Cartoonist David Sipress talks humor and achieving the holy grail of publishing in The New Yorker

David Sipress submitted his cartoon ideas to The New Yorker for 25 years before the magazine gave him a tumble. He finally made his first New Yorker sale in 1997, with a drawing of a zen meditation class where someone blurts out “Are we there yet?”

“I’ve always considered that caption to be exquisitely appropriate,” Sipress writes in “What’s So Funny? — A Cartoonist’s Memoir” (2022, Mariner Press). The book chronicles his New York childhood, including this analysis of a photo of his father, who owned a jewelry shop: “A proud, self-satisfied first generation immigrant who only looks out, never in.”

There are family tragedies, love stories, dashed hopes, dreams realized and hundreds of funny drawings drawn.

The book is text-driven but profusely illustrated with cartoons spanning Sipress’ entire career, from childhood drawings, to the panels he drew for decades for the Boston Phoenix alt-weekly newspaper, to very recent New Yorker work.

The cartoons offer commentary on Sipress’ life story. Coping with parental expectations is a recurring theme. Parents tell their college-age child, “We’ve been thinking about what we want to do with your life.” Sipress’ Jewish heritage comes into play, as well as relationships.

Other Sipress cartoons are in the book just because they’re funny, like one of his first professional efforts in the 1970s, showing a man with one of those once-ubiquitous picket signs reading “No nukes!” standing next to a man with a demented smile and a sign that reads “No crannies.”

As he prepares to discuss his memoir in a virtual event hosted by the Mark Twain House and Museum on Thursday, David Sipress spoke with the Courant about his book, his decades of waiting for The New Yorker to notice him and the realities of being a professional cartoonist.

This is not the book many of expected from a New Yorker cartoonist. You took a very different path than the others who’ve written about their lives.

I think so. I had all these stories rattling around my head about my family, and that’s what I really started focusing on. I started doing essays for The New Yorker website around 2013, and the book grew out of that. When I showed it to my wife — who said she had to have two therapy sessions before she could have the conversation with me — she said “It’s not good,” and I said “What’s wrong?” and she said “It’s not funny. And you’re funny. That’s who you are.” So that’s when I started incorporating the cartoons into the narrative, and it made all the difference.

You’re old enough to remember the work of Peter Arno or Charles Addams, right?

I loved all those guys, especially because like Arno, or [Charles] Saxon, were drawing this New York I had fantasized about but which my immigrant Jewish family was not part of, this world which looked like everyone was elegant and drank martinis and, as I say in the book, didn’t worry about every little thing. I saw that world in their cartoons and that also fueled my longing to be part of The New Yorker.

So you diligently sent The New Yorker cartoons for 25 years before you got in?

For someone who does what I do, there’s really The New Yorker and then there’s everything else. It’s not just the holy grail, it’s more. I knew if I wasn’t in The New Yorker, I could never feel good about myself. People would ask me, “Why don’t you give up? Why don’t you stop?,” and I just couldn’t imagine that. Also, I’d look at the magazine and think “I’m just as good at that. It’s their problem, not my problem.”

Then, when the [cartoon] editor changed in 1997 and a friend of mine took over, Bob Mankoff, he immediately started buying my work.

There was the same editor there for that whole previous 25 years?

Just one, Lee Lorenz, who was also a cartoonist. Several years ago, I was on a panel with him at a museum, and he claimed he didn’t remember me and he never saw any of my cartoons. I wanted to hate him but I really couldn’t.

Who were The New Yorker cartoonists you were most fond of when you were struggling to get in?

I started wanting to be a New Yorker cartoonist when I was 6 or 7. As I say in the book, I would draw my own cartoons and tape them over the cartoons in the magazine. Back then, the cartoonist that really fascinated me was Saul Steinberg because of what he would do with a line. A lot of the conceptual stuff you were talking about comes from my worship of his work. He would make stuff work with simple lines that I really wanted to do myself.

Later on, there were other people. These days, as far as funny goes, there’s no one like Sam Gross, who is a real hero of mine as far as the funny part goes.

In that 25 years, were you sustaining yourself as a cartoonist, just not at The New Yorker?

Barely making an income, yeah, but enough to get by. The New Yorker is a whole other category in terms of what you get paid. Once I was in the magazine I was really able to support myself just being a cartoonist.

It’s still not particularly stable, because every week you hand in your 10 rough ideas and every week you sit and wait for the email to come to tell you whether or not you’ve sold one. It’s very competitive, and there are very few slots. These days there are a lot of people vying for those slots, so you never feel 100% secure. There’s always that anxiety. Mort Gerber, the cartoonist, once said cartooning is one field where you can be unemployed and not know it. Meaning that you never know when they’re going to buy another one.

I’m called a staff cartoonist, and that refers to a bunch of things. I have a contract and stuff like that. So I’m a little bit special. I’ve published over 700 cartoons in the magazine.

David Sipress discusses his memoir “What’s So Funny” with fellow New Yorker cartoonist Pat Byrnes in a virtual event hosted by the Mark Twain House and Museum, Thursday at 7 p.m. The event is free, registration is required. marktwainhouse.org.

Christopher Arnott can be reached at carnott@courant.com.