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Roy Wood Jr. Won’t Stop Pushing Stand-up Forward

Roy Wood Jr. Photo-Illustration: Vulture; Photo by Andrew Lipovsky/NBC/NBCU Photobank

I was talking to a stand-up the other day, and Roy Wood Jr. came up. Almost in unison, we both said, “Best comedian working.” Taken together, Wood’s three Comedy Central specials — 2017’s Father Figure, 2019’s No One Loves You, and 2021’s Imperfect Messenger — are a testament to how good stand-up can be: the originality, the thoughtfulness, the tireless search for the best possible punch line. Watching Wood perform and hearing him talk about his stand-up, it’s hard not to be struck by his clear-eyed sense of purpose. He knows why he does comedy, what he wants his comedy to do, and what he wants from comedy. For as great as he is right now, it’s maybe even more exciting where he’ll go next.

On Vulture’s Good One podcast, Wood discusses his new special, taking on difficult subjects, and his hopes for the next stage of his career. Below, you can read an excerpt from the transcript or listen to the full episode. Tune in to Good One every Thursday on Apple Podcasts, Spotify, Stitcher, Overcast, or wherever you get your podcasts.

Good One

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On His Bit About Black British Actors in American Civil-Rights Movies

This is a serious issue of contention in the Black community, so I felt like I had an opportunity with this bit to at least explore and add commentary and perspective to the conversation. The idea of that joke was birthed from a real conversation. I like juggling dynamite of who’s already arguing about something and then figuring out ways into that. This is an issue that really isn’t commonly known outside of the Black community; it’s a pretty inherently Black joke that I think you can still get even if you’re not Black.

And I think, If I’m not going to talk about it, who is? If I don’t say it, I don’t know who else is going to say it. There’s only a handful of comedians that would even dare to explore it. It is family business to a degree: this idea that a lot of the issues around Blackness and issues between Black people — conversations white people and non-Black people shouldn’t be privy to or shouldn’t have an opinion on. And I think you can make the argument about not having an opinion, but you want to know what we’re talking about, and that’s fine. Because I do think that it helps to create more dialogue around the issue, which is what needs to happen. If that’s constantly happening behind closed doors, it’s not helping anything, in my opinion.

What I landed on was if I don’t know your pain, I can’t trust you to portray my pain on-camera because then you seem like an outsider and an opportunist. And the truth is the only reason we don’t know anything about Black Brits and their pain is because the American history books don’t fucking teach your shit about foreign racism. They’re just now talking about Tulsa.

Now I did this show at City Winery, and I got checked. That’s why I love running bits in front of my friends and non-comedians — because my non-comedian friends tend to give me far better criticism. They stress test the premise. My comedian friends give me punch lines. So in the early days when I was developing the Black Brits story, I was told that it skewed a little too pro-British, in that I was presenting this argument for Black Brits being in these films, and honestly it did not bother me. What my friend said (and this is an actor who has been on set with Black British actors in some of these films) was — he talked about how some of them sometimes are disrespectful on set to American Black actors. That’s not to say that Black American actors aren’t disrespectful, but it is especially stinging when it comes from an outsider. So that’s where that line in the bit came from: “As long as Black Brits know that they’re coming into a system that benefits them more than it does to people who are already here.” That was something that gave me a little more perspective in balancing the argument.

Now if I had had another year to work the bit, you can figure out a funny scenario or whatever with that, but what I’ve learned over these three-hour specials is that if you cannot support a point with a joke, you have to make that point in a sentence, or two sentences or less, and hurry up and get to a joke. All of this preaching, TED Talk shit? Save that for the one-man show.

On Figuring Out the Complicated Closer of Imperfect Messenger

It’s literally ten minutes cut down from 14. That story and the whole run about prison reform has so many emotional valleys, and it gets a little dark. What I realized was there was a problem with the way I sequenced the order of material. A story that dark being that close to the end of the show, we’re like, “No, we have to move this up.” You need seven minutes minimum to land this plane, preferably ten. So you need to move the sad story up a little bit in your act. Well, now you get into the sad story sooner, which means you’ve got to fucking rat-a-tat-tat-tat going into this story. So it resulted in a reordering of some of the material in front of it as well. And this is two weeks before, going back and forth with my director.

What’s wild is I’ve known my director since 2005, when I was doing morning radio. He was a promotions assistant, and he was the guy that would come in and just crack jokes off-mic between breaks and eventually worked his way up to being the head writer of my morning show once I was hosting. So if there’s anybody who knows my humor, it’s him, in some weird, pre-stand-up Neal Brennan–to–my–Chappelle–type shit. He’s seen and watched me for years and years. And he was just like, “You need more time because the people are still processing that story. And then you’re saying, ‘Thank you. Good night.’ It’s like, What?” Because it’s either that or just close on the story. But then that’s a left turn, and that’s not fair. They came to have a good time and kick it. You can’t just take a shit down their throat at the end.

On His Concerns With Stand-up and Hopes for His Future Comedy

I hope comedians don’t get locked into public reactions to their material. I’m going to be honest, man. Like, I hope all this Chappelle shit doesn’t create a bunch of comics who are just counterculture for the sake of pissing people off instead of actually talking about the shit that’s important to them. There’s a little bit of that in stand-up now. It’s cute, but it’s not sustainable. That’s not a sustainable creative process: to just be contrarian for the sake of outrage because, “Oh, you’re a bunch of crybabies, so watch me fucking attack every one of your norms just for the sake of, Oh, no, he didn’t.” But at what purpose? What are we trying to accomplish in the long run?

My journey right after this — the Comedy Central trilogy — I think the journey for me is inward. It’s about my own feelings and fears. The more topical, opinionated stuff that stylistically I’ve done the last five years, that’s stuff that’ll be the quick hits for YouTube. I’ll self-produce and just put out and keep the water wet. Maybe I can sneak on late night and get away with something a little edgy that might be fun. But as far as the actual next hour show, if I’m going off just the things that I’m interested in right now, it is my relationship with my father and that fucking family in Georgia who used to own my people and what they’re up to now. I’m not going to go fight them or nothing, but if they own a business, I might go leave a bad Yelp review.

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In his special, Wood tells a story about his attempt to get his former neighbor out of prison 20 years into a sentence for driving the getaway car in an attempted robbery turned murder of a fixture of the Birmingham community. Earlier this year, Wood was on an episode of Finding Your Roots, in which he learned a great deal about his family’s history in the U.S. This included the history of how the name Wood came from the slavers who originally owned his ancestors.
Roy Wood Jr. Won’t Stop Pushing Stand-up Forward