walk out smiling,” Sawyers said of audiences who have seen the film thus far. “So I hope people continue to do that: walk out smiling and talking to each other.”

“It’s a great slice of life,” he continued, “and a reminder of what we can all hope to do someday, maybe meet somebody who can—”

“—make us better,” Sumpter said. Sawyers grinned. “You just finished my sentence,” he said. Sumpter laughed: “I put a period on it.”