At his final White House Correspondents’ Dinner back in April, President Obama strolled up to the lectern and raised a finger skyward, beckoning his audience to drink in the lyrics to Anna Kendrick’s “Cups”: When I’m gone, when I’m gone / You’re gonna miss me when I’m gone. He flashed that unmistakable grin, looked out at the crowd of assorted journalists, politicians, and head-scratching celebs, and quipped, “You can’t say it, but you know it’s true.”
Yes, the Obamas are having a moment. Following the Democratic National Convention, an outing that boasted dazzling speeches by POTUS and FLOTUS—as well as a whooping, star-spangled Meryl Streep—President Obama’s approval rating rose to 54 percent, its highest number in 3½ years. And Michelle Obama’s speech was so damn stirring it left many wondering aloud whether she’d run for political office. Now, to add compliment to flattery, a lovely new film is hitting theaters that documents the first couple’s first date. It’s called Southside With You, and shouldn’t work nearly as well as it does.
Written and directed by Richard Tanne and executive-produced by John Legend, the film traces a young law associate by the name of Barack Obama (Parker Sawyers) and his day-long mission to woo his skeptical supervisor, Michelle Robinson (Tika Sumpter). It’s 1989 Chicago, and as they amble through the park, into a museum, and ultimately to a screening of Spike Lee’s Do the Right Thing, they share their life stories and begin to fall in love. The journey is Linklater-esque, and the performances, particularly Sawyers’s, are pitch-perfect. He so closely resembles a young Obama that there are moments where you think you’re watching the real thing.
“You forget that he’s not Obama sometimes,” chuckles Legend, chatting with The Daily Beast.
The 37-year-old piano prodigy turned Grammy-winning crooner turned prolific film and television producer had been monitoring Tanne’s project since the script stage, and formally came on board as exec producer after filming was completed. He viewed it as similar in a way to the Martin Luther King Jr. biopic Selma, in that they both tell “important stories of important periods in time.” That film, helmed by Ava DuVernay, won the singer-songwriter an Academy Award for Best Original Song (he composed an original song, “Start,” for Southside as well).
“There was a good piece in The New York Times recently about what a good example they’ve set as a couple, regardless of your politics,” Legend says of the Obamas, who’ve raised two fine young daughters, Malia and Sasha. “Just as people, as parents, and as a family, they’ve been a great example—and an aspirational one for not just people in this country, but people all over the world. For us all to be privy to a film about how that started is pretty cool.”
Legend, who sang the will.i.am-produced Obama election anthem “Yes We Can” back in 2008, describes how the Obamas’ presence as the quintessential all-American family is something that we’ve taken for granted. For example, this year’s Republican nominee and ex-reality-TV star Donald Trump trotted out five kids from three different wives at his ominous convention.
“Obviously there’s a double standard and it’s to some extent a bit of root for your own side, and so you’ll criticize things on one side that you wouldn’t on your own team,” says Legend, adding, “To some extent there’s a double standard that has racial elements as well. They were held to a much higher standard, and they exceeded that standard.”He pauses. “The Obamas have been a great example for the country and I think people are getting a bit nostalgic for that now when they see what some of the alternatives might be.”
Legend is now a family man, too. His troll-slaying wife, Chrissy Teigen, recently gave birth to their first-born, a beautiful baby girl named Luna. And as far as 2016 goes, Legend says he is with her as well.
“I’ve fundraised for Hillary, and I’ll be voting for her,” says Legend. “I don’t think we should be electing Donald Trump as president and I’m supportive of Hillary’s campaign. There’s nothing that can shock me anymore, but at this point, Trump’s made it very clear how his temperament is, how his personality is, what his level of intellectual depth is when it comes to policy, and he’s made it abundantly clear that he’s utterly unqualified to be president—no matter what your political views are.”
He isn’t finished. “Trump’s been a public personality forever and that’s fine if you want him to be a reality-TV host, but if you want him to be president there’s a different standard,” Legend continues. “And remember, his entry into being a Republican was questioning the citizenship of the first black president. We know who he is, he’s made it clear who he is, and now it’s time to show up and vote. He never was a winning candidate. What he’s selling is only palatable for a minority of the country. It might be the majority of the Republican Party, but it’s not the majority of the country.”
Now, Legend is not only a piano wizard, having played on the track “Everything Is Everything” off The Miseducation of Lauryn Hill as a teen, but he also graduated from high school as salutatorian at the age of 16, and had his degree from the University of Pennsylvania by 20. While at Penn, he says he crossed paths with Donald Trump Jr.—the son of the Republican nominee.
“I was at Penn at least at the same time as Donald Jr., so our careers at Penn intersected,” Legend recalls. “He was like a year behind me. I never interacted with him. I knew he was on campus because he was the son of a famous person, but I didn’t really know or want to know anything about him at the time.”
Our chat eventually comes back to Southside With You, and the legacy of President Obama. According to Legend, he’s done an exceptional job as commander in chief.
“He’s increased access to health care, taken job creation to a whole other level, lowered the unemployment rate, and done a lot to combat climate change,” says Legend. “And at the same time, he’s been a very great president to represent our country. He’s someone we can be proud of, and his family is one to be proud of as well.”