New Yorker cartoonist David Sipress talks about drawing, the purpose of cartoons,
and the family mishegas that continues to inspire him
“There’s almost nothing I’ve experienced in my life that I haven’t made a cartoon about,” says renowned cartoonist David Sipress. His career has spanned more than 50 years, the most recent half at the New Yorker, for which he has produced more than 700 single-panel cartoons.
His new memoir, “What’s So Funny?”, is a multifaceted and engaging look back at his development as a cartoonist and his upbringing in a family that didn’t exactly embrace it. His book features exactly the kind of mid-century New York Jewish family characters who inspired Mel Brooks and Larry David among others, and some of their arguments will be wryly familiar to many readers, especially those of Sipress’ generation.
His father Nat is the self-made owner of Revere Jewelers, whose clients include Oscar Hammerstein, Cyd Charisse and Zero Mostel. He always gets his price even while being robbed, defines success as respectability and thinks cartooning sounds like too much fun to be real work. Sipress’ mother Estelle, prone to migraines and excessive worrying, always puts her husband first, though her playfulness sometimes pokes through in unexpected ways. His older sister Linda torments him with pranks and the only secrets she keeps are her own. And David dreams from a very young age of becoming a cartoonist—not just any cartoonist, but a New Yorker cartoonist.
But there are no easy comedy clichés. Sipress’s cartoons and vignettes are integral to his slice-of-life storytelling, even in grim scenes. They capture his instinctive response to the family mishegas at any given moment and make it feel universal as only cartoons can.
And yet, he says, he almost didn’t include them until he asked his wife to look over the finished first draft. “She jokes that she had to have two therapy sessions before she had the conversation with me. What she had to tell me was, ‘David, it’s not good. It’s not funny, and that’s not who you are. You are funny.’ And she was right, that is who I am.”
What helped him then was trusting what he calls his cartoon brain. “There’s a part of my mind that’s always asking, ‘what’s funny about this, is there something here I can use, something I can make a cartoon out of?’” he says. “Cartoons have always been a way for me to navigate the difficult stuff I’ve faced. Humor and creativity have always been the things that saved me. When I was trying to write my reactions to things that I experienced, I found that I was always coming up with cartoons—even about the awful things—so I had to revisit the book with that in mind.”
Sipress grew up on Manhattan’s Upper West Side in the 1950s and ’60s, and the city figures prominently in many of his cartoons, most famously the one where a father walking in Central Park tells his son, “The sun rises on the Upper East Side and sets on the Upper West Side.”
Every line in his cartoons appears to move, and even the buildings in his Manhattan skyline for the book cover seem incapable of sitting still. His style looks simple, but as his New Yorker colleague Bob Weber once tested out, it’s very hard to imitate.
“I’m not trained as an artist; I’m self-taught,” says Sipress. “From the very beginning, I wanted my style, my drawing to look like, ‘David thought up the cartoon and he drew it.’ There’s a certain joy in that kind of drawing for me….In the very beginning of the book I draw a picture of the instrument I draw with, a crow-quill pen. I say in the book that I like it because I can’t control it. It’s a stiff implement that you dip into ink and draw with. There are going to be inexact things, there’s going to be mistakes, and I like that, it adds to that sense of movement and spontaneity.”
His preference for single-panel cartoons came early, thanks to his parents’ copies of the New Yorker. “I was completely entranced by the drawing, by the humor, by the stories in them. Even though I didn’t understand half of them, immediately they made me want to start drawing.”
He drew his first cartoon at age six, and soon began pasting his own cartoons over the ones in the magazine, to his mother’s amusement. “As a kid, I simply was obsessed with those cartoons. One thing that made me excited about them: We lived across the park from the Metropolitan Museum of Art. My mother used to take me and I’d look at the paintings and the sculptures and I thought, those are great but they look so hard to do, and cartoons looked easy and something a kid could do.”
The New Yorker cartoons had another advantage, because his father forbade comic books in the house. “We’re talking about the 1950s and early ’60s,” he explains. “My father was not atypical, coming from his immigrant past and wanting his children to have only the most challenging educational activities on their agenda. Comic books were famously considered as the opposite of that, dangerous in some ways. The cartoons in the New Yorker were different, they were somehow more sophisticated, less likely—I never understood it—to turn children into juvenile delinquents. As I say in the book, the only place I got to see comic books was at the barbershop.”
As he grew up, Sipress struggled with his parents’ expectations, particularly in math class, a theme that crops up frequently in his cartoons, but he loved history and pursued a graduate degree in Russian history at Harvard, where he was caught up in the student riots of 1969. He was also starting to draw and publish cartoons while he was there and after a year he dropped out to make a go of it professionally.
Telling his parents did not go well, to say the least, but cartooning eventually did. Within a few months he had a regular gig cartooning for a Boston alternative weekly, and he spent the next 25 years publishing in magazines and newspapers across the nation, from Learning for Teachers magazine to The Washington Post.
All that time, he was submitting cartoon roughs to the New Yorker every week and getting rejected, as were many other established cartoonists. Finally, at the age of 50, his first cartoon was accepted by the new cartoon editor, Bob Mankoff.
Mankoff eventually hired Sipress as a staff cartoonist and in 2010, selected him as the first daily cartoonist for newyorker.com. “Bob liked me for that because I’ve done a lot of topical, politically themed stuff. Every morning I would get up and sit down at breakfast with the New York Times and I had until 8 a.m. to come up with my idea. At first I was pretty stressed out, but almost immediately I realized I was starting to have what felt like a real, daily conversation with the readers. I drew the Daily Cartoon on and off several times, including during both presidential elections, and it was kind of thrilling…I’ve always tried, especially in my political work, not to hit people over the head with what I think, but focus instead on what we’re all feeling about what’s going on.. It’s always been amazing to me that I have responses to what’s going on politically, or in my life for that matter, and readers recognize themselves in my experience. That connection, miraculously, is where the humor happens.”
He regularly lectures on cartooning and participates in podcasts and roundtables with fellow cartoonists like Roz Chast, but says this is the first year he’s presenting to Jewish audiences specifically. However, this February, when his memoir came out, he was interviewed by NPR’s Terry Gross, whom he’d featured in a New Yorker cartoon a few years ago. Perhaps inevitably, they traded notes on their parents’ yiddishisms.
David Sipress will present “What’s So Funny? A Cartoonist’s Memoir” on Saturday evening, December 10 at Pasadena Jewish Temple and Center as the final event of the Jewish Federation’s 24th Annual Jewish Book Festival. For more information and to register for the event, visit www.jewishsgpv.org/jewish-book-festival or contact the Jewish Federation at 626-445-0810.
Deborah Noble is a member of the jewish Federation’s Jewish Book Festival committee and a contributing writer for JLifeSGPV.