“You never know what your hold music is,” Larry Wilmore mused to me, when I spoke to him on the phone this week. I had made a comment about how jazzy the music was, because it was just a longer version of the theme to his late-night news-satire show, “The Nightly Show With Larry Wilmore,” which airs directly after “The Daily Show” on Comedy Central. I shouldn’t have been surprised that Wilmore—the elder statesman of late-night comedy—would approach even a tossed-off remark about hold music with the same thoughtful consideration on perspective and privilege that he brings to his show on Comedy Central.
Now Wilmore is about to step up to a slightly more exalted audience. On Saturday, the comedian will be the featured entertainment at the White House Correspondents’ Dinner, the fête hosted by the White House Correspondents Association that is part schmoozing, part comedy roast, part awkward D.C. nerd prom. It’s a weird scene, and one that has come with its own memorable controversies, whether that is Stephen Colbert’s in-character delivery from 2006 or the 2011 roasting of now-GOP-frontrunner Donald Trump. Wilmore is more of a behind-the-scenes TV writer or an affable late-night anchor than a stand-up comedian delivering a monologue, so it will be a bit of a change of scene for him. But with this election, and these candidates, it was too delicious an opportunity to pass up. I spoke with the comedian about President Obama’s humorist stylings, the state of late-night comedy today, and what’s really up with Donald Trump.
Because you’re speaking the White House Correspondents’ Dinner for President Obama’s last term, you’ll be on the scene for the official “unblackening,” as it were.
Yes, I know, I know! This really is it.
How does it feel?
It is very nerve-wracking! When I first found out I immediately got nervous. [Laughs.] It's like, be careful what you ask for, you know. I think it's the whole honor of doing it and the realization of all the aspects of it, including the fact that is, Obama's last year. I've always seen his presidency as a historical one first and foremost.
And the other thing is, the president is really funny, so you got to bring your game. You're following a guy who can kill and give you a laugh. You have to laugh at the president because he's the president, right? It's the ultimate laughing at your boss. So he's guaranteed to kill. He's gotten funnier over the years, his style has gotten better. And all that really pisses me off. Because it's just not fair! He should be stiff and awkward, and everything. But he's cool! How do you follow a president who's so cool and funny, right? Right. So that's what I'm up against.
And as you’ve observed, he also has no fucks left to give.
It’s zero. Zero! He's in the fractions of fucks-left-to-give. [Laughs, sighs.] Oh, man, it's so amazing.
The White House Correspondents’ Dinner is its own special atmosphere, and as you know already, the New York Times posited that the way the Correspondents’ Dinner went in 2011 was one of the motivating factors for Donald Trump running for president. Which has got to be a weird thing to know.
I feel like if there was ever a reason to get rid of the White House Correspondents’ Dinner, that would be the reason. I mean it should have been... [Laughs.] You don't ban muslims — ban the White House Correspondents’ Dinner, and we wouldn't be in this mess, right? God, put your priorities in the right place, Congress, is what I'm trying to say.
It’s a comedy roast, but here is this room full of people who aren’t used to having their egos taken apart.
Yeah, I know.
As a comedian, that’s a very interesting atmosphere to walk into.
Well, I figured, too, that people go in there knowing what it is, so you kind of have permission to go after people. As a stand-up, I was never the type to really go after people in that catty kind of whatever. We do some of it in our show, because we take a stance on the show. But it's not normally in my personality. So it's kind of fun for me to do that type of thing in a stand-up room, because we have permission to. [Laughs.] I mean, how many times do you get to make fun of the president—to his face, right? You used to get your head… beheaded for that type of thing, not too long ago. You know, court jesters.
What do you imagine the White House Correspondents’ Dinner in Trump's presidency will be like?
Oh my God. Can you imagine him sitting on that dais? Because he can't take a joke. I mean, the one you talked up, the Seth Meyers one—that's probably my all-time favorite. Just because of the whole Trump thing, because both Obama and Seth went after Trump. And it was so funny to see his face, just—can't take it, can't take it, can’t take it, can’t take it. [Laughs.] It was so hysterical. Can you imagine him as president sitting there? Now that's one you want to do. Now if I was doing it and Trump was president, I would do the entire thing about Trump. And I would make it seem like I was not going to do a joke about him, but then the punchline will be about Trump. [Laughs.] Like no matter what the set-up was, the punchline would be Trump.
You described Trump in an almost poetic way on CBS News, in response to Trump attempting to be a more conventional politician: “a substantive fool.”
Yes, exactly. [Laughs.] Instead of a shallow one, he'll be a substantive fool. He's still going to be a fool.
He's raised shallowness to the level of idolatry. The "upper-crass," is really what it is. Where crass itself is being honored. There's no stuff behind it, it's not there as a strategy to really pull back and see the truth, or something. Like, if it was a strategy, I would call him fucking brilliant. But it's not. It's just a celebration of crass itself. I mean, he's not alone, he's just the super-ego example of that. How much of our culture is the upper-crass right now? I guess I'm part of it, too. We deal with crass a lot on our show. Sometimes undressing it, of course. Sometimes participating in it. But he is definitely the ultimate, id example of it.
Is the Larry Wilmore of “The Nightly Show” going to be the same Larry Wilmore at the White House Correspondents’ Dinner?
Yeah, kind of. I guess it's close, because that is the TV version of me. But it's more a stand-up/monologue type thing, which I don't really quite do on the show. It's more of an editorial on the show. I guess it’s the younger brother of it, or the older brother. I guess. I don't know if it's weird for me to say that. [Laughs.] It's tough, too, because I know some of it is—this isn't really a joke, it's kind of an attitude. But I guess that's okay, too. I didn't try any of this out in comedy clubs or anything, so really, I'm just testing it out on the audience.
And how is the non-TV, non-persona Wilmore is thinking about this election?
My opinion of it is very close to the TV Larry Wilmore. [Laughs.] Very close. I really think that Donald Trump is a dangerous individual, I really do. And for the big picture, not for what he believes in. It's because he's thoughtless. He's not only thoughtless, he's impulsive. So when you mix impulsive with thoughtless and also he's... oh, what was the word, I had a saying for this kind of thing. Oh, here's the combination: It's shameless and relentless. And the combination of that put together is just a soup of disaster that you're brewing on that stove.
So he scares you more than the idea of a Ted Cruz presidency, for example?
Well, Ted Cruz—you know what you're getting. You know exactly what he's going to try and do. He’s ideological and partisan, and you understand it. But when Donald Trump starts talking about nuclear weapons, I don't know what's going to happen. Are we suddenly going to go to war with North Korea? Are you kidding me? Over what? Because now you’re—I—what—I can't even finish the sentence, because it's so hard to imagine, and he's so random. It's hard; he's unpredictable, which makes him dangerous, I think. Where Ted Cruz is predictable, so you know...
Let me say this, when the Koch brothers aren't for you, because they think you're unpredictable, there's a problem. [Laughs.]
One of the things that's interesting about this election cycle is how many news-satire shows we currently have on-air. Do you think that’s helping or hurting the conversation around the election?
I don't know. It's a good question and it's hard for me to tell. I mean, I think people probably watch those shows because they either maybe already agree with them, or they like the personality behind it. That type of thing. And I mean, some people watch late night [comedy] because they don't want to hear that stuff, they just want to escape from it, you know. But it's hard to know how much influence — again, it’s tough.
When Jon [Stewart] was doing it, he was really the only one who was doing that type of thing for a long time. And I think a lot of young people learned a lot of stuff from Jon, because he was such an amazing deconstructor of things and ideas. Jon's genius was really synthesizing something into an idea, that you go fuck, how come I didn't think of that. And he's right! That's how you would react to his pieces.
He nailed down being the voice of reason.
Yeah, he was. But now I think it's kind of a more—the way television just is—an a la carte thing. We deal in the race/class/gender area a lot, so our show feels more like we're looking out for the underdog. Sometimes we don't cover things that's more general, or in the mainstream, just because of the nature of what we're doing. [John] Oliver, he's that hardcore journalism, story-type of approach, where he's going to really take you down that deep dive on an issue and you're really going to… you know, it's almost going to school. And Sam [Samantha Bee]'s just blowing up the joint. I love her approach. She's like no, motherfuckers, there's gonna be no survivors when I'm done. And that's a fun way to look at it, too.
Your lens—the race/class/gender lens—is so significant for this election.
Absolutely. I think so, too. It's probably now more than ever, with all the issues. Everything from trans bathrooms to—you know, Oklahoma basically just outlawed abortion, which no one's talking about. The whole Tamir Rice thing, where basically the family was paid off so the cops could not be found guilty, which is criminal on so many different levels. I mean there's so many things happening out there that aren't being talked because of the distraction of this election, which is amazing for me, too.
One of the things your show did so well when it came on the scene was bringing different experiences of race, and specifically different experiences of blackness, to the forefront. So many of the candidates have had to address Black Lives Matter, for example. The internet has made certain sub-conversations come to the forefront.
[This election] is unusual in that sense. You wonder what's going to happen. Is that going to be a permanent type of slippering off there or... who knows? [With the internet,] people don't need an institution to give them information. It's easier to just get the information. People can broadcast stories, that type of thing, through their Facebook feed. Just with the whole sharing, you become aware of things. And in the same way, things can also be rendered irrelevant, because it's over-shared. We've seen it already. It's kind of a ying-yang in that.
It's a delicate balance you're working with.
Yes, exactly. And that people have already joked about, too. Because now on the internet and Twitter and everything else, people can get to the jokes first, before you can even get on the air that day! [Laughs.]
So how do you manage it?
[Sighs.] A lot of it, you just have to ignore. You just have to do your own thing, and have your point of view about things, and that's what you make the show out of.
The traditional approach to this stuff is: okay, what is the funniest joke about this? That's the traditional late night approach. And that's certainly a valid way to do it, even now. But the problem is, you're going to be competing with a lot of people who are going to be doing that, so there's going to be a lot of overlap. Because there are only a finite number of perfect jokes for something. [Laughs.] It sounds like a technical treaty, but it's kind of true. There's certain takes on certain things that are just the shortest way to the truth on it, right? To the joke.
So, if you don't want to compete on that field, now you have to compete with opinion. What is your personal opinion of this? Or, what is your further opinion of it? which is something that Jon started to do. Not just his initial opinion, but what's his further opinion. How is this just the starting point of a bigger thing that we should really be talking about? And so when you make your show about that—it would be really unusual for somebody to be doing that same thing.
Watch Larry Wilmore at the White House Correspondents’ Dinner on Saturday, April 30, or catch him on Comedy Central, weeknights at 11:30 p.m.
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