Larry Wilmore on Hosting Obama's Farewell Dinner, How Many Trump Jokes Are Too Many

Andrew Hetherington
Larry Wilmore

Ahead of the outgoing president's final White House Correspondents' Dinner on April 30, the 'Nightly Show' host shares his thoughts on the likelihood of another black president: "It's like when a black sitcom ends, you don't see another for a long time."

A version of this story first appeared in the May 6 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

Even before he landed his own TV show, Larry Wilmore had zeroed in on a gig he really wanted: hosting the final White House Correspondents' dinner during President Obama's administration. "I made it known to my people a few years ago that I would hopefully be in contention," admits the Nightly Show host, 54. "Believe me, I didn't think it would happen." But on April 30, it's Wilmore who will share a table at the Washington Hilton and likely many laughs with the outgoing president. He talked to THR about how many Trump jokes he'll dish out and why he hopes Kanye West is in the building that night.

How do you pay respect to Obama's historic presidency while also making people laugh?

You pay respect by being completely disrespectful. You spread that disrespect all around the room and just have fun. I'm very honored to do it. I'm the same age as Obama, but we kind of went on different paths. We graduated high school at the same time. So for me, it's kind of surreal if I really sit and think about it. Man, I never would've considered a peer, a brother growing up in the era that I did, would be president someday. I remember it was a big deal when Thurgood Marshall was named to the Supreme Court. I thought that was the biggest thing for a long time.

How did you get the job as host?

It's a bit mysterious how these things work. They have a different chair person for it every year. And I'm sure I was presented like other people, but how they actually make the decision is a mystery to me. I was so excited when I found out.

You attended the dinner last year, so you know what to expect. What was your experience like? Who were your dinner companions?

I was a guest of David Remnick of The New Yorker. I had done an event with them that was fun and they invited me to sit at their table. Sitting there with all that Washington power in the room is interesting. I'm used to all the Hollywood stuff, but not D.C. These are the people who are making the decisions. And I had never met the president before, and I was in a direct line to him. It was very surreal. I was looking at it from a different point of view, also. I was watching Cecily [Strong] work, and I'm dying every time I feel like something doesn't work and I'm cheering when something does work. It was almost like surveillance, in a sense.

You mentioned Cecily Strong, who hosted last year. What did you think of her hosting outing?

She did a good job. It was so tough what she had to do. Obama is really funny, and he crushed it before she came up. His "anger translator" bit with Keegan Michael-Key of Key & Peele was hilarious. I thought she did a great job to follow that, and she was fearless. She had some great zingers.

You have said Seth Meyers and Colbert stand out to you for their dinner outings. Have you reached out to either for advice or suggestions?

I have not had a chance. That's a very good thought — maybe I should. Joke for joke, Seth was one of the funniest I've seen. There have been some really funny people who have done it but his was really great. He did a takedown of Donald Trump with Donald Trump sitting right there. Stephen's was funny for a whole different reason. No one knew what the joke was. A lot of people assumed he was a conservative comedian because his show had only been on for six months to a year, maybe. It was pretty fearless; almost like performance art.

Late-night hosts, including you, say the challenge of campaign season is how quickly things change — you have to be writing jokes up until minutes before showtime. Will you be doing the same for this gig?

I have to. I have no choice. I'm the kind of person who will tinker with stuff right before I go on, which is crazy. The timing can be infuriating because you might craft a really good joke, and then, sorry, it's canceled out by something that just happened. Or how about this: You have a great joke and then the president does that joke?

Big question: How many Trump jokes are too many?

The answer is close to 900 or 1,000. It's a conundrum writing a Trump joke because he's such a caricature himself. Repeating what he says is probably funnier than anything you could write. It is a challenge, but it's also fun to come up with Trump stuff. I love it when he gets mad about people making fun of him. He's got a lot of nerve. He's said he's a billionaire many times; why would you be mad at people making fun of you? What do you care?

In your lifetime, do you think you will see another black president?

It would be highly unlikely. It's like when a black sitcom ends, you don't see another for a long time. It would be nice if [Obama's presidency] continues to open doors for other firsts to happen. Just last night, they showed the Jackie Robinson documentary on PBS. Man, you look at the world and think, "That wasn't that long ago." Look at what this country was — we didn't let black men play baseball, for Christ's sake. That's a game. That was an issue, playing a game. Now we have a black president.

Do you still get nervous, even at this point in your career?

I have to do jokes for the president of the United States. (Laughs.) I've never even considered that as a possibility of something that happens. The reality of it is almost devastating because I don't want to eat it. The night of all nights. This is the night you have to make sure you are on point. So yeah, I'm very nervous about it. But really, nervous and excited.

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