This week, The Gist, the daily news and culture podcast I host for Slate, turned 5 years old. To celebrate, my producers and I put out a special week of programming that culminated in this conversation with comedian and veteran writer-producer Larry Wilmore.
Wilmore is the co-creator of HBO’s Insecure and Grown-ish (the spinoff of the hit ABC show Black-ish, a program that he was also an executive producer for) and the host of the podcast Black on the Air. He joined me at Slate’s Brooklyn studio to discuss comedy, politics, and cultural criticism. Read a lightly edited transcript of our conversation, or listen to the full thing via the audio player below. You can also find The Gist via Apple Podcasts, Overcast, Spotify, Stitcher, Google Play, or wherever you get your shows.
Mike Pesca: You started your podcast in 2017?
Larry Wilmore: Yeah. That was two years ago. Time flies.
What was different about—how were your expectations upended by the actual experience of doing the podcast?
Well, it’s funny. I wasn’t sure if I wanted to do a podcast or not. I really didn’t know. After The Nightly Show went down, first of all, [I was] exhausted from producing a television show every day. Bill Simmons called and he said, Hey man, would you like to do a podcast? We went out to lunch. We really talked about it. It was his actual belief in me to do it, which kind of sold me on it. I thought, well, this is something that I can do, and I can still manage the other things that I’m doing, and I can get out part of the expression that I had in the Nightly Show arena.
I thought it would be nice to have that expression, and I love interviewing people. I didn’t really get a chance to interview people much on The Nightly Show. It was always a discussion. My expectations were met, but that was fulfilled in a way that I hadn’t even imagined, because I realized that in the conversations themselves I would find my point of view. I would discover things about the person that I didn’t know, having an expectation going in and that sort of thing.
Let’s go to Insecure and Black-ish. Is it easier [now] to get a hearing, a consideration, as a producer? You are black, so you are going to be a producer of black content, because that’s who you are. Is that something that [the industry is] now desirous of, and before you had to knock on the door three extra times?
Well, I wouldn’t say I’m a producer of black content, but I like to be a producer of what I call content that isn’t on the air currently. For instance, I just produced a show with Jessica Gao, who is a Chinese American writer. It’s about her family. In my mind, this family isn’t on television. I’ve always pushed for, why can’t somebody like me just do any kind of content? I have a lot of different projects. I have a project based on my love of magic that I’m developing at Disney—
I love that.
—that has nothing to do with race or anything. That’s in its particular place, and I’ll do that. You should be able to say I suck for anything that I do [laughter]. I have pushed for the ability to suck in anything, Mike, rather than just racial content.
That will be the glorious day—
Believe me, I am succeeding one show at a time.
—where we could give you 1½ stars based on the content of your character.
Exactly. Correct. Not on the color of my skin.
It sounds like you have a lot of female co-creators on this stuff.
Yes. That’s another thing I’ve always been passionate about. Women have always had the shorter end of the stick in the writing and creating fields. I’ve always been supportive of that. I like working with young people and new voices and that kind of stuff. I’m kind of in that mentorship position. You get to a certain age, Mike, and if you can accept that gracefully, then it’s really a cool thing. I love collaboration. I love bringing my OG, old-school knowledge into something, and then you get the YG stuff in there too. The mix of that is fun. It’s really exciting.
I wanted to ask you about an interesting article I read. Wesley Morris wrote this article about him being a critic and being in favor of art for the morally right reasons, as opposed to the artistically right reasons. I loved it. Then, when I read it back, I realized the case in point that he was pointing to was Insecure, which happens to be your show. He felt impinged upon as a critic. When you read reviews or know what the consensus is, it’s inflected by the morality of the message.
Here’s the thing. Here’s what reviewers have always done, which I have not liked: They always review with their version of what they like to see. I’m like, motherfucker, this is the movie that I wrote. Review it for its merits. It just occurs in different ways.
In the ’60s, after Pauline Kael and the way that she reviewed movies, people started reviewing movies for how much they thought they should be going against society or going against established moviemaking. If they weren’t taking chances in that, they weren’t worthy. That was a Pauline Kael type of movie.
The new criticism—new is an important part of that.
Very correct. That’s how movies were judged from that. Now, you have “woke” criticism. Which, to me, is another imposition of the critic on the thing they’re reviewing, which, to me, doesn’t really belong in reviews. It belongs in an essay about something else.
His [article] sounds like more of a discussion-in-a-barbershop type of thing too. Or discussing it with friends. He was talking about the dilemma of not wanting to trash it amongst friends because he wants to seem loyal to it, which is different.
Right. He wasn’t saying that he, as a Pulitzer Prize–winning critic, couldn’t say or do whatever he wanted in the New York Times. He maybe wanted that dinner conversation to go a little more smoothly.
I don’t find that so much in media, to be honest with you. There may be a little bit of it. I found it more in politics with Obama. Black people did not like to hear criticism of Obama from black people. Tavis Smiley and Cornel West were almost excommunicated. They were in the Chappelle trade. Traded up. I don’t even know what team they made it on at this point.
They had to play two years in the Japanese League before coming back. Michael Eric Dyson, too, was another one.
Yes. I always tried to have my criticism with a sense of humor and everything, but I acknowledge that, as a fan, I’m allowed to criticize the Lakers, but I’m still a rabid Lakers fan. I know what that difference is.
The very thing that, perhaps, a critic like Dyson would say, something like selling out a part of your community, that’s the feature, not the bug. The fact that people, that white America, can identify with Barack Obama, that’s maybe one of the things that they were most critical of. The pandering to white America.
Sometimes, I intuited the opposite. I felt a lot of liberal white America pandered to Obama and treated him with too much preciousness. Like he’s some figure to not be messed with. We don’t know how long this fragile butterfly, this Negro butterfly, is going to be around. Let’s treat him well, with kid gloves. No, he’s the president. He’s a Chicago politician, for Christ’s sake. As comedians, we should be able to criticize power no matter who’s holding that power. I didn’t like when comedians wouldn’t have criticisms—that was the kind of criticisms that you should have for a president no matter who’s in office.
Sometimes it occurs differently when you agree with them, but it should still exist.
I do think this about Obama. He was not above criticism, but if you look at—and this is in great comedy—if you look at a lot of the comedy that’s been aimed at the presidents during my lifetime—Bush, Reagan, Clinton, Trump—personal foibles played a huge role. Obama really did take that off the table.
He did, and this is what I’m saying—this is the liberal preciousness to have him be perfect. To have him be the perfect messenger.
You don’t think he really gave comedians less fodder just in terms of personal failings?
No, they were just scared. I think people were scared. For instance, Obama took way too fucking long to make a point.
Yes, he did.
Way too long. Nobody made enough jokes about that. I did a joke, I remember, where I was like, if you just ask Obama what he had for breakfast, he’d say Well, this morning, there was some sort of decorative plate … just get to the point. I’m fucking hungry over here. Whereas, Bush would have just said eggs.
But it would have been French toast.
Nobody made enough fun of his foibles. Sometimes SNL did like him wearing mom jeans. That’s funny. That’s an arrow at something about him that we can laugh at. But what they instead did was: They made jokes about his being black, which isn’t a joke about him—it’s a joke about a bigger thing that they can find humor in, but not about him. There weren’t enough jokes about him. I think because people—it’s that preciousness, and people were just scared. [They felt] I don’t want to make fun of the black guy because black people are going to come after me. Which, even if that is the case, as a comedian, you got to take that heat. It’s like going after Beyoncé. You’ve got to be careful if you’re going to do it. You better bring it. It better be really funny because the Beyhive is going to come after you.
There’s no good way to do that.
No, there’s no good way. Arguably, it’s more dangerous to go after Beyoncé than Obama—Obama is only going to be in office, at the most, eight years.
It’s term-limited. There’s no constitutional prescription against Beyoncé … I like Key & Peele’s anger translator because that was getting at truth—
That’s about being black.
Well, that’s why I asked you about it. I think that does get to a truth.
It gets to a truth about blackness, not about Obama.
About the kind of blackness he had to represent.
But it’s a general point. It’s a funny point—I’m not saying it’s not funny, I’m not saying it’s not a good observation, but it’s not about him. The one that they did that was closer to being about him, but was still a general point, was how he changes up his handshakes because Obama did do that.
He code-switched his handshakes. I did not know that.
Yes. Now, code-switching is something that Obama does do. I mean, politicians do do that, but he does it in a funny way because of the handshake. That’s more about him. Once again, it’s comedy coming out of flattery of the person and not critique of the person, too.
Do you think that comedy, sarcasm, parody has been at all a check on the Trump administration? I loved your conversation with [Malcom] Gladwell about this. I think it has been an escape valve, and it has been a pressure-release valve, but has it done anything to keep the excesses of the administration in check?
My opinion on this is that it never does.
I think you may be right.
I don’t think it ever has. I don’t know an example where it has. I think maybe at the most there could be two examples where it could have hurt somebody. I would say [President] Gerald Ford. When SNL started making fun of him, he became a little more buffoonish than people had really seen him, and I think that hurt him against [President Jimmy] Carter, possibly. And I think Sarah Palin. When Tina Fey did her, I think people did view her as a little more buffoonish than they had before. I was at a convention when Sarah Palin was there, and it was amazing. She was a rock star. I was impressed. I was like, Man, you don’t even think of McCain. This is who the candidate is, really. She actually was the candidate. Had she not stumbled, McCain might have been elected. That star power was pretty bright.
I think Gladwell’s point was criticizing that portrayal for defanging her and making her seem more impotent or less dangerous.
I know. I disagree with him on that. I think he’s ascribing a purpose to comedy that isn’t there. That’s his projection of what he thinks comedy should be. Sorry, Gladwell, comedy is designed to make people laugh. All that extra stuff, good for you that you found that, but that’s not what it’s for. Nobody is in the writers’ room going, All right, guys. We’ve got to get this bill passed with this joke. I don’t know how this joke is going to get this bill passed. No one thinks like that.
I always say activists should engage in activism. I always feel like that’s why we have these words that are different. Comedy exists to be comic. I believe they serve different functions. Occasionally you have an outlier that does something different, but I don’t believe that usually is the purpose of it. It’s interesting, Mike. Whenever that is the purpose, the audience can kind of feel it—I always felt like the audience was like, “That’s trying to do too much.” You can always sense that. It’s usually the unintended consequence of something more than anything else, I think.