Keegan-Michael Key Has Obama’s Post-Presidential Career All Figured Out

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It’s funny to listen to Keegan-Michael Key talk about Barack Obama – in the sense that, in person, Obama has a way of making you feel more comfortable than a person should be feeling. Now, Keegan-Michael Key isn’t the leader of the free world (at least, that we know of), but he can pull off a similar trick. Midway through this interview, I started thinking things like, I wish I were friends with Keegan-Michael Key. Because he has a way of making you feel like you’ve been friends for years. That’s a tough trick to pull off with strangers.

It’s a big few weeks for Key. On April 29, his feature film with Jordan Peele, Keanu will hit theaters. (We have a whole other forthcoming feature with Key and Peele together just for that.) And now, at the Tribeca Film Festival, he co-stars in Mike Birbiglia’s second directorial effort, Don’t Think Twice.

Key plays Jack, a member of a New York City-based improv comedy troupe, who gets the call to be on Weekend Live, which in the universe of Don’t Think Twice is basically Saturday Night Live. And, as expected, the rest of his troupe that he leaves behind has to deal with the emotions that come with watching someone else “make it.” And, of course, this gives us an excuse to dive back into Key’s own comedy origins and talk about his personal experience with missing out on Saturday Night Live and how that led to him meeting Jordan Peele.

You get to do the SNL-type, “Oh, I’m just hanging out… wait, a camera? Hello there!” opening credits.

[Laughing.] With the bike!

You didn’t ham it up. It felt like the real thing.

This is why I love Mike as a director so much. He’s like, “I’ve seen you do it on Key & Peele. You know you can do it. You’re a dramatic actor. I’m asking you, Keegan, just walk down the street. Just carry the bike. Don’t go fucking nuts.”

But you like going nuts.

I do.

When you show up in a cameo, you’re usually doing something nutty.


Like in Let’s Be Cops, you’re going nuts.

And that’s the nuttiest. An accent and a grill, tattoos on the face and hair. I actually do prefer the challenge of getting across something with a wink or a shift of the eyes. And there were many moments in this movie where it was helpful for Mike to rein these moments in. Technically, I should know better. I’m Sanford Meisner trained, I should know better.

This movie strikes a chord because everyone has felt professional jealousy.

Absolutely. Jake Johnson and I were talking one day and he’s like, “You’re doing that Birbiglia movie, right?” He’s like, “That is rough stuff. I read that script. That’s rough stuff.” Because what happens is, your dream is coming true for someone else. Your personal, specific dream is coming true for another person. There’s this lovely little cocoon of family where we all live in the same cult. And the cult is, “yes, and…; yes, and….” But then there’s this looming specter outside of it saying, “You, too, could become famous.”

When you were on MADtv, did you feel that towards SNL?

There was a moment when I was in my late thirties when my agent called me and said, “You said you wanted to make movies. If we can get you an audition at SNL and you got picked, then that’s part of the deal. You’d have a contract with Lorne to make a certain amount of movies with Broadway Video.” I remember there was a moment I went, “this is my home now.” Los Angeles is my home and I feel like I’ve staked my claim and I don’t know if that’s the next step anymore. And up until that moment, I still looked afar to the East. I want to stand at Studio 8H where Aykroyd and Belushi stood.

You’re going to get to host someday.

Well, that would be lovely. That would be the most amazing thing and make it come full circle.

Within three seasons.

Within three years, you say?

Well, this season is almost over. So I think it should be next season. But I also want to hedge my bet.