BJV Interview: David Sipress on "What’s So Funny? A Cartoonist’s Memoir"

The New Yorker cartoonist talks to the BJV about his work and upcoming Jewish Literary Voices program

On Thursday, November 17 at 6:45 p.m. “Jewish Literary Voices: A Federation Series in collaboration with The Jewish Book Council” hosts The New Yorker cartoonist David Sipress, whose book What’s So Funny? A Cartoonist’s Memoir recounts his hapless place in his Upper West Side Jewish family in the age of Sputnik and JFK.

This free program will be presented via Zoom. Please visit our calendar of events at to register.

Throughout the book, cartoons appear in the narrative with spot-on precision, adding humor and insight to evocative profiles of his family and musings on creativity and art. Sipress’s poignant, compelling story is also a meditation on creativity and the art of cartooning, and the delightful Aha moments in answer to the perennial question aimed at cartoonists: Where do you get your ideas?

Sipress was born and raised in New York City. He graduated from Williams College in 1968 and went on to study Russian History in the Department of Soviet Studies at Harvard University. He left Harvard before completing his degree to pursue a career as a cartoonist.

David has been a staff cartoonist at The New Yorker since 1998. He’s published nearly seven hundred cartoons in the magazine. His cartoons have also appeared in countless other publications and he was the weekly cartoonist of The Boston Phoenix newspaper for 25 years. He was the 2016 winner of the National Cartoonists Society’s Reuben Award for Gag Cartooning.

David was the co-creator, writer, and host of “Conversations with Cartoonists,” a series of onstage interviews with New Yorker artists, including Roz Chast, Gahan Wilson, George Booth, and many others, at Dixon Place Theater in New York City. He has lectured widely on his work and the art of cartooning,

He lives in Brooklyn with his wife, Ginny Shubert, an attorney and activist who works on issues of health and housing.

BJV Interview: David Sipress

By Albert Stern / BJV Editor

Single-panel gag cartooning involves a mastery of imaginative compression – how to evoke a panoply of ideas and associations that can be apprehended by a reader through a single drawing and one or two lines of dialogue. To be effective, the best gags, no matter how outrageous the setup, must deliver punchlines that are broadly relatable to a reader’s everyday experience. Sometimes cartoons work by juxtaposing unlikely reactions to impossible scenarios and sometimes by zeroing in on an ever-so-slightly tweaking the ever-present, only slightly concealed, inanities of everyday life. A great cartoonist is a master of minimalism.

David Sipress is a master. He is a latecomer to the heights of his profession – he didn’t sell his first cartoon to The New Yorker until he was 50 years old, in 1998, after experiencing decades of rejections. Since then, more than 700 of his cartoons have appeared in the magazine and its website. As a memoirist, he is a latecomer, as well – his family saga, What’s So Funny?, was published in 2022, when he was in his seventies. Sipress is a native New Yorker who grew up in a comfortable, secular upper middle-class home on the Upper West Side; he perfectly captures the culture and cultural anxieties of the Jewish milieu in which he was raised. He also portrays – sympathetically, but with a mature frustration that is wholly appropriate – his overbearing father (a prosperous, hardworking jeweler), smothering homemaker mother, rebellious sister, and himself, a gifted child with “his head in the clouds” who is consistently brought crashing down to earth by their mishegoss and his own.

It is a first-rate and deeply humane account of growing up in a Jewish family in the mid-20th century – plus a story of artistic striving, struggle, and ultimate success, with plenty of cartoons. With What’s So Funny?, Sipress joins the ranks of his New Yorker colleagues, Roz Chast (Can’t We Talk About Something More Pleasant?) and Bruce Eric Kaplan (I Was a Child), as one-panel gag cartoonists who redirected their imaginations to create amazing long-form autobiographical works that are as readable and moving as any memoir produced by writers who work only with words. Plus, all three books are hilarious – by all means, check them all out.

And don’t miss your chance to hear David Sipress speak at our Federation program this November – he’ll talk about his memoir and answer your questions about cartooning (and cartoonists). The BJV caught up with Sipress in September and talked about going to college in the Berkshires, inspiration vs. perspiration, comic timing, and his Jewish identity. Our interview was edited for length and clarity.

You have a Berkshire connection, having gone to Williams College. What was your experience out of the Berkshires as a young New Yorker leaving town to a different kind of place?

Well, I had never been any place quite as beautiful as the Berkshires. When I arrived at college, I instantly had a feeling of peace I'd never had before, just because that environment just created that feeling in me. It was an interesting time. Being in that idyllic environment, both the landscape and the school itself in 1968, one felt very far away from world events that were about to come crashing down on the male college graduate who was eligible for the draft.

How did it affect your artistic progress?

At that time, my cartooning and my desire to be an artist were on hold. I seemed headed straight for an academic career studying history, specifically Russian history. So I can't really say there was much in terms of my artistic development, but my intellectual development was enhanced a million times because it was a terrific school. Classes were small. There was a lot of really wonderful teaching that went on, and so that part of it was really great for me. I only really came to appreciate it when I went to graduate school, and I was in lecture halls with 200 students, and I had been used to classes with ten people in them. So I really loved the school, and I'm so grateful for the education I got there.

But you went back to being an urban person after being in the country, even though you say you found some kind of peace here that you had experienced before.

Yeah, I mean, I moved to Cambridge after graduation, and then I stayed in Boston for 15 years. Then I moved back to New York. And if we're talking about my artistic development and the inspiration for the ideas for my cartoons, being in the city has been really important for that. There's so much going on. There's so much that happens in the course of a day that has been fodder for my humor and my cartoon. So I can't imagine not living in a city at this point.

How did you go from working as a cartoonist, in a medium where you have to cram a whole lot of information into a drawing so that the reader will get the caption, to opening things up and working in a long-form like memoir?

Well, that's a complicated and interesting question. My first response is that when I first sat down and decided I was going to write a memoir, I was a little bit flustered because I'd been so addicted to the single-panel cartoon creative process. That process is very quick. You get instant gratification, and then you're kind of done. You go get a cup of coffee. So how was I going to write something in long form? I had had a little practice because I had written essays for The New Yorker website, but still, the proposition was quite daunting. But what I discovered as I wrote was that on a good day, the ideas started to come just like they do for cartoons, but they came one after another, one building on another, so that the writing became not really all that different from the creative process of doing cartoons. And eventually, I developed the same addiction for [prose] writing that I'd had for doing cartoons.

Another thing is that cartoons almost always have a caption. Captions are dialogue. And when I started writing the book, I realized the easy part for me was writing dialogue, which flowed every time I came to a section where it was necessary. I attribute that to the thousands and tens of thousands of cartoon captions I've written in my life. I learned that skill, how to get a lot into a spoken sentence. But I will say this is that when I sat down and decided I was going to write this book, I did a drawing that kind of encapsulated my anxiety about it. And it's a person sitting in front of their monitor about to write that says, “Nothing Interesting Has Ever Happened to Me. A Memoir.” I wasn't sure I had the material in my life, but again, as many writers say, you can't really write until you start writing. And once I started writing stuff, the memories came back and the stories came back and it got easier and easier.

In the chapter titled “Comedy,” you write about comic timing. I know that for a comic writer, or a comic anything, talking about the idea of comic timing is very challenging, but that's what I'm going to ask you to do –  share some of your ideas on what makes for good comic timing.

In my one step into stand-up comedy in high school, I learned very quickly that a lot of it's about patience, about waiting until exactly the right moment to finish the joke. I can't quite explain it. I'm a person who's pretty much a slave to my anxieties for most of my life. But when I get up in front of an audience, for whatever reason, I always feel completely at peace and relaxed. And I think to do comic timing, you have to be relaxed and patient. My wife says it's because finally, everybody's paying attention to me, which is what I really want. But as far as comic timing and cartoons, the point I make in the book is that there is a kind of comic timing that's intrinsic to the single-panel cartoon and it has to do with the fact that the reader almost always first looks at the picture, takes in the picture and then waits. There's a little beat that you wait trying to figure out what's going to come next, and then you read the caption. And that is the built-in comic timing in the single-panel cartoon.

Beyond that, for me as a cartoonist, that also works a lot of the time. If I ever begin with a drawing and I don't know what the caption's going to be? Sometimes the timing takes a minute, and sometimes it can take many months before I come up with the line that goes with that drawing. When ideas come that way, they take you by surprise and there's an intense pleasure that is difficult to describe. But it's about as happy as I could ever be in that moment when the light bulb goes on. And it really is what keeps me doing what I do, constantly hoping for those moments.

When I read about your process, it seemed to me that there is more inspiration than perspiration in your cartooning. Maybe the inspiration is the perspiration for you.

What you say about the inspiration being the perspiration is the way it is. It's a lot of work, mental work. I'm in my studio right now and squeezing my brain, trying to review my experiences or something that pops into my head and trying to turn it into a cartoon. It's hard work, but it's work that I've been doing since I was six years old. So I'm kind of used to it. And to me, it's perspiration, but also pleasure. I love doing it. And the drawing part, which is part of the process, once the idea comes, can be labor intensive. I, however, differ from a lot of cartoonists in that the way I draw, I draw in a really direct fashion, spontaneous fashion. I don't labor too much over the drawings because I think that takes away from their impact. So I like the quick, spontaneous drawing that I do, and that may be less perspiration than other cartoonists.

How many iterations of a drawing might you go through before you find the right one?

[New Yorker cartoonists] hand in rough drawings from which the selections are made by the cartoon editor and then ultimately by David Remnick, the editor. So things always begin with a rough drawing, and sometimes I can work for hours, redrawing and redrawing. Then I look at that rough drawing and I think, well, that's the best drawing I've done. And I'll hand that in. But sometimes it can come quickly and there's one iteration or the thing itself, and then other times it could take me hours to get the drawing just right. But I always try to keep a sense for the reader to feel, “Well, David thought it up and he drew it direct like that.” I try to keep a spontaneous effect.

What has your Jewish identity meant to you over the course of your life?

Well, growing up, it was always very complicated and confusing, as I say in the book. And the specific example, again, is that we celebrated both Hanukkah and Christmas, so I was never really sure exactly what kind of Jewish we were. My father had a complicated relationship with his own Jewishness, and I think that had a lot to do with his alienation from his original family that lasted a lifetime. I identified on some deep, fundamental level – I knew certain things about myself that I attributed to my being Jewish and one of the most important, I have to say, was my sense of humor. I knew that there was something Jewish about my sense of humor. And also I just felt like I grew up in New York City. So until I went off to Williams, I was pretty much surrounded mostly by Jewish people. But when I got to Williams, I began to understand that I was different from other people. And I did now and then run into a little of what I can only call antisemitism, but none of it has resulted in my becoming a particularly religious person. My identity for me is pretty much always been cultural rather than spiritual.