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