After more than 30 years of hitting the road hard year after year, Lewis Black is closing in on his final curtain call as a full-time touring comedian. But that doesn’t mean he’s run out of stuff to say. It just means he’s going to find different ways to say it.
As he brings his Goodbye Yeller Brick Road tour back to The Wilbur starting Saturday (September 28) for one last weekend-long victory lap in the city, Black brings with him another slate of material that, while largely curated and sculpted right on stage from night to night as he’s done for years, is as solid at its foundation of social satire and an artistic approach to the use of the “fuck” word as ever. But aside from the show itself, a reflection on the long and winding road that has brought Black through Boston year after year since before the Clinton administration has the multi-faceted comedian feeling retrospective in all the right ways as he prepares to scream obscenities into that good night.
Just as we’ve had the pleasure of doing plenty of times in years past, Vanyaland recently got Black on the phone again for a spirited conversation on the state of the country, the state of comedy as he prepares to pass the torch to the next generation of performers, what he’s looking forward to most in retirement, and just how special the city of Boston has been for the wildly successful, relatable irate, and colorfully-tongued jokeslinger.
Check it out.
Vanyaland: Hey, Lewis! How’s it going? It’s great to reconnect wit you.
Lewis Black: Every day is a joy, Jason. I woke up today, and the news is just filled with stories of how we’re really going to work together as people. Did you know we rank 23rd in happiness as a country? I mean, c’mon.
That means we’re the greatest, if you look at it in perspective to Michael Jordan, right?
Oh yeah, definitely. [laughs]
We’ve chatted a few times over the years, but this time feels like an all-time special moment to chat with you again. We have the Goodbye Yeller Brick Road tour coming to Boston one last time for shows at The Wilbur over the weekend. After so many years of coming to Boston, what’s the outlook on making your way to town one last time?
I mean, I’ll come back to visit, but I’ve always loved playing in Boston. It really was such a pivotal place in my growth as a comic, where To Catch a Rising Star in Cambridge was one of the great clubs in the United States, and you could only name, like, five at that point in time. So to be able to work it as a headliner was incredible, but to watch the other comics come in and do it was also something special.
Something else that helped me out as a comic, as much as anything else was when I was cast in a Chris Durang play [as Morton Hell in Media Amok, 1992] at Hasty Pudding [Theater] for the American Repertory Theater. We only did the show maybe four or five times a week, and even then, it wasn’t a long show, so I could walk off stage, go over two blocks and work at Catch. I got to know a number of comics that performed there very well, and I learned a ton from them. It was one of the clubs that I really got to hang out at and watch some of the best I’ve ever seen.
I can’t imagine the feeling of being in a room like that, and feeling like you’re seeing superstars in the making, or even feeling like you are getting there yourself. It’s cool to hear how integral Boston was for you early on.
On the other end of the spectrum, I played Nick’s [Comedy Stop], and when I played there, which I only did once or twice, all I did was walk on stage and the crowd was already yelling “Fuck you!” and I knew to expect that, but after I played there, I said that I would have really enjoyed myself just as much if I was in a room full of bears and I was throwing meat at them to make sure they didn’t eat me.
Looking back on that experience now, with these shows at a place as legendary as The Wilbur on the horizon, what’s the feeling as you make your way toward the finish line of your touring days with this particular collection of material to offer?
It’s great, but I wish I played The Wilbur more. I had some problems there that we won’t get into [laughs] but something else I wanted to touch on was how big of an effect it was on me to be able to help in whatever way I could with the idea of starting a Boston Comedy Festival, which I really believed in. It was important, and it wasn’t majorly commercial when my friend Jim McCue was trying to put it together.
But I’ve played all over Boston. I’ve played at the Emerson, the Wang, the Shubert, and a bunch of other places, and I love all of those places, but The Wilbur is just really special. It’s a hugely special venue, and I’m pissed that I didn’t play there more. I was trying to prove a point by shoving a pen in my eye, basically. [laughs]
Well, now you have the chance to make it even more special with a big tip of the cap. Now, obviously, years out on the road can take a toll on you, but what was the catalyst in making the decision that this was going to be your last ride?
If there had been no pandemic, I would have been retired by what became the end of the pandemic, because there were things I wanted to do. I wanted to go and do some stuff down at the University of North Carolina, my alma mater, I wanted to spend more time down there, I wanted spend more time enjoying myself and having fun, and writing. I wanted to write another book, and I wanted to write another play. I also wanted to do two more stand-up specials, which I did wind up doing, but they weren’t the ones I had planned on doing.
What occurred to us is that, you turn a corner and get back out on the road, and you’re discovering that first, people are either not coming out as much, and secondly, way more people are out touring now, so the routing started making it so I was competing with other people, after traveling in the bus for so long, and not having to compete with people. Something else I began to realize too, was that people just kind of expected me to show up every year and a half, so if you missed me once, you’ll see me next time, and I realized that was coming to an end. I had to tell people that this was it, that this was telling them “happy trails, and we’ll see you down the road.”
That’s totally understandable. Especially since it doesn’t really feel like a goodbye if you still plan on doing things in a creative space. It’s more of a “see you later,” no?
Yes.
In that spirit then, will coming off the road help in not only freeing up physical time to do more stuff, but also, the creative energy to get those projects moving?
I think it will give me the time and space to do that, and I won’t have to worry. It’s another thing when ten or twenty years ago, or even just before the pandemic, when you stopped touring, it was like if an athlete runs the 440, but then stops for four years, or even two years, it’s going to show. The last time I performed [before the pandemic] was literally the night before the shutdowns, and the next time I got on stage was 500 days later. So you definitely lose that kind of stamina, especially as I’ve grown older.
That makes you realize that you don’t have the kind of juice to do what you had been doing, where it was stand-up and the other stuff I wanted to do, so something had to give. I mean, I’ll get back up on stage occasionally because I’ll drive myself fucking nuts if I’m just sitting around in front of a desk all day and watching what’s going on in the world. But I really do just want to sit down and write, and see what comes out.
At that point, what would take precedence? More writing in the sense of putting a book together, or more playwright projects?
I want to do both, but there are two plays that I’d like to work on. One of them is to turn my book, I’m Dreaming of a Black Christmas into a one-person show, and then I’d also like to get back into writing my version of Our Town, and I don’t know where that goes, but I started writing that one a long time ago and a I really want to go back to it.
As for the book, I don’t know what that will be yet. Before the pandemic, I had a book, with notes and everything, but the pandemic kind of threw that idea out the window, because I was the kind of person who believed that if aliens were to invade the world, that people would come together, and that fuckin’ idea was blown out of the water. Son of a bitch. We were actually invaded by aliens and we can’t work together. Grow the fuck up. As a kid, I watched this, and as an adult, I’m still watching this. And it irritates the hell out of me.
With the election obviously being a looming cloud that creeps closer every day in 2024, is that another part of the anticipation of being off the road, where you don’t have to get up there every night and rehash everything that’s happening and try to find light in it? Is there a part of you that’s looking forward to not doing that as much?
It’s like when Jon Stewart left The Daily Show, and everyone was questioning why he would do that. Well, it’s because all you’re doing at a certain point is repeating things and finding new ways to do the same joke, and I’m tired of finding new ways to do it. With as many ways as I can do it, it has no real effect. It has an effect that night where people laugh at what I’m saying, and then it doesn’t have an effect on anything else.
Every special I’ve put out, there are those type of jokes where it’s “Democrats do this, Republicans are that,” and I’ve come through all of this, and now it’s even worse.
What you and Jon do is an inspiration to me, really. I grew up politically active, but doing what you do would burn me out on things so quickly, but folks like you and Jon have helped so many people articulate their frustrations in easily accessible ways, for sure. I’ve always shared my appreciation for you and your work, but seeing you continue to push through and make it this long in doing that, I have to hand it to you once more.
Well, that’s very kind. I sincerely appreciate that, because you have no sense of that when you’re out there wondering around like you’re going psychotic in the desert. [laughs]
I’m very excited for you to be able to take this time off the road, and for us to be able to get Lewis Black in other ways. Even with everything that we’ve talked about you doing after the tour is over, what are you looking forward to most about these shows in Boston, and barreling towards the finish line by the end of the year?
What I’m looking forward to is that, over my years of being there, there has been a mutual love affair, if I might be so bold, between me and the audiences in Boston, so I’m looking forward to being in front of a crowd like that. The last time I played The Wilbur, the level of energy in the room was extraordinary and lifted the level of my act, and that’s what I’m looking forward to. Also, I’ve got nothing to be afraid of anymore, and nothing to prove, so now I’m feeling like I’m having the same type of fun with it that I had when I first started. What I’ve realized in doing these final shows, and this goes for anyone in any profession, is that I didn’t take the time to absorb what was going on. I didn’t pay enough attention to what was happening in life. It’s that thing you learn about later on in life and you try to tell someone younger about it, and they go “oh, yeah!” and then they don’t do it either.
With that in the mind, in terms of stopping to smell the roses, if you will, is there any advice you can give to comedians who are looking to build their presence out on the road from the perspective of someone who has done it so well for so long?
I believe that there’s something to be learned, as it has created a whole other audience, by performing on TikTok and YouTube, but really in the end, you learn the most about performing when you’re in front of a live audience. Another reason why I’m kind of leaving is because we’ve moved into a different age of performing. I’m the end of the industrial comedy age, so for the people that are breaking through in the technological age of comedy, go perform in front of people. There’s no small audience, whether there’s 10 or 50 people in the room, you need to perform as much as you possibly can in front of other human beings. Or you can get an AI-generated crowd that loves you.
I’m not disparaging it, but it’s just the way you learn your chops, and learn and grow. I don’t know how else to do it, because that’s the way I did it. One thing I do regret or wish we had back in the day, though, is camera phones, because when I was running the West Bank Cafe, we had tons of shows that we never recorded. But performing for someone watching on their phone is great, but I really do think you need to have someone sitting in front of you.
Class is in session, I couldn’t agree more. You’ve always been so good to us, Lewis, and it’s always been a pleasure checking in with you over the years, and I look forward to seeing you conquer the stage in Boston one more time.
Thank you very much, Jason. That means a lot, and it’s always been a pleasure to talk to you, as well. Take care of yourself.
LEWIS BLACK :: Saturday, September 28 to Sunday, September 29 at The Wilbur Theatre, 246 Tremont St. in Boston, MA :: 6 p.m. both nights, $49 to $89 :: Advance tickets