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.

Well, that would be awesome. And there was a chance when that opportunity was right there. Maybe I didn’t have enough confidence in my ability. My agent said, “Look, they are all on vacation. You will have to wait until August or September. Or, you can go to MADtv right now.” To take a sure thing and see how it goes.

And that’s how you met Jordan.

And that’s how I met Jordan. And it didn’t work out, but there was a time Jordan had been picked to play Obama at SNL. And that didn’t work out. But we still wouldn’t have what we have now if all of those things would have happened.

Have you ever been on the 17th floor of 30 Rock?


They have all the photos of everyone who has ever been on SNL on the wall, which is amazing to look at. But one out of seven, maybe, are famous people.

It might be one in 12.

So just getting that show doesn’t automatically translate into a career.

And we did just fine! Things worked out just fine. Mike told me somebody, who shall remain nameless at this time, an A-lister who in the very near past had five enormous hits in a row.

A comedy guy?

A drama guy who did comedy earlier in his career.

Eric Bana.

[Laughs] Nailed it.

You thought you’d sneak that by me.

“You can’t slip a swarmy, good looking, comedy Aussie by me.” But, that person said to Mike, “There is no number-one person in art.” You can only do what satisfies you artistically.

You seem to have done a good job at that.

Right. There’s always some aspect of something.

To be fair, in any movie I ever watch, I know there’s a chance you or Birbiglia might show up. You two are in a lot of movies.

[Laughs.] Yes! But, I had just made a vow to myself a week and a half before I read this script, at the behest of my representative, “Keegan, unless it really moves you, you need to put a line in the sand about projects you’re picking. It’s the time in your career to do that.”

That’s good advice.

That’s very smart advice. So here’s my thing, unless tears come down my face – I can get verklempt – but unless tears stroll down…

So it only has to be two?

Two tears.

So “tears,” plural.

It has to be “tears,” plural, or I won’t do the movie.

I appreciated that your character is not an asshole. He doesn’t always read the room correctly for his big announcements, but he’s not an asshole.

And that was very important to Mike. The antagonist of the film is the situation. It’s Tallulah Bankhead and everybody in the lifeboat. The sea is the enemy. And then, of course, Hitchcock makes people on the boat an enemy.

And your character tries to help his group once he’s on Weekend Live, but he has to worry about just keeping himself on the show.

There’s a circle of friends you have to have in your life. I will talk to other people who are more successful than I am, “This is not easy and it sucks, but figure out who your friends are for real. And that’s the bubble you need to stay in.”

If you’re a featured player on SNL, a lot of times you are on the thinnest of ice. But your friends will think you made it.

The thinnest of ice. And you’re not making a king’s ransom in salary, folks. I think people need to understand that, too. It’s good to go back home to Detroit. My two best friends growing up were firefighters – in Detroit, Michigan. So, I go, “Oh, what I do is bullshit compared to what they do.” I need those people in my life. I need my cousins who all live in a farming community in Illinois who go, “How are the skits going?” You need those people in your life to keep you human.

You do an Obama impression in the film. Do you and Jordan do Obama-offs?

We’ve never done an Obama-off. I’m glad it got nipped in the bud early on who would be Obama because we almost gave Obama credit for us having a show.

We’re losing him soon.

It’s going to be rough.

He’s our Kennedy.

He’s 100 percent our Kennedy. And having encountered him a couple of times…

What’s that like? I know you’ve discussed this…

No, I will never have a problem talking about this. The best thing about him is he has such a calming influence on you. It was not surreal. I was there. I wasn’t having an out of body experience. I was there in the moment. I was, “Oh, this motherfucker got me.” He is where he is in the moment. What a straight man – unbelievable, his timing, at the correspondent’s dinner.

I love watching the clips of Obama roasting Trump at the correspondent’s dinner in 2011.

And still nailed it.

And Trump is frowning.

“I’m gonna get that guy.” What a baby.

I’m not arguing with that.

He’s a baby.

If you’re Obama, what do you do next?

I think you do the tour. I think you do the lecture circuit for a year then figure out where you want to go from there. And then go back to whatever initiative or foundation Michelle’s going to start for Chicago. Do what the Clintons did. I think the Clintons have a good blueprint with the Global initiative.

I wish he’d host a talk show.

He’d be amazing. But I don’t want him to do what Sarah Palin did.

But not on a news channel. Like a Charlie Rose type thing.

Oh, I can 100 percent see him doing that.

I’d enjoy that.

I think I’d enjoy that, too. Because he asks great questions and he’s very present with you. And he has a knack for making you feel more comfortable than you think you should feel in that situation. He’s one of those guys. But because he’s been, to a certain degree, beloved internationally – it’s the first time in a long time Europe has looked at us and said, “Oh, the States, they came to their senses” – so that’s why I feel like there should be some kind of global initiative he’s attached to. My manager said, “He should do the lecture circuit and he should have Luther be on it.” I’ll take that gig.

Mike Ryan lives in New York City and has written for The Huffington Post, Wired, Vanity Fair and New York magazine. He is senior entertainment writer at Uproxx. You can contact him directly on Twitter.

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