It’s been less than two months since Larry Wilmore signed off for the last time on The Nightly Show and the “exhaustion” of being a late-night host is just starting to wear off.
Since Comedy Central prematurely canceled his show — leaving a gaping hole in not only their nightly schedule but also a vital dialogue about race, gender and class that Wilmore and his team provided during this election season — the comedian has returned full-time to his previous role as a creator, producer and writer of scripted television.
This weekend, his latest project will have its official premiere on HBO. Wilmore co-created Insecure with comedian Issa Rae (look out for The Daily Beast’s profile of her tomorrow), using her popular web series Awkward Black Girl as inspiration. In Insecure, Rae plays a character also named Issa, who is trying to navigate life as a young black woman in Los Angeles. She is unlike nearly anyone else on television right now, which is partly why Wilmore jumped at the chance to help bring her story to the screen.
Calling The Daily Beast the morning after the show’s Los Angeles premiere, Wilmore was eager to talk about the process of working with Rae and watching the show finally start to enter the culture. “To see it in front of an audience in all its glory on the big screen after having written it a while ago was so satisfying,” he says. Wilmore also discussed what life has been like after The Nightly Show and how he’s feeling about the 2016 election heading into Sunday night’s second presidential debate.
Below is an edited and condensed version of our conversation.
The first episode of Insecure went up early on HBO GO so a lot of people have gotten to see it. What kind of feedback have you been getting so far?
People seem to really like it a lot. I think, part of the thing that attracted me to working with Issa in the first place, is that quality that people are liking about the show. It seems like she’s somebody you’ve known forever. And people seem to relate to her very easily.
When were you first introduced to Issa Rae and what were your first impressions of her as a performer?
I was very impressed. She had set up the project at HBO and they were looking to pair her with somebody and we had the same management. They told me about her and I didn’t know about her. Then I watched Awkward Black Girl and was smitten immediately. There was just something about her. She was just so funny and understated and yet so alive at the same time. I just thought, whoa, this person seems really interesting. And then when I met her, you just fall in love in a different way. She’s such an interesting, smart person. We really hit it off, chemistry-wise.
How do you characterize your role on the show?
Well, besides co-creating it with Issa, in the first season I was basically just a consultant because I was doing my own show at the time. I was a little bit busy doing that. So I was kind of like the voice from afar, just giving advice here and there, helping out on some script direction when it was needed and that type of thing. But for the most part, the team — [executive producer and director] Melina [Matsoukas] and Issa — really guided that ship and really did a great job.
In the pilot, we see how Issa deals with being the only person of color at her job. Is that something you’ve experienced?
[Laughs] It’s something I experience every day of my life. Yeah, I think many black people have experienced that, especially if you go to certain schools or certain situations. Definitely, many, many, many, many times.
What did you bring from your own experience to those conversations?
Well, for us, it was really trying to figure out what this show was going to be about, what we wanted to dramatize. And there was something about that age, late-20s, where you’re trying to figure things out. Trying to find your place in the world.
Well any time you have more, you have to say it’s better. I certainly can’t say it’s worse. I could say it’s worse because there’s no more Nightly Show. [Laughs] No, you know, I like to use the word encouraging. When I see show’s like Donald’s — I love Atlanta, it’s so cool to see that type of world. And Aziz’s show [Master of None] on Netflix is so interesting to me too. I’m a big fan of Jill Soloway [Transparent] and the storytelling that she does. I think with all these different types of storytelling, it’s not really a black and white thing, it’s just point of view. It just makes everybody raise their game, which is nice.
Yeah, I mean that really came through at the Emmys this year, especially compared to what we’ve seen at the Oscars. Is that gratifying in any way for you to see that?
Absolutely. I loved seeing Alan Yang and Aziz [Ansari] win that writing Emmy. It’s one of the hardest ones to win. The speech he gave was great where he’s encouraging other Asian-Americans to get out there and write, you guys, get in the pipeline. All of that stuff is encouraging, because, like I said, it encourages all of us, people who are writers and creators to keep inventing, pushing forward more points of view.
I’m sure you miss The Nightly Show, but have there been any positives in not having to comment on the news four nights a week?
Yeah, you’re not as exhausted, that’s for sure. It can be depressing when you’re in that world all the time, because there’s so many negative stories. I really like creating shows and that sort of thing, so I’m getting back into that. It’s something that I do honestly love to do. But I do miss the world of being able to communicate directly with the audience. That’s a fun thing to do and it can be very powerful in certain situations. The grind of it I don’t miss, because it is a grind. nd it’s such a crazy political season as well so some of that stuff you do miss talking about for sure.
Is there anything specific that’s happened since your last show that made you want to have that platform back?
Wait, it’s the opposite! "Name something that isn’t something you could have talked about." It is the opposite question. There’s no one thing. Something’s happening every single day. Every day! And it’s shocking every time, like I can’t believe this is happening now.
Like Trump’s visit to the black church in Detroit? I feel like that’s something you guys would have had fun with.
Oh yeah, we would have had so much fun with that, all of those things. Even Hillary talking to Mary J. Blige, all of that stuff. I mean, you talk about awkward, there’s so much awkwardness happening. I’m looking forward to this weekend’s debate too, to see how that goes.
Any predictions for the second presidential debate?
I think Trump will probably do better in this one. It’s a more relaxed format. But we’ll see. This one is always kind of interesting, because it’s a town hall format. But he’s basically a salesman, that’s what he does, so I think when you’re talking directly to people, he might do better in it.
Probably not. It’s really not my thing to go after what comedians are doing. Because I always feel like we’re jesters at the end of the day. I’d rather go after the people who are the guardians or what we’re doing — the news people and the politicians and that sort of thing. I always feel like those should be my targets, not really entertainers. That’s just my personal opinion.
But do you worry about moments like that, whether it’s the Fallon appearance or Saturday Night Live, legitimizing Trump in a dangerous way?
I worry that he won the Republican nomination, not based on his appearance on SNL, but based on the primaries and the political system. That’s more worrisome to me than any comedy show he’s been on. I think the Republican establishment is as concerned. The big takeaway is how that’s come about and manifested itself, how this creature could have done that. We cannot blame his success on his appearances on Fallon and Saturday Night Live. If that were the case, my God, the strategy for becoming president would change dramatically.
So if you had a talk show, whether it’s The Nightly Show or something else, and Trump came to you and said he wanted to be on your show, would you say yes?
Oh, absolutely. But I would have my own style of how I would handle it. It would be how I handle it, completely different.
There seems to be some growing concern that African-Americans won’t come out for Hillary as strongly as they did for Obama. Is there anything she can do at this point to change that?
She could change her middle name to Hussein? No, look, no candidate will get what Obama got, because he had an historic candidacy. So it’s a false comparison. No one’s going to get that. It has nothing to do with Hillary, it’s just impossible. He was the first black president. Some people that probably never voted came out to vote for Obama for that. But she’ll get enough to win. I don’t think she has to worry about getting the majority of the black vote. She’s only needs enough votes to win, she doesn’t have to match Obama to beat Trump. She only needs to beat Trump.
So are you feeling pretty confident about her chances at this point in the game?
Absolutely not! Are you kidding me? There’s way too much time left in this election. So many things can happen. There’s such a history of elections swinging at the last minute. Look what happened to McCain [in 2008]. The economy collapsed and he was doing pretty well at a certain time. If you look at the history of candidacies, many of them have changed in the last weeks, where people have gotten momentum. So anything can happen at this point.