Keegan-Michael Key on His Obama and Trump Impressions in ‘Don’t Think Twice’

The comedian and star of new film “Don’t Think Twice” speaks with The Daily Beast about Obama, Trump, and the future of “Key & Peele.”

Chris Pizzello/AP

Despite what you may have heard, Key and Peele did not “break up.”

Nearly one year after Key & Peele ended its five-year run on Comedy Central, fans are still coming up to Keegan-Michael Key and telling him how sad they are that he “broke up” with his longtime comedy partner Jordan Peele. “We did not break up,” he tells The Daily Beast. “We just ended the show.”

They may still be part of each other’s professional lives—including in the somewhat disappointing yet financially successful film Keanu earlier this year—but Key has made a point to branch out on his own as well. This month, he stars in Don’t Think Twice, the second film written and directed by comedian Mike Birbiglia.

In Don’t Think Twice, Key plays Jack, who gets plucked out of his New York City improv group The Commune by a late-night sketch comedy show called Weekend Live that is essentially Saturday Night Live with a different name, complete with a smarmy Lorne Michaels stand-in played by TV vet Seth Barrish. Currently 45 years old and well into a thriving comedy career, this meant Key had to transport himself back to a time in his life when he was a lowly improv performer at Second City in Detroit.

“The wonder and the excitement and the dynamism of that chapter in your life, it’s infectious when you get to revisit it,” Key tells The Daily Beast over breakfast at the Nerdist Improv School in West Hollywood, where young aspiring comedians come in hoping to become as successful as he is today.

Key says there was a heavy sense of competition among members of his comedy group when he started out. “I think the movie really accurately represents the underlying tension of what was happening,” he says. “Because everyone is looking at each other with forced smiles and ‘good for you’ and ‘so glad you got the job.’” Just like his character in the film, Key found himself in that enviable position when he was cast on MADtv midway through that Fox show’s ninth season in 2004.

Early in Don’t Think Twice, the group gets word that representatives from Weekend Live will be in the audience for one of their last shows before the theater they perform in each week is shut down for good. Birbiglia’s character Miles warns Jack not to hog the spotlight, but he can’t help himself. Key’s character breaks into his spot-on Barack Obama impression out of nowhere and in turn violates the sacrosanct rules of improv that say all members of the team must work in support of each other.

Back in his Second City days, when TV executives would show up to recruit performers, Key recalls “a real sense of the energy in the room getting jacked up to a 12.” He adds, “So, ideally every night you’re going to perform somewhere between an eight and a half and a 10. But then if you find out that Lorne Michaels is there—13.5. It jumps up.”

When Key nails his Obama impression in Don’t Think Twice it is the first time that many of his fans will have seen him do that particular character. That’s because the role of America’s first black president went to Peele on their show together, even though Key had played Obama briefly on MADtv, where they first met. Key describes that fateful decision as the only time there was serious “competition” between the pair.

They were at an impasse when Peele, who Key calls a “masterful problem solver” came up with the idea for Luther, Obama’s “Anger Translator,” who ultimately became one of Key & Peele’s most iconic characters. “What has to happen is you have to throw your ego out the window for the betterment of the show,” Key says. “Because if this Obama-Luther thing, if this dynamic works, it might go someplace. And letting my ego go in that particular situation was the right thing to do.”

Key got the last laugh on that one, appearing alongside the real President Obama as Luther at last year’s White House Correspondents’ Dinner. It was an experience that he now calls “one the great thrills” of his life. “It was surprisingly easy, because I didn’t expect the president to be so good,” he says of Obama’s comedy chops. “I always feel horrible for whoever has to host that evening,” he adds, because they have to follow a genuinely funny president.

This year, for Obama’s final “nerd prom,” that role went to The Nightly Show host Larry Wilmore, who caused some controversy when he ended the speech by referring to the president as “my nigga.” It was a move that Key says he wouldn’t have made.

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“I personally would have excised that moment from the speech,” Key says. “I probably would have cut that, ended with the last joke and then done something super sincere and then just gone over and hugged him. Maybe done some sort of dap with the president. But hindsight is 20/20, what are you going to do?”

Obama isn’t the only political figure who Key impersonates in Don’t Think Twice. At the very beginning of the film, the cast trades Donald Trump impressions when they find out that a Trump building might be replacing their improv theater. At the time they shot that scene, Trump’s 2016 campaign was still a long way from being taken seriously.

Key says he had “no idea” that Trump would get as close to the presidency as he has, joking that Birbiglia was “very prescient” to insert what would become such a timely joke in the movie. “It was not a possibility. He wasn’t going to get the nomination,” Key says in disbelief nearly a year later. “We weren’t even thinking about it and it’s become this very relevant moment in the film.”

Just last week, Key and his fellow Second City alum Stephen Colbert collaborated on a bit for The Late Show in which he played Trump’s only black delegate at the RNC. In sketches like that one and another piece on police brutality in which he appeared with comedian David Cross on Netflix’s W/ Bob and David last year, Key has found ample opportunity to explore the type of provocative comedy that he and Peele popularized on their Comedy Central show.

Does he miss having a platform like Key & Peele to comment on important news stories through comedy?

“Oh yeah, when I talk to Jordan, sometimes we’ll say, ‘Oh my God, can you imagine if we’d done this or that?’” he says. “But at the same time, that’s probably 15 percent of the time. Mostly, I’m so glad we’re done. I feel like it ended just right, just when it should have ended. People want more of it. It’s had some sort of impact or resonance. I got to perform with the president! We’ve reached every pinnacle we ever wanted and I feel like we explored things within the art form. We’ve done it. So I don’t miss it terribly.”

But that doesn’t mean we won’t see more of Key and Peele together in the near future. Being deliberately coy, Key says, “There’s some stuff brewing. You may see us sooner than later.” In a reference that most of their younger fans will not understand, he says they are “on the Pryor-Wilder program.”

“We do one, go away for a few years, come back and do another one,” he explains. “We’ll always have each other.”