The New York cartoonist reflects on his long career in Boston

Before David Sipress fulfilled his childhood dream and published over 700 cartoons for The New Yorker, he was a regular in the Boston Phoenix. This trip is featured in her new memoir, “What’s So Funny?” and he joined morning edition welcomes Paris Alston and Jeremy Siegel to talk about his career.

His love of comics began young when he cut out his own cartoons and pasted them over existing cartoons in issues of his parents’ magazines.

“My parents had The New Yorker when I was a kid and I was fascinated by cartoons, and what I loved about them was that they looked easy to do,” he said. -he declares.

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Years later, as a graduate student in Soviet Studies at Harvard, he realized he would have to give up to pursue his dream.

“I wanted to be a cartoonist, but I never really crossed that threshold until I revealed it to my dad,” he said. “And it was a very difficult moment, which almost destroyed me, but I got through it and the rest is history.”

After dropping out, he sold his plays in Harvard Square for 10 cents each.

“The wonderful thing I achieved when I decided I was going to be a cartoonist was unlike anything I had ever done – I had a notepad, I had a pen and some ideas as a designer, and so I became one very quickly just having these articles,” he said.

He met someone who worked for Broadside, Boston’s first alternative newspaper, and then he went to Boston After Dark, which later became the Boston Phoenix.

“To my amazement, I walked in, they looked at my things, they said, ‘You are there.’ And so for the next 30 years, I was at the Boston Phenix every week,” he said.

Sipress Red Sox cartoon from The New Yorker.

David Sipress / Mariner Books

His time in Boston left an impact, even if it didn’t make him a Red Sox fan. Early in his New Yorker career, he created a cartoon of a man wearing a Red Sox t-shirt in a psychiatrist’s office, as he tells the patient, “Rooting for them is a disease. , Ben. There’s nothing to be ashamed of.”

“That was before the Red Sox became the fabulous team they are now,” Sipress said.

However, one day his phone rang and it was Red Sox CEO Larry Lucchino’s personal secretary who invited him to sit in his box at a game in Boston. He replied after a long silence, “It’s so ironic because I’m actually a big Yankees fan.”

“Another long silence and ‘we’ll have to call you back,'” he heard. “That’s the last I heard.”

At the end of the interview, Siegel noted that Sipress’s father had emigrated to the United States from Ukraine as a child, and asked how he felt about Russia’s invasion of the country as a than a designer and someone with roots there.

“I will say that I am not making jokes about it at the moment because it will take time for me to process this and for the world to be ready to make humor about it. It will be a long time from now,” said said Sipress.

“But when I do cartoons about this stuff, I never attack it head-on,” he continued. “I try to make jokes about how we feel about what’s going on, about our reactions, not about the thing itself. And if I ever get around to doing anything about it, that’s probably the route I’ll take.

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