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.”