Roy Wood Jr. Talks About ‘Imperfect Messenger’ And Getting More Personal

Roy Wood Jr‘s Imperfect Messenger might be the funniest comedy special of the last year. In the hour (which just dropped on Paramount + after an initial debut on Comedy Central), Wood deals out hilarious truths about how much we really want to know when we ask how they’re doing, flags, white allies and merch, the Fast And Furious movies, and the pursuit of happiness before taking a hard turn at the end to talk about prison reform. It is, at once, of this moment and something that you’ll be able to re-watch in a couple of years without a major shift in relevancy; a balance that says a lot about the stagnation of progress in this country and even more about Wood’s skill as a comic.

In our recent chat with Wood, he talks about his desire to avoid putting out instantly dated material while also going deep on his coming pivot to more introspective comedy through a one-person show he’s in the early stages of developing. Ever busy, the comic/podcaster/Daily Show correspondent/actor/producer also tells us about challenging himself and “threading the needle of pain and laughter” while talking about how he plans on talking about modern issues without preaching in two upcoming TV shows that he’s producing.

I know you’ve got a couple of dates coming up in February. Are you planning on hitting the road?

Those are all COVID makeups. So I’m just honoring them because that’s stuff that’s been on the books and been hopscotched around for the past year and a half. But after that, I’m trying to really buckle down into writing some TV and movies. I’ve got some other projects I’m trying to do. This Roy’s Job Fair podcast I did last year, I’ve got some ideas on how to grow that. My next hour special is probably going to end up being a one-person show, anyway. You know, it’s going to be more introspective, so I need to go and mine the material first and then start working it out. I’ll still do sets around New York, but after February, it’s not really in the cards for me to be touring. But we’ll see… The shows may not go to series and then I got some extra time on my hands. But the plan is to just write and sell content as much as I can.

What led to this slight pivot toward more introspective material down the road?

I think there are only so many different ways you can scream about what’s happening in the world around us. I think I’ve done that successfully for three straight specials. So I’m more curious now about what’s going on with me and my family, and I think there’s a connection to fatherhood. None of this would’ve happened if I hadn’t have done Finding Your Roots last year. And for me the whole Finding Your Roots thing really informed me a lot about my family. And I think there’s a journey within that that ties to a bigger whole for all of us. You know, basically when you look at… As a people, we’re faster to pass down recipes than we are our traumas. You know?

I basically want to explore: are we better off or worse off when trauma is or isn’t passed down to us? Did your parents protect you or did they leave you misinformed and unprepared for how to face those same things yourself? And I think within that is something much more introspective and deeper than just the traditional Comedy Central hours that I’ve been doing. To really mine and really explore that, that’s six months, I think, just gathering intelligence and then another year of figuring out how to work it out because it’s not going to be a traditional club set. So where do you even build that? You know, I’ve been talking to Neal Brennan and Mike Birbiglia a little bit about it, because they’ve done that pretty well — Birbiglia for the last 15 years, but Neal in the last five — they both have very introspective internal battle oriented stuff that’s going on with them. Chris Rock did it a little in Tamborine when he started talking about divorce and porn. That’s a huge deviation. The people who didn’t come up on Chris Rock. Chris Rock’s never talked about himself in that regard. So that degree of emotional nakedness… I just found that to be very, very interesting.

Is it frightening to go into that space? And is that part of it also? The idea that you want to scare yourself at this point in your career and really push yourself?

Yeah. Because otherwise what am I doing? So there’s a lot of stuff that I did. There is a lot of shit I got to process first as a human being and then turn around and figure out… To be re-informed about the relationship with your father… You know, to have a relationship with a dead person be re-imagined 20 years after their death, that’s wild. And then concurrently figuring out how that informs me about the kind of father that I want to be for my own son… So I think there are some elements of fatherhood in there, because a lot of us, we’re like first-generation successes in our families. A lot of African Americans are. And so you’re trying to be something for your child that you never had yourself.

In a way, there’s part of it being a father and then other parts of it are performing the position of father. To set a new example. I had a conversation with Baron Vaughn. He said it perfectly. He just said that we’re the curse breakers. People of this generation of African-Americans have the wherewithal to know what we’re going through and some of the tools to figure out ways to get through it while also raising people. It’s not an indictment of past generations because they just had to survive. They just had to get through the day. No mental health awareness day in the sixties for Black people. You just went to a fish fry on Saturday. You just went to a block party. You just found one day to decompress, but without knowing the full intention of it all. I think that’s part of the issue.

Obviously a very different experience, but like my grandparents were in concentration camps and [from what I was told] never talked about it. Everything was just buried, buried, buried. But sometimes I wonder if that’s part of it too. If it’s not just protecting so much as it’s just like you took the pain and you hid it away and you tried to move past it.

Well, and it’s tough because that’s your story and your trauma and you don’t have to share it with anybody. You get to cope the way you want to cope. But there has to be some acknowledgment that, what are the ripple effects of making that choice? What are the ripple effects of that? What do you do when you’ve been re-informed and how do you go forward with that? So I just think this theme of fatherhood and family trauma and what do we do now? Like now that we have the information and some of the tools, okay, well what now?

This [new direction] feels highly relatable and timeless. This current special, Imperfect Messenger, feels really timeless. Is that the [unifying] goal?

You can have a special that is of the moment, like of that year. I wanted to try and do one that was of this decade or this five years. You can do one that’s… If you do it right, you can do one that’s of the generation, you know, of this generation. I don’t want to be as specific to people. That’s the part of why I don’t really mention people in my specials, specifically politicians and shit like that. I try not to name a specific event, but more the tone. I don’t need to quote a specific police incident to have a joke about police reform. You know what it is, and that’s an issue that’s going to be around for a little while longer. The people change, the issues stay the same. So if you can talk to the issues, most issues are generational. There’s still a need for prison reform. So that’s going to be around for a while. So I think in that regard, it is intentional to a degree, but I just don’t know how far out I can de-age the special or anything. It’s just this idea of where we are as people right now and what is happiness? What does that look like? What does just trying to feel good look like? And how does that manifest itself? To me, that’s the throughline.

Is there anything upcoming that’s bringing you back into the documentary space after producing The Neutral Ground?

Yeah. So, CJ Hunt… I’m in bed with him about something else that he has coming up. I’m not at liberty to say what it is yet because it’s not public. But for now, what I enjoy in general, especially in TV, is having shows that kind of address problems. And so the probation officers show at Comedy Central didn’t go. But we sold a show to NBC that I’m executive producing about a black woman doctor coming home to take care of her family care clinic. And when you look at the healthcare crisis in this country, it’s not at the hospital level, it’s at the street level at the clinics. And that’s where you really see a lot of the odd day-to-day drama that a lot of people go through. And you make it funny and make it light and there’s still a way to have comedy that lives adjacent to real-world shit that people are going through.

That’s why we created this National Guard show that I sold to Fox. On the surface, it’s a workplace comedy. But when you really look at the National Guard, outside of weather events, the National Guard’s only function in life is to show up and fix government dysfunction. Most of the things that they’re coming to fix and take part of are things that could have been taken care of if there were better politicians in place in those particular places. And so I think that there’s a way to live adjacent to a lot of the different issues that are out there without being as on the nose as we were at The Daily Show. Because at the end of the day, if it doesn’t make you laugh, you did not achieve the goal as a sitcom or as a comedian.

So, I’m not trying to preach to people, but I think there’s a way to do things that kind of sit in that same pocket. So, to the whole point about a documentary, there’s an idea or two, but right now until this thing with CJ and I really comes to fruition, I’m just going to stand pat with the two TV shows. And I have a movie idea that I think could do something else in terms of living adjacent to some of the stuff. But it’s just, it’s fun right now to really look at horrible shit and figure out how can I make this funny and get people to laugh at it. I enjoy threading the needle of pain and laughter. If you do it right, I don’t know, it just feels more rewarding. It feels more cool. I don’t have the solutions. I don’t think that any single joke or any single TV show is going to fix all of this stuff. But if it helps someone else just take a breath and get through it, then I think it accomplishes its goal.

‘Imperfect Messenger’ is available to stream on Paramount +