Larry Wilmore on the Challenges of Breaking Into Late Night and Why He Teases John Oliver

The 'Nightly Show' host also discusses the importance of finding his show's unique take on the news.
Larry Wilmore of 'The Nightly Show'

[The Hollywood Reporter spoke with an assortment of the biggest names in late night about changes to the volatile variety talk category at the upcoming Emmys for a magazine story. Some longer Q&As from those interviews are going online.]

In a late night TV world characterized by outrage and incredulity at current events, it's possible that no host is as frequently and profanely incredulous as Larry Wilmore, or at least as profane as The Night Show can be on Comedy Central.

"Yeah, we probably should be more of a premium cable show with as much cursing as we do," Wilmore laughs.

The Nightly Show premiered in January 2015 with the difficult task of replacing Comedy Central's Colbert Report, and Wilmore is candid about the learning curve the show has had when it comes to its approach to the news and the panel discussions that have become its most distinctive feature. Wilmore also knows that he is far from the only fresh face in late night who has faced high expectations and similar challenges of self-definition in the past 18 months.

Speaking with The Hollywood Reporter, Wilmore offers his perspective on the changing standards and expectations faced by both The Nightly Show and the competition, which isn't exactly "competition" anymore, and the event that helped shape his show's distinctive voice.

The late night field has gone through such an overhaul in the past year. Does it strike you as funny that you only really had a couple weeks or months as the new kid on the block in this terrain?

I know. It wasn't long, that's for sure. It went by pretty fast. Yes, so much happened. When I learned that I was taking over, which was now two years ago, that's how fast time flies, Stephen was still doing his show. He still had six more months to do his show. There was no thought that Jon [Stewart] would be leaving, for goodness' sake, and that was going to happen nine months after that, which nobody saw coming. No one had even heard of Trevor [Noah], you know? No one knew Samantha [Bee] was going to do her show. The thought of Letterman not being around anymore? Fallon had just started his show in 2014, right? Fallon was the new kid on the block actually. I mean, man, now that I think about it, good lord. A lot has happened. I mean, that's not a lot of time. Two years, right?

It is, and suddenly you have almost seniority in this field.

Exactly, exactly. Right. That's insane, but now Conan looks like Johnny Carson in terms of his tenure. Conan has been on what, 21 years now?

In total service, something like that. What does it feel like being in the middle of that kind of sea change? Do you notice it as you're in the middle of it, or is it just like you're noticing it now as you think about it from the outside?

I think now that I think about it, I'm like, "F—," you know? I think it is kind of interesting, because I guess that means we're at the start of something, right? Of a new way of "This is happening." I think the biggest effect is there's so much of it that people are consuming it in different ways. It used to be very simple, a matter of ratings, and people either showed up to watch somebody at that time or not. But now people watch on their phones, they see it on Facebook, they see clips on Twitter, so there's completely different ways. People are making up their own shows. They might watch a little of this person's show, a little bit of that person's show, see like 19 minutes of John Oliver's takedown. Get a little bit here, a little there. Start with Conan's monologue. I mean, who knows? There's so many ways you can watch these things now. It's not the way it used to be.

Okay, for that hypothetical person who is making up a Frankenstein late night show, what would you tell them that they should be watching from your show?

Watch The Nightly Show. All of it. I'm going to be selfish. I'm going to say watch all of my show. We do a little different thing in each act, but I actually think it's a good thing. I think this type of thing is good for what we do. It keeps us on our toes. You have to stay alert. You've got to keep raising your game. When I see somebody killing it, I'm like, "Come on, guys. Let's keep going." I think it's good. I call it healthy competition, really. I think it's really good. As a consumer, it's got to be great because, if you get bored with something, you can go to the other thing real quick. Then you might get bored with that and go back to the other thing. I think there are some people who are your dedicated watchers who are going to watch everything, which is great, but I think there are more and more a la carte people. In fact, someone told me that. They said, "Larry, I love watching the first part of your show, and then I'll switch over to Stephen and watch his show." I'm like, "Wait! No, don't switch over," but I understand. They want to experience both of those things.

Do you personally have any time to watch anything late night at all?

No. I really don't have much time. Occasionally, I'll catch a clip the way that I'm talking about. I'll be on Facebook or something and I'll see somebody's thing. I'll see like a little bit of it, and I can appreciate it like that. It's just time-wise, it's just difficult, you know?

Trust me, you're not the only one. When there are this many people starting out and sort of experimenting with the format and trying to make their mark, do you think that encourages people to try new things, or do you think it discourages innovation because people don't want to fall flat on their face out of the box?

I don't know. I guess it depends on who it is, I suppose, right? I mean, it's different for different things. I think if you look at The Daily Show, like Trevor probably had the most unenviable position because he had to follow Jon Stewart, and he has a pre-existing show. If you look at somebody like Sam Bee, she got to create her own thing without any expectations that there was a show there. That was probably liberating for them. They're like, "I don't care. We'll do whatever the f— we want. Nobody knows that this is yet," so that's got to be liberating in some senses.

Our show was odd because we weren't doing Stephen's show, but we were in his time slot, so there was an expectation, and Jon was still on the air, so we were following The Daily Show, so we kind of had the mix of both of those. Yeah, we could do our own thing, but there was an expectation of something also. Then Colbert's is odd. Colbert had the weirdest one of all because he had to follow in the expectation of his fake self. He had to live up to his fake self in some way, and follow David Letterman, so Stephen had the most challenging one. I don't know if people appreciate how challenging Stephen's job really was.

How have you responded to the need or desire to change and adapt and evolve your show when you're in the middle of this job, which is really a speeding locomotive that you guys all have to be working on?

Right. I've been in television a long time, as you know. To me, that's just part of how television works. Whenever I did sitcoms, that always happened on your show. Once the show was on the air, it takes on a life of its own. It develops and it becomes something else. That's just how you make a show, so that part you always know is going to happen when you're doing television. It's just a natural part of doing a television show, and it should be. It's rare that you have something exactly the way it should be immediately. Even Jon, when he started The Daily Show, it took him a couple years to really make it his version of it.

Where would you say you are in terms of the journey of making your show yours?

I think we're in a really good place right now. It took a while because there was an original idea that Jon had, there was an idea that the network had, there was an idea that I had. Making all those work, and then once it gets on the air, what actually works. Plus, we didn't want to be The Daily Show because that already existed. We had to be something different. There were all those factors into making it. It didn't just exist in a vacuum, but then, like I said, once it's on, you find out what works, what doesn't work, and you try to hone that in and just make it more of the best out of the things that work. You say, "Okay, this works. Let's do more of this. This doesn't work. Let's do less of that."

Along those lines, obviously your panel segment is not the only panel discussion in the space because Bill Maher does it, et cetera, but it's one of the differentiating factors of the show. When you have something like that that you know is at least distinctive, how much do you concentrate on making that part sort of sing every night?

Let me give you a little background first. The original idea that Jon had for the show was that it was completely a panel show. That was his original concept, but we just felt that was very difficult to do right out of the box, and we thought it was important to have a comic segment on the show where you could get a sense of my voice comedically laying in on the events of the day. It was something that the network thought was important, so that was the first little tweak, but that was very much part of the DNA of the show in the beginning. That was the part that was the hardest to make evolve and work.

If you look at our early shows, we were booking four people on the show every night. That was very exhausting, you know? When I think of Bill Maher's show, he had three people on once a week. Try four every single night, and to have a topic that's good for those four people. It was very exhausting, and the amount of time that we had to have a real discussion was too limiting. We couldn't service that properly, we felt. It would have even been difficult if the whole show was just that, but at least it would have more of a chance to be something, right?

We realized early on that we couldn't really service a panel like that, and it felt a little too newsy and not enough comic-y, I think, for the network because of the nature of the type of people we were inviting. Then we realized, "Look, we have a group of comic performers here who are interesting. Let's make that the basis of our panel, and just invite in a guest to kind of talk to our family." That way it's easier. We have one person. We can focus on them as the guest, and we can discuss a panel in a more comic and intelligent way. A combination of the two. It doesn't put so much pressure on that part of the show to be a full-blown talk show, because it isn't that.

From your point of view, what has been the process of finding the right guest to be that extra person in the discussion? Because there are some episodes where the person gives and takes every bit as much, and then there are some episodes where the guest says very little, honestly.

That's a great question, because it is one of the more challenging things that we try to get better and better at. Okay, so the way that you book people on TV shows is usually they have a movie to promote or a book to promote, and they have a certain type of interview speech, let's call it, that they give on all of their shows, right?

Our show is different. We're inviting someone on who can speak about a particular topic and can be engaging and get into a discussion. Maybe they're fiery or whatever, so it's a different skill set. You're looking for an interesting person with a point of view more than just a celebrity who is promoting something. Partly. And also we wanted to do that because we can't compete with Jimmy Fallon and Stephen and have those A-list stars. We just can't compete in that world, so why even try?

Another one of the original concepts from Jon Stewart was that he wanted the show to be a platform for people you don't get to see all the time. To find new voices out there, and so we try to do that on the show too. We have this young lady named Quinta Brunson, she's on BuzzFeed, she's a comic, and she's fantastic. I never even heard of her. She has an opinion. She's smart. She's funny. It's the type of skill set that we like. Somebody who is informative and entertaining at the same time. They have something to say. They have an opinion, and they can mix it up.

Sometimes we have comedians, people who are just fun people. We find them interesting and we know we can throw any topic at them and they can handle it. Sometimes we have more of an expert. We don't have as many what you would call dry experts now because the nature of the show, they're kind of all by themselves, but then it depends. Sometimes there is that person who can be interesting, or we would have Neil DeGrasse Tyson or Bill Nye, just a larger-than-life expert in a thing. It's actually fun finding the people who can fit in that role, because it's not your normal type of guest that would be on another show. I think it's liberating for them.

We've had a lot of rappers on too, which is kind of funny. They love coming on and feeling like they don't have to perform. They're not on to do a song like they would on another show, but there's a, "Wow, somebody really wants my opinion." They actually love that they can come on and just talk. They're kind of funny characters anyway. That always gets a kind of funny energy in the room, which makes it kind of electric.

From the outside, I think we all kind of assume that this election cycle has been comedy gold, but has it been a great challenge to keep coming up with new ways to laugh about the absurdity?

Yes, absolutely. Yeah, it really is, because like, in the example of Donald Trump, he's such a caricature in many ways that the stuff that he says, it's hard to write anything that's more outrageous than what he's actually doing. I thought Sarah Palin was the ultimate expression of comic outrageousness in a person. In fact, even Tina Fey, all she did was just say exactly what Sarah Palin said, and it was still the funniest thing she's done, right? Trump gives you that kind of challenge, but it's still a challenge that's a fun challenge. To take on and all those things. It's not like an impossible thing. It's actually fun to come up with the things.

How aware are you at all times that if Trump says something stupid, or if Hilary makes a flub, there are ten people with basically the same job as you getting ready to make the same jokes?

Yeah. For us, we have to go a little further or deeper to find our particular angle of why are we talking about him? We call it "What is our Nightly take on it?" so we're not just doing the same joke. If we're going further, what are we really talking about here? What is the purpose of me presenting this to my audience? Was there another angle that we haven't seen or something like that? Because right, then you're competing and just doing the same kind of reflective joke and the sound bite, you know?

Sure. Knowing that everybody is doing the election thing, how close an eye do you keep on making sure that every night you guys are covering things that you know nobody else is possibly going to be covering?

Not too much. You can't really chase that too much. You just have to have your own take on things. We're still connected to The Daily Show in some ways, and if they're real heavy in a topic, we'll go, "Let's not cover that, because they're doing their whole show on that. Let's do something else." Sometimes we'll do that, but sometimes we'll do the same thing, the same topic, but we'll know that our take is a little different. We'll just continue with it, but that's the only show that we'll think about just because we're connected to it in some ways.

I would say that you probably have the most bleeped swearing of any show in this space. Is that something that you guys take pride in?

I think it's probably our rebellious nature or something. Where we say we're keeping it "a hundred," it's that type of thing. Yeah, we probably should be more of a premium cable show with as much cursing as we do. I'm always thinking, "Why? Larry, you didn't have to say it like that. Why did you do that?" It's kind of funny. I kind of laugh at it. I don't know if we take pride in it. I think some of it, after the fact, we realize we probably didn't' have to use all of that language, you know?

Do you feel like the show's voice has been to some degree shaped by the chaos of this election season, and is there any way to change the voice after we get out of the election?

It's possible, but I think our voice started being shaped by the Baltimore riots last year and some of the racial stuff that was happening. I went out and talked to these gang members in a diner, and that kind of was the first time we felt like we have a kind of a purpose here that's a little more than just doing what The Daily Show is doing, whose purpose always was politics and Congress and all that kind of stuff.

Then the election just kind of heightened it in a different way, but the election is going to go away soon. We have to know that our show is kind of a show out there looking at the underdog. We're the ones not afraid to talk about race, class and gender, these issues and all those types of things. The election is a way that presents these issues in a different way, but we know those issues are still there when the election goes away. We know there's still going to be people trying to silence people in different ways and they type of stuff. These issues that we care about are still going to be out there. In other words, Cosby, his trial is going to be going on for a while, so there you go.

You talked about people watching in bits and pieces, a la carte. Now certain shows like Fallon, like Corden, have made viral clips a cottage industry and the basis for the show, and that's not so much what you guys do, but who is keeping an eye on that, and how much is that in the back of your minds? 

It is, to a certain extent. I don't know if we have an actual watchdog on it, but we know that it's good to share things like that. I know we had Neil DeGrasse Tyson on the show where he did this kind of a mic drop thing, and that was a fun viral thing that went there, but our show, you're right. It's not designed to have the type of things that Fallon and Corden do, like the karaoke type of thing or lip sync battle and those types of things because those are such pure comic things. Ours is so much more specific and has different structure to it, so it does get shared, but it's just a different tone. I guess that's the best way to say it.

Looking at the other people who compete in the Emmy category that you're in, you've got competition that airs only one night a week. You've got people who are on premium cable who have no content limitations. You've got people who have an hour per show. From your point of view, what are the advantages and disadvantages of being a half hour, being nightly, and on Comedy Central?

I don't know what the advantages or disadvantages would be, but with things like the Emmys, you just don't know. There's no rhyme or reason, you know? I think if people have an awareness of your show and they like it and they want to acknowledge it, then that kind of thing happens, but it's tough to say.

Just format wise, when you look at what, say for example, John Oliver gets to do, and you look at what Sam gets to do with only one night per week...

Oh yeah. F— those guys. F— Sam and John is all I have to say. (Laughs) John Oliver, I've teased him so much about his schedule. It's so funny, but yeah. There's pros and cons of doing those. I think they feel frustration, probably, because they don't get a chance to comment on everything. There are things that go by that they probably say, "Oh man, I wish we could talk about that," but then on the other hand, they get to distill what they're saying over a week's time and put it all in one show. There's pros and cons to that. We feel the opposite. We have to do a show every night, so we have to react very quickly. We don't have the time to necessarily do that type of thing, but we get to weigh in right away when something happens, which is nice too. There's pros and cons to both.