Jeremy Siegel: You're listening to Morning Edition. In 2018, Roy Wood Jr. Took a trip to Boston for a Daily Show segment.

Roy Wood Jr.: How racist is Boston? For decades, people have called Boston racist for numerous reasons. The Red Sox were the last baseball team to integrate. Bostonians violently resisted desegregation. Even in 2017, fans at Fenway Park called Adam Jones the N-word.

Siegel: The piece dug into staggering statistics of inequity — but was also hard not to laugh at, exemplifying Wood's combination of comedy and social commentary that landed him the job of hosting the White House Correspondents Dinner last year.

Wood: I'm well aware that not everybody in this room knows who I am, so let's just address the elephant in the room. I know what it is. Half this room thinks I'm Kenan Thompson. Other half think I'm Louis Armstrong. President Biden thinks I'm the daddy on 'Family Matters.'

Siegel: In October, Wood stepped down from The Daily Show after eight years to focus on his standup. I sat down with him to talk about his career, how he was influenced by his father, who was a celebrated civil rights journalist, and yes, the city of Boston. You're going to be doing stand up here in Boston, a city that you're not unfamiliar with. You did a sketch for The Daily Show that a lot of people, I'm sure, have seen, asking the question, Is Boston a racist city?

Wood: How do you measure racism?

Akilah Johnson [previous recording]: Well, you do it in a variety —

Wood: How many times the N-word is said in a day? Like a Negro-meter?

Akilah Johnson [previous recording]: No.

Wood: Like a Negrometer?

Akilah Johnson [previous recording]: No.

Siegel: What is it like coming to Boston?

Wood: I have a good time in Boston. The thing that was important to me about that Boston piece was talking to locals.

Unnamed woman 1 [previous recording]: I don't see that racism myself. Honestly.

Unnamed man [previous recording]: No, I don't think Boston's a racist city.

Unnamed woman 2 [previous recording]: I think that we've got a lot of, like, attention with, with our sports being in the media.

Wood: So Boston's racist reputation is a conspiracy formed by people who hate Boston sports teams for winning all the damn time.

Unnamed woman 2 [previous recording]: Yes. They love to hate us.

Wood: And ultimately, that piece was just about perceptions and how we perceive society based on the experiences we've had in that society up until that point. And so, you know, we went around and we spoke to some people on this side of town and spoke to some people on that side of town. There are some blatant problems.

Unnamed woman 3 [previous recording]: A white person walked into a room in Boston. I want to think about that. I'm the only white person here.

Unnamed woman 4 [previous recording]: Know your neighborhood. Know where you are allowed, know where you are wanted.

Wood: You know, that was an interesting thing to figure out: Well, why do you think Boston has that perception, you know, in terms of discrimination and everything. And then you get into everything that's happened. You know, as I understand it, Boston's mayor wanted to have a 'coloreds-only Christmas party.' I don't think that's how it was branded. But would you look at that?

Siegel: Mayor Michelle Wu, yeah, having a Christmas party for elected officials of color, a tradition that dates back a few years.

Wood: Yeah, no white elected officials, all the other elected officials, you know, can come. And then of course, everything would with Dr. Claudine Gay and everything over at Harvard. And so like there's always these things that are just, hmm, that's peculiar that it happened there. But does that mean this is a thing? But, you know, anytime I've come to Boston, you know, I've always had a great time. I've been playing The Wilbur for probably, you know, 6 or 7 years now. And it's been great audiences. So, you know. But as a traveler, I'm very leery to equate the worth of a city to me coming visiting for a couple of days. I think that's not fair. Like someone goes, 'I went to Boston and somebody was mean to me one time at Applebee's. That city is terrible.' Wait a minute. Let's get the opinions of the locals. So that's what we were trying to accomplish with that piece for Daily Show. Because, you know, I come from Alabama and there's a lot of opinions about Alabama from people who ain't from Alabama. But if you talk to people in Alabama, it's a differing perspective. It's like, yes, there are these things and there is these systems in place that make me feel like the odds are not in my favor to be successful. But also, here are some good things about this place. And so, you know, I was trying to just extend Bostonians the same courtesy to be able to speak to those other things.

Siegel: Well, that's something about your role in The Daily Show, what you did on The Daily Show: Actually talking to people in a place. And I'm curious, having done that, having experienced so many different levels of talking about politics, about culture, about the comedy behind it all, what do you think is missing from political coverage in the way we discuss it?

Wood: Nuance. I think nuance has left us as a society. There are no conversations with nuance anymore.

Siegel: You tweeted what many people thought was a brilliant idea recently: The tiny desk debate, playing off of NPR's Tiny Desk Concert. Tell me about this idea. Because I love it. I love it.

Wood: That would be — Listen, we want everything. Debate culture in this country is already an issue that I don't — and not in a good way. But there's something intimate and small about the Tiny Desk Concerts that makes us want to watch artists that you don't even really care about because you're seeing them in this different, intimate setting. Also, it is impossible to be a fake person at 10 o'clock in the morning. Like, they record Tiny Desk in the morning, like early afternoon. The sun is out, so there's less lying. I don't know, I don't know what it is about Tiny Desk, but I think you see people for who they genuinely are. And if it's worked for music, then put two politicians. Like, you know how when two kids cut up and you force them to sit side by side, you tie them together with a string or whatever, put them in the same T-shirt or whatever? That's what we should start doing with our politicians, at least for debate.

Siegel: I'm imagining politicians in the same T-shirt now.

Wood: Yeah, and it shouldn't just be Tiny Desk debates. They should be like, have a debate in the back of a fast food spot. Like get around the regular people who are actually going to be voting for you. You shouldn't only have to answer questions from Americans in nice sweaters.

Siegel: Your father was a major figure in media, was a broadcast journalist. Did it ever feel weird going into the same career in a way, as your father, but making jokes, doing satirical news?

Wood: It didn't really feel weird until I started having real opinions. You gotta remember I started standup when I was 19. It wasn't until my mid 30s that I really started becoming a guy that like, really went, what's going on with racism? Let's look at mass shootings and see how the death of customer service relates to people feeling more alone and contributes to feelings of loneliness and actually makes us think that everyone is disposable. How can I take these two weird things and connect them and try and make that funny? That journey didn't start until well into my 30s, and I feel like I did enough as a comedian. You know, I will never be what my father was for this country. I would never be as poignant or have as much depth. I think that humor helps people to understand, but you could only go so far with humor, because eventually you're getting closer to the nerve endings of America, and then it stops being funny.

Siegel: Roy Wood Jr. performs on Friday night at The Wilbur. You're listening to GBH News.

In 2018, comedian Roy Wood Jr. took a trip to Boston for a Daily Show segment titled “How Racist Is Boston?”

The piece dug into staggering statistics of inequity — but was also hard not to laugh at, exemplifying Wood's combination of comedy and social commentary that landed him the job of hosting the White House Correspondents Dinner last year.

In October, Wood stepped down from "The Daily Show" after eight years to focus on his standup. He’s bringing his latest show, “Imperfect Messenger,” to The Wilbur Theater on Friday.

“I have a good time in Boston,” he told GBH’s Morning Edition. “The thing that was important to me about that Boston piece was talking to locals. And ultimately, that piece was just about perceptions and how we perceive society based on the experiences we've had in that society up until that point.”

He wanted to know: Why do people think Boston has that reputation?

“There's always these things that are just, hmm, that's peculiar that it happened there. But does that mean this is a thing?” he said. “As a traveler, I'm very leery to equate the worth of a city to me coming visiting for a couple of days. I think that's not fair. Like someone goes, 'I went to Boston and somebody was mean to me one time at Applebee's. That city is terrible.' Wait a minute. Let's get the opinions of the locals.”

Wood, who grew up in Alabama, said he often encounters people with strong opinions about his own home state.

“There's a lot of opinions about Alabama from people who ain't from Alabama. But if you talk to people in Alabama, it's a differing perspective,” he said. “It's like, yes, there are these things and there is these systems in place that make me feel like the odds are not in my favor to be successful. But also, here are some good things about this place. And so, you know, I was trying to just extend Bostonians the same courtesy to be able to speak to those other things.”

His father, Roy Wood Sr., was a civil rights journalist and media pioneer. Wood said he can delve into serious topics, but he doesn’t try to fill his father’s shoes. He started doing standup at 19, and didn’t start looking at topics like racism or mass shootings or loneliness until his 30s.

“I feel like I did enough as a comedian,” he said. “I will never be what my father was for this country. I would never be as poignant or have as much depth. I think that humor helps people to understand, but you could only go so far with humor, because eventually you're getting closer to the nerve endings of America, and then it stops being funny.”

When he looks at the state of political discourse today, he said, he wishes there was more nuance.

“I think nuance has left us as a society. There are no conversations with nuance anymore,” he said.

He has recently proposed an idea for improving America’s political landscape, especially around election seasons: Tiny Desk Political Debates, modeled after NPR’s Tiny Desk Concerts.

“There's something intimate and small about the Tiny Desk Concerts that makes us want to watch artists that you don't even really care about because you're seeing them in this different, intimate setting,” he said. “Also, it is impossible to be a fake person at 10 o'clock in the morning. Like, they record Tiny Desk in the morning, like early afternoon. The sun is out, so there's less lying.”

It could bring a bit more candor to the scene, he said.

“I don't know what it is about Tiny Desk, but I think you see people for who they genuinely are. And if it's worked for music, then put two politicians,” he said. “Like, you know how when two kids cut up and you force them to sit side by side, you tie them together with a string or whatever, put them in the same T-shirt or whatever? That's what we should start doing with our politicians, at least for debate.”

And there’s no need to stop there, he said.

“They should be like, have a debate in the back of a fast food spot,” Wood said. “Like, get around the regular people who are actually going to be voting for you. You shouldn't only have to answer questions from Americans in nice sweaters.”