Ruben Bolling — the nom de plume of “Tom the Dancing Bug” cartoonist Ken Fisher — seems to be doing pretty well for himself. The Tufts and Harvard Law grad’s strip is nationally syndicated via Andrews McMeel; Clover Press is in the midst of publishing a beautiful set of full-color paperbacks collecting his complete works; and he was just given a coveted Reuben Award by the National Cartoonists Society. Oh, and he was a 2021 finalist for the Pulitzer Prize in Editorial Cartooning.

But one gets the sense he might give it all up to live in a world without Donald Trump. 

“I don’t take Trump lightly. I don’t think he’s necessarily funny or a clown,” Bolling says of the former president. “I think he’s unbelievably dangerous, and the movement behind him is an existential threat. So my job is to make fun of that — sort of whistling in the dark. 

“[I’m not] saying that they’re not a threat, so we can make fun of him,” he explains. “It’s more, they’re a huge threat. So let’s laugh a little bit for a second before we, you know, continue fighting, or whatever we need to do to deal with it.”

For his part, Bolling is fighting via sharp political satire that became increasingly Donald-centric in the years since Trump first ran for president in 2016. It was a big change for a cartoonist who, when he started drawing during his days back in Boston, was almost totally apolitical. But he says he made a conscious decision to shift when he saw Trump’s ascendancy and what it could mean.

“I still do general humor ones every now and then,” says Bolling, citing his goofy ongoing “Super-Fun-Pak Comix” that satire comic strip tropes. But the state of the nation “is what I’m thinking about, it’s what I think people want to read about.”

Meanwhile, the New York resident retains his ties to the city he describes as being key to his “origin story.” “In addition to having a daughter who goes to Tufts, I have a daughter who lives there … and so I go up there all the time,” he says. “I feel like Boston’s my second home.”

Also, as a Mets fan, he feels he and the Hub share a common enemy: “We just want the Yankees to lose.”

On a recent episode of the Strip Search comic strip podcast, Bolling talked about his Boston-area history, and his pivot from doing silly pop-culture humor to skewering the Trumpverse (as it’s referred to in his latest Clover Press collection, “Into The Trumpverse”).

Some responses have been edited for length or clarity.

Boston.com: You spent a good chunk of time in the Greater Boston area. What cartooning were you doing, and what were you thinking about your future? And how did Boston play into that?

Ruben Bolling: Well, yeah, I mean, Boston is definitely part of my origin story — it is my origin story. My time there was incredibly formative. 

I always liked cartooning. I didn’t know if I was good at it. In fact, I was not good at the time, because I wasn’t really even trying. I did it a lot as a little kid, and I always thought maybe I could do it, but I didn’t do it. So it was at Tufts that I applied to the Tufts Daily to be a cartoonist there, and I was rejected — and deservedly. It was very bad. My comics were not good. They didn’t even show potential. They were just bad. I was trying too much to be like “Doonesbury,” who was my hero at the time, and “Bloom County,” that kind of cartooning, and I don’t know if I ever could have done that. But I certainly couldn’t do that at that time, because I had done almost nothing as an adult or young adult. So I really failed. And then, you know, I’m looking at career options and cartooning was not even a glimmer of a thought at that time. 

So I go to law school and there’s an ad in the law school newspaper, saying, we need a cartoonist, can anybody help us out? So I thought, OK, it’s the lowest stakes possible because it’s a law school newspaper, they’re begging for a cartoonist there, I’ll try. And at that time in Boston I was just starting to get back into reading comics. I always liked “Doonesbury,” but in high school and college I sort of rejected consciously my interest in, like, superhero comics, and being a comics nerd — I did not want that to be my persona. [laughs] I was rejecting myself, and it wasn’t until I went to law school that I began to say, you know what, that’s who I am, maybe I should pursue that interest, I’ve always loved it. There was a comic book shop in Cambridge, Million Year Picnic?

We know it well. It’s still there!

I would go there and, you know, satisfy my itch for the superhero comics for the first time in years, but also get into some of the underground alternative comics there. One of them I picked up was a Zippy book called “Are We Having Fun Yet?” by Bill Griffith, and it sort of rearranged my thoughts of what I could do as a cartoonist. I didn’t have to be a “Doonesbury”-style cartoonist, that kind of, you know, wry sense of humor. I could have a silly sense of humor and non-sequiturs and satire. 

And so I applied to the law school newspaper with a comic that was very different, that was really just exactly what I do — I just sat down and just did what I do now. And it was instantly satisfying to do. I knew it was good, in the sense of, “It doesn’t suck” [laughs], and it became very popular.

And that’s when I sort of realized, in the middle of law school, you know, maybe I could be a cartoonist. So for a long time I did both. But yes, it was law school and my time in Boston that really opened my eyes to what I could be as a cartoonist. And then as a young lawyer, I started “Tom the Dancing Bug” as a weekly comic strip that I did pretty much on the side.

How has “Tom the Dancing Bug” evolved over the years? The Trump Era has no doubt played a big role — Donald Trump, I don’t know if you remember him, he was president for a while? 

I’m drawing one about him this week! Every time I think he’s going to go away … He’s in the news again, believe it or not, if you look closely. [laughs] 

When it started, it was very general humor — it was apolitical. There was no politics in it. It was all silly humor about pop culture, or about nothing, or about cartoon characters, it was just very silly. That’s when I started professionally 32 years ago, so that’s a long time ago. The whole idea of the comic would be whatever I want to do that week. 

I started, you know, getting a little bit into politics, because I began getting interested in it as I got older, and also I got into it from the perspective of a humorist, because I’m just trying to think of funny things every week, and that’s an opportunity for something else I could write about. So I just began doing little bits of it more and more, just to try to be funny, anything to be entertaining — whatever I thought would hit. 

9/11, things changed, it got a little more political, the [2008] financial crisis a little bit more, and then, when Trump started to gain in the polls for the primary in 2016, I made an actual conscious decision. I said, I’m going to give my comic strip over to this, because this is the political phenomenon of my lifetime. This is an incredible thing that’s happening here. And I expected, and certainly hoped, that it would only last until the election. But then he got elected, and then I was stuck with him for four years. 

And then, when he leaves, he doesn’t go away. He doesn’t fade into the background like Carter, he’s just there! He’s definitely still in our face, and even when he was less in the news, I was still doing a lot about the Trump phenomenon, the MAGA people, and there’s no doubt now that this is the political phenomenon of our lifetime. So the strip has gotten very political. Even if I try some weeks to not do something about it, when I sit down and face that blank page, the synapses just … There’s like a groove that just sends me right down to Trump.

And I bet if you try to do something apolitical now, your readers will try to read something political into it.

Yeah, you’re totally right. And I’m very aware of that. When I do something that’s not political, by the fifth panel they’re like, where’s the political allegory? So I have to do [non-political strips] more in order to fight against that. I can see in the comments sometimes, when I look at them online, that people will still make political allegories to things that have nothing to do with politics. So if I don’t want to be a fully political cartoonist I have to establish myself as that — because the last five years I definitely set up a pattern. So yeah, I would love to get back to, you know, silly stuff. But this week there’s no doubt — I just knew it’s got to be what’s going on with Trump.

With so many lawsuits and investigations going on right now, do you think we’re finally going to see some accountability there? 

I’ve always been skeptical — in the past when people said, let’s see him wriggle out of this one, I was always like, oh, he is so going to wriggle out of this one … once he got past the “grab ’em by the p****,” that was it. You realized, nothing is going to stop him, he has a cult, and they will forgive anything, and he has his fingers on all the levers.

Obviously I have no insight as a pundit, or certainly not as an insider. But yeah, the same as you, I feel as though there’s just a lot of stuff now. There’s many things going on. Something’s got to at least penetrate a little bit.

Having really dove into Trump and the state of the country over these last five or six years, this is something that’s in your head space every week. Does it get to you after a while? 

There’s stuff that I write about that can be very depressing. I don’t always have to deal with a tragedy. But sometimes I choose to, because I can find it … It’s painful, but it can be cathartic, and it can help me. I don’t know if it helps other people, I hope so. 

I just did a comic about the shooting in Texas, and I did it in a Richard Scarry style. Drawing, you know, the inside of a classroom in this sweet children’s book illustrator’s style. And before that I wouldn’t even allow myself to create a mental image of what it must have been like in those classrooms. I would think about it, and then banish it from my thoughts … So I forced myself to confront —it was horrible to have to draw that. But at the end it felt very cathartic.

After 9/11 I did a number of comics — I had all these thoughts that were so dark and puzzling, and I was able to bring it into my world and have some control over it and manipulate it, and it was very helpful because I felt like I was going from powerless to powerful, because now, this big thing is in my world, and I can manipulate it on on my terms. So for me — and I hope that translates to the reader — it can be very helpful.

The Richard Scarry cartoon — funny, is not the word for it …

It’s biting, and it’s scary.

Yeah, that was maybe the hardest thing I’ve ever done in my cartooning career. It was. It was painful and hard. And yet there’s parts of it that are just technical like, what does that ear look like? How does he draw a rabbit’s ear? So it’s weird to have this terrible thing, and be so emotional, and still be technical about the way you’re going to, you know, color a bookcase the way Richard Scarry would have. 

So yeah, it was a weird process. But it helps me, and the hope is that it translates to the reader.

Listen below for the full interview, including a discussion of Bolling’s cartooning methods, his approach to satire, the origin of the pen name “Ruben Bolling,” and whether Red Sox and Mets fans ever truly made up after 1986.

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