Roy Wood Jr. on Why Comedians Are Imperfect Messengers and How the Pandemic Changed Comedy Specials

On Friday, comedian Roy Wood Jr. joined fellow Daily Show with Trevor Noah correspondent Ronny Chieng in L.A. for the “Heroes of the Freedomsurrection” monument installment. Dubbed a tribute to the “heroes” (think Tucker Carlson, Ted Cruz and Donald Trump) responsible for inciting the Jan. 6 riots, the installation — up all weekend at Westfield Century City mall — is the kind of knife-in-your-side comedy Wood says he wasn’t doing before joining the series.

But since debuting on the late-night, satirical news show in 2015, the comedian — who has already released two one-hour specials and had roles in Only Murders in the Building and the upcoming Confess, Fletch — has seen his style shift. Yes, he can still be fun and light, but Wood also says he’s less afraid to get into heavy topics and is more adept at giving his audience space to process what they’re feeling.

That personal creative shift also comes at an interesting time not just for the comedian, but for comedy in general. The title of Wood’s third special, Imperfect Messenger, references his own experiences “screwing up” on issues he cares about. But it also speaks to how comedians as both performers and people are not “oracles of all of society’s ills” and, thus, are not “without mistakes,” according to Wood.

Screwing up in comedy can be a matter of both audience and artist perspective, but as the pandemic ramped up the turnaround time for specials — sometimes wrapping editing weeks instead of months from when they were shot — “screwing up” in our rapidly changing social media and news cycles may have larger implications for the art and artist than before.

Ahead of the “Heroes of the Freedomsurrection” event, The Hollywood Reporter spoke to Wood, 43, about how The Daily Show and the rapidly changing news cycle has reshaped his comedic style, why he wanted to do his second special live (but didn’t) and what makes working on scripted shows like Only Murders in the Building a “hell of a lot easier” than his stand-up or correspondence work.

Your second special’s title Imperfect Messenger speaks to the content of your set, but also seemingly to comedy and the role of the comedian. Did you mean for it to and if so, why are comedians imperfect messengers to you? 

I don’t know who did it first — the comedian or the audience — but somewhere along the way, somebody decided comedians were the oracles of all of society’s ills. No, we’re wrong a lot too. This entire life is just everybody contributing ideas, but they’re not all going to be the best ideas. So for me, I know that I have ideas on what I think can make the world a better place, but I also know that I’m not gonna sit here and act like I’m without mistakes or haven’t done or said idiotic things. Which was part of trying to indict myself near the back end of the special with regards to prison reform and trying to get my friend out of prison without first seeking the permission of the victim’s family that he was convicted of killing. Even in myself, I am as woke and righteous and I want to do the right thing, but then here I am also screwing up. So it is more about me, but the title does in a way — few people have caught that. It is a nod to me but also a nod to the occupation of comedian.

The special topically felt less evergreen than your first, Father Figure. How concerned were you, in light of how fast the news cycle and social media move especially with some of those more sensitive subjects, that it might become outdated? 

We taped that special, and it aired 13 days later. The normal turn time for a comedy special pre-pandemic was anywhere from five months to a year. You’ll shoot it and then you’ll put together all the promo stuff. Then you’ll put together all of the clips that you want to do. So the set was developed, I’d say from February through October. I just felt like because the news cycle is sped up because you don’t know when the next tragedy is coming around the corner to throw off the new cycle, it has to be reflective of the times we’re in now. I think that’s the new normal for stand-up. Stand-up comedy can no longer be — you can’t shoot a stand-up special and put it on the shelf for six months while you decide where it slots into your fall schedule. You have to put it up immediately. There’s a lot of stuff that Netflix is putting out this summer that was just shot last month in L.A.

I chose to do two weeks because I’m at a disadvantage. I’ll say that. I’ll be honest. I released one of the few hour specials that is still coming on traditional broadcast cable and not a streamer. So I had to be cognizant of Comedy Central’s full schedule online and what I’m up against. I knew I needed most of the year to work on the special, but October was really the only time to air it because once you get into the middle of November you’re into holiday programming for the most part. On top of that, I have to come up with a special that resonates for 60 minutes, 52 minutes and 44 minutes. And that’s a part that was a little more difficult in how you stack the show and the topics that you want to broach. You can’t take a commercial break in the middle of a police reform line, especially when certain bits are tied to the other bits. Continuing with commercials as to how it relates to how to edit a special — I’m good at it now because I’ve done it three times. But I have envied that a lot of my peers are able to just drop an hour and the hour just lives.

Did having to think about all of that impact your turnaround speed at all? 

Those types of logistical hurdles were also part of what played into just doing something that we flipped as quickly as possible. Because if I had shot that special in October and waited until February, we would have had a new president, and there would have been a whole different field with COVID. If you’re not careful with comedy now, and you sit on the jokes too long, you look like the guy who just hasn’t caught up. You look like the AOL email address and it’s not your fault. It is what it is. But I think that’s the future of stand-up. It’s just putting it out fresh. If you want to know the truth, I wanted to do it live. Sinbad did something like that for ABC years ago and it never left my mind. That’s still something that I want to do — live with commercial breaks. That’s insanity, but that’s fun and I think that you have to add a degree of difficulty to it because you’re trying to get eyeballs. So I wanted to do this special live-live and for whatever the cost which, based on the face Comedy Central made, I assume would have been expensive. So the middle ground was a two-week turn. That had never been done at the network before. We looked at a lot of other specials just from that same stretch last year and they were all on one or two-month edits as well. Everything is shortening. The runway from shoot to polish to air has to get shorter because people just move on.

You’ve got a very specific style in Imperfect Messenger for delivering the joke with information tucked inside, and I think the Black Brits conversation is a really good encapsulation of it. I’m curious how you might describe your earlier style and in what way you feel like it might have evolved by this third special? 

The style used to be a heavy joke, light joke and the light joke could just be something random. In Father Figure there was a run about Black music and how Black music is the litmus test for the mood of the Black community and what the Black community is going to do. The next joke was about cruise ship captains and airline pilots waving goodbye to you when you get off the vessel. There was no social commentary on that other than just me not wanting people to speak to me in public. (Laughs.) That was the spine of that bit — when people are polite to you, it adds more time to your day. Then the next joke after that is about white employees inside of civil rights museums — and you’re right back into struggle and pain-land. Whereas now, I think I’ve gotten more comfortable in not couching bits. When I started talking about the Titanic in my first special — it’s your first special and you’re supposed to love it, but I go back and watch it now and am like, “Why am I wasting time talking about chicken nuggets in a fast-food restaurant?” There’s so many other things I could have been unearthing. So what I figured out as I’ve evolved was that you can have lighter and heavier sections within a heavy topic. The oscillation is the same.

I also try to stay on topic because I don’t want to preach to the audience. I’m not here to beat you over the head. The only thing I’m trying to do is if the issue is A and B, I want us to consider C. With the Black Brits, the issue is Black Brits are stealing roles from African Americans and African Americans are going, “I hate Black Brits.” The Roy approach to the joke is: How much does the lack of knowing each other’s struggle play into the lack of respect? Because we measure respect through struggle. You have to have jokes that support that thesis, so that gives you places to digress and be a little silly and then come back to the spine of it, which to me is that a big byproduct of hatred across the Black diaspora is the lack of education about one another’s struggle. I don’t have an opinion one way or the other on Idris Elba playing whoever the hell, but that’s the digression — when you find out that your favorite Black actor is British. That’s the captain and Titanic shit, then you come back to the history lesson. That joke, in particular though, I went back and forth about even doing because that’s family business in a way. That’s not a conversation that I’m completely sure white people in the mainstream need to be privy to, and even if they’re privy to it, I don’t know if they need to have an opinion on it. So I’m not going to unearth the history of it because this isn’t the place for you to have that. I’m not here to build that up.

The way you just described your style sounds a lot like how comedy on The Daily Show, which to some degree could be considered explainer journalism, works. Is it fair to say that environment has shaped or reshaped how you think about your comedy or even the subjects you cover? 

The Daily Show gave me the weapon of how to slickly slide a knife in when the audience isn’t looking. If you go online and watch some of my old Conan sets, it gets into race but it’s fun, it’s light. It’s not heavy. I’ve always had those thoughts. I’ve always had those inclinations. I just never quite knew how to put it together on stage. I think that’s also an unfortunate byproduct of starting comedy too young. I started when I was 19 and sometimes, if you’re not careful as a performer, you can pick up a lot of bad writing habits, a lot of bad performance styles that keep you employed, but don’t elevate your ideologies. The show 1,000 percent helped that, but what it also helped me develop was an eye for being able to do heavy topics.

What I noticed that Trevor [Noah] did — and I’ll be honest in saying that I stole this from him — if something’s heavy, slow down. Let it sit. So much of my comedy is up-tempo, it’s frantic. For this special, I slowed down a lot. A thing that I think happened in 2020 is that people became more in touch with their feelings. Comedy that makes you feel something, positive or negative, to me is more effective and is just as important as comedy that makes you laugh. That is a joke I’m more interested in telling. My comedy is not escapist. There’s comedians that are out to solve it, but I’m here to talk about it. We’re not going to solve it. Trevor gives the audience time to process their feelings, and I think we have to give that to audiences now.

Between your specials, The Daily Show and your appearance on the first season of Only Murders in the Building, you’re living in three different realms of comedy right now. So how is your approach to something like Only Murders different than the Daily Show or stand-up?

To me, the scripted stuff is so much more fun, because the jokes have already been found. It’s just a matter of which way do you want to tell this joke. After that, it’s a matter of figuring out what you are doing in the scene against Steve [Martin] and Martin [Short]. Steve was great. Martin was great. They were kind. They work fast. You definitely need to know what you’re doing on set with them. They don’t waste time. But the difference in the three disciplines is that I’m lesser and lesser of a priority in each. Stand-up, I control my destiny. I get to do whatever I want, when I want. Daily Show, I can do what I want, but it has to be within these guardrails. Generally, it’s just me out as a correspondent. Trevor’s there, but he’s there to just throw you the alley-oop. On a set for a scripted show, you are not the star. You are a visitor. So it is your job to throw alley-oop to Steve and Martin.

By doing that, you also shine and the jokes easily come through. I think that’s probably the biggest thing that I enjoy because it’s the least amount of pressure. I just did Confess, Fletch with Jon Hamm, and my character has jokes but Jon Hamm is the engine in the scene. That’s a hell of a lot easier than going out to a rally and talking to Trump supporters. (Laughs.) It also helps to have great scene partners that want you to shine. You can end up on shows sometimes and it’s not the best experience because they don’t want you to be funny. Which I don’t understand. Your face is on the poster. You’re gonna get all the glory. I’ve been very blessed though through the years. Tiffany Haddish was great to me on The Last O.G. Rhea Seehorn was great to me on [Better Call] Saul. You’re dropping into part of an institution, so you also don’t want to mess it up. I’m more nervous in those situations because I’m coming into something that someone else created and I want to make sure that I honor it. Whereas the Daily Show and stand-up, if it’s not funny, it’s my fault and I’m the only one disappointed.

You and fellow Daily Show correspondent Jaboukie Young-White both appeared in Only Murders. Did you know that you both were going to be in it? 

No! (Laughs.) We didn’t even find out until after the fact. We did a gig together recently and riding back from Connecticut we talked about the experience and it was spot-on. I really enjoy being around Jaboukie. I couldn’t have imagined achieving what Jaboukie’s done at the same mile marker. I wasn’t mature enough. I wouldn’t have been able to handle it. But I learned a ton from him and Jessica Williams. Jessica Williams really gave me a proper primer in how to do correspondence as a Black person in her time on the Daily Show before she left.

Interview edited for length and clarity.