Lewis Black talks Red Sox, Filene’s Basement, and ranting to Boston one last time

Retiring from touring, the irascible 'Daily Show' veteran plays two final shows in Boston this weekend.

On our recent call, Lewis Black rants about the Yankees. (“The evil empire.”)

Rants to me about Boston weather. (“It sucks.”)

About a laundry list of current events and political issues.

But he raves about Filene’s Basement.

I ask what he’ll do in Boston this weekend — he’s here for two shows at the Wilbur Sept. 28 and 29.

“I just like wandering around the city. I think it’s pretty. I used to go to Filene’s Basement, that was one of the great joys of my life,” he says, then pausing, as if in reverie.

“Just hunting for bargains?” I ask.

“Yeah. When I was broke, I’d come up to Boston, work a show, then go see if there were any shirts on sale,” he deadpans.

At home, the real Black really isn’t a ranter, he tells me. (“Who would want to live with that? And I mean myself living with it.”)

But like Larry David, Black has cultivated a beloved grumpy public persona. Embittered complaints are his bread and butter, whether he’s shouting about politics on “The Daily Show,” screaming as the voice of Anger in Pixar’s “Inside Out” and “Inside Out 2,” or ranting about, well, anything, on his podcast, “RantCast.”

While those rants will continue, Black, 76, is retiring from touring after some 35 years on the road. He says goodbye to Boston this weekend: “Goodbye Yeller Brick Road, The Final Tour” plays two shows at Boston’s Wilbur Theatre Sept. 28 and Sept. 29.

Boston fans, catch him now. We don’t even have Filene’s Basement to lure him back anymore.

Meanwhile on Instagram, the ranting (thankfully) rages on: Whether he’s calling out AI-written articles or delivering reader-submitted rants about anything from cornhole to obnoxiously trendy restaurants. (“The ketchup has f— cinnamon in it! What the actual f—?! … There was no non-cinnamon option!”)

I called Black this week to talk playwriting, the Red Sox, the Emmys, his version of “Our Town” (amazing) and what’s bugging him now.

Boston.com: So why retire from touring?

Lewis Black: I’ve got other things I want to do — writing a play, writing a book. And touring has become harder to do. I’m a comic born in the industrial age, and we’re now in the technological age. I’m not great at the social media. I’ve got people who help me, but I don’t know how it works. I’m not in that ballpark. I achieved my popularity through television. And we’ve moved on from that.

I would have [retired earlier] if there was no pandemic. I needed to wander around, play some places I wanted to say goodbye to. Also it’s time for me to actually enjoy my life. [laughs]

These are your last two Boston shows ever. Will you have any specific Boston jokes you’ll open with?

I mean, I’ve played Boston so much, I wouldn’t even know what the joke would be at this point. [laughs] I started playing at [Cambridge’s] Catch a Rising Star almost 40 years ago.

How many times have you played Boston?

Hundreds. I did a show called “Media Muck” at the A.R.T. written by Chris Durang. We did four or five shows a week, afterwards I’d perform at Catch a Rising Star. But name a theater there, I played it: Emerson, Shubert Theater.

And does anything annoy you about Boston for a rant?

Your weather sucks. You people seem to think you have the same weather as New York. When I worked [Boston gigs] and yelled about the weather, people would go, “Oh no, it’s the same in New York today!” I’d take a newspaper and show them. I’d have to point out to them that, no, it’s not the same. It’s sunny there today, and this is your fifth straight day of rain.

[laughs] You think Boston weather is worse than New York in general?

New York weather kind of sucks as all weather generally sucks on the East Coast from January to March. But when I was working [Boston] from January to April, there were, like, four days when it didn’t rain.

What about Boston sports? Any take on that?

I’m a Baltimore Orioles fan. The Orioles were awful for a while, and because I hate the Yankees so much, I’d root for Boston. I did that for a while, but not anymore. Now, as far as I’m concerned, I don’t like [the Sox]. But I’ll always not like the Yankees more.

Good enough. Anything else that annoys you about New England in general?

No, I like it because you people are more bitter than I am.

[laughs] Your first night here is sold-out. Do you find you have a big fanbase here because we’re so bitter?

Yes, I think that helps.

Your last special, “Tragically, I Need You,” was for YouTube last year. Will you be taping another special?

I’m moving toward that, yeah. Anytime I’m on the road I’m working on the next special. Unless they don’t allow me to do specials after the next election.

[laughs] What are some topics you’ll hit at the Wilbur?

Well, it depends. Because now there’s so much stuff happening that you can’t really — I mean, last week, I literally did 15 minutes on what had occurred over the last five days. That was before I got to my act. Starting with Puff Adder, Puff Diddy, whatever he wants to call himself.

[laughs] You’ve been on “The Daily Show” since Craig Kilborn hosted.

Yeah, the show just got an Emmy, and I’m waiting to get mine.

Were you part of the team that just won?

No, because it’s given to the host, so since I’ve only been on it 29 years it doesn’t count.

[laughs]

It’s unbelievable. They call it “Variety Special” or whatever the name of it is. Well, no, it really just goes to the host. Why don’t you call it “The Host.” Why fool me?

[laughs] So how do you plan your topics for the Daily Show? Or do they give them to you?

That’s done in-house. They basically deal with what’s on the show that night. They tell me a [topic], which is fine. They write it out, we toss it around, work on it. During rehearsal, I throw some things in ad-lib— some are good, some are bad — and we keep going, and then we rewrite, and then it’s done.

Any recent favorite recent bits?

I love this last one about influencers, because it falls right into something that I haven’t yelled about on stage but that appalls me: how somebody becomes an influencer. You might as well call them influenzas. It’s based on nothing. It’s based on: eyeball. It’s based on: They would’ve been really popular in high school. What?

[laughs] True. You also have your “RantCast” podcast. I love the segment, “The Rant is Due,” which is fan-submitted. What are a few random things someone’s been upset by?

One of my first favorites was: “Why are you putting a pickle on my plate?” It was spectacular. It was a diatribe against pickles. Then people wrote back: “Pickles are the greatest thing that God’s ever given us!” It’s incredible.

[laughs] Classic. What’s another that’s generated debate?

Peanut butter: Crunchy or smooth? And roundabouts: love ’em or hate ’em?

Are you for or against roundabouts?

I don’t really care because I stopped driving.

One reader submission was on boneless chicken wings.

That was pretty good. [laughs] You can call them boneless even though they have bones. It’s perfect.

The RantCast will keep going, even when you retire from touring.

Yes. And I’m going to try to write a book. I’m going to try to write a play.

You went to Yale for playwriting. You’ve written 40 plays.

To the interest of no one.

[laughs] Any that people might know?

No. Nobody knows them.

[laughs] OK.

I had a comedy I tried to get done in Boston. “One Slight Hitch.” It’s been done in Williamstown, Massachusetts. It’s been done around the world in [small] theaters.

But never in Boston.

I just sent it up there, and they went: “No.” That’s generally what happens.

[laughs] So what’s the play you want to work on?

I’ve got a comedy that’s my version of “Our Town.”

That’s awesome. And you’ll write a book?

Yeah. [I might work on] a fictional book about living in New York and doing theater in the early ’80s. Or, the University of North Carolina at Chapel Hill took all my stuff — they’ve got three books, tons and tons of my papers. I want to go through ’em. I think there’s another book in there.

Right, UNC has your archives. Can people go look at them?

Yeah.

So you haven’t been through them?

They took them just before the f—g pandemic. I tried to go down, and they’d closed the library. I went back, and they’d closed the library. I’ll be going back in the spring, finally. That’s the other reason I’m retiring: to go do this. I’d like to see what the f— I wrote.

[laughs] You also do voice work. “Inside Out 2” just posted to Disney+. How did 2015’s “Inside Out” come to you? They must have had you in mind.

They did. They were writing it for me. They basically said to Disney when they were pitching the first one: “Imagine Lewis Black as the voice of anger.” Then they created that cartoon character for me.

Do you find it funny that people associate you with anger?

I really don’t think of myself as a ranter. But apparently it makes it easy for people to grasp. That becomes the PR end of it, which is always kind of goofy.

Do you have more voice work lined up?

I would hope that you’d write: “Lewis Black should have more work.” That would help.

[laughs] You’re signed to “The Daily Show” for the next two years. Would you ever retire from that?

I would. I have to see. I mean, I said I’d retire from stand-up at 65.

Anything you wanted to add for Boston fans?

I’m letting it rip. I mean, what are they going to do? Tell me I’m done? I’m done! They can’t fire me. I fired myself.

Lewis Black plays Saturday and Sunday night at the Wilbur, after a stop on Friday at New Hampshire’s Hampton Beach Casino Ballroom. Interview has been condensed and edited.

Lauren Daley is a freelance writer. She can be reached at [email protected]. She tweets @laurendaley1, and Instagrams at @laurendaley1. Read more stories on Facebook here.