Meet Bob Mankoff—the droll, wildly successful cartoonist who edited cartoons for The New Yorker for two decades. After that stint, he went on to launch other cartoonists’ careers at Esquire and is now at the arts and culture website Air Mail doing what he has loved doing for almost half a century—editing cartoons.

Now here’s the cartoon that Bob Mankoff said put his daughter through college and enables his third and current wife to ride horses: A man is standing at his desk against a stark backdrop of skyscrapers. He’s on the telephone consulting a paper calendar (it was drawn in 1993, after all), and the caption is: “No, Thursday’s out. How about never—is never good for you?” In 2014, Mankoff published a memoir that he titled with the same trademark punch line, “How About Never—Is Never Good For You? My Life in Cartoons.”

Mankoff was in the house—or more accurately at Temple Israel of Boston—last week promoting his new book, “Have I Got a Cartoon for You! The Moment Magazine Book of Jewish Cartoons,” at a program sponsored by Jewish Arts Collaborative (JArts). Introducing Mankoff, JArts executive director Laura Mandel promised he would answer the question of how the “people of the book” became the “people of the joke.”

Mankoff’s very funny PowerPoint presentation went quickly to the heart of the matter. He asserted that the Torah is not that funny, but there is inherent humor in many of the commentaries that surround Talmudic passages. As for the classic Jewish joke, Mankoff said, “A conflict and a tension are at the heart of Jewish humor.” He illustrated his point with the following joke: A bridegroom goes to the home of a potential bride with a matchmaker. It’s a beautiful place, full of fancy furniture. The young man asks, “How do I know the furniture isn’t borrowed?” To which the matchmaker replies, “Who would lend to these people?”

At 75, Mankoff said he’s still enamored of the old Borscht Belt comics. As a child, he spent his summers in Catskill resorts like Brown’s Hotel, Grossinger’s Catskill Resort Hotel and Concord Resort Hotel. “I was influenced by Buddy Hackett, Alan King, Jerry Lewis, Jackie Mason and Rodney Dangerfield,” he said. “Who knew you could be funny for money? I loved the rhythm of their jokes with a punch line and then the reveal. That was what I was matriculated on growing up Jewish in Queens.”

In the early 1970s, Mankoff toyed with the idea of becoming a stand-up comic. In a conversation that followed his presentation, he told interviewer Ben Brock Johnson that he realized stand-up was not easy to do in 1973. “The Concord was not my audience,” he said. “They didn’t like alternative comedy. My humor was too absurdist for them. They were used to Rodney Dangerfield jokes.”

Mankoff eventually used his comedic riffs to great effect in his cartoons. When he began sending his work to The New Yorker in 1973, he mentioned to his father that he was trying to be a cartoonist. “This was after I quit graduate school, or graduate school quit me, and my father said they already have people who do that,” he said. “And I told him, ‘Yeah, but one of them might die.’” Although Mankoff could not confirm whether someone’s death was responsible for his career, four years and several rejections later he sold his first cartoon to The New Yorker in 1977.

At The New Yorker, Mankoff became known for cartoons that he described as “strictly visual with wordplay. There was the one with three buckets. One had an H, and two had the letter O. Another cartoon with the caption ‘Hamlet’s Duplex’ depicted two doors side by side, numbered 2B and Not 2B. There’s a contradictory logic inherent in those kinds of cartoons.”

During his 20-year editorship at The New Yorker, he created the cartoon caption contest. When the contest debuted in 1998, it was an annual event. Soon after, the feature was weekly. “We had to figure out how to stagger it so thousands of people could enter the contest,” he said. “No one can look at 5,000 to 10,000 captions a week. There’s a lot of repetition.” Mankoff eventually worked with an artificial intelligence researcher to create an algorithm that tallied the entries and detected similarities.

As for the eternal question—why are Jewish people funny?—Mankoff retorted: “That’s news to me. It’s not because of persecution. We have a yiddishe kop, and we turn logic on its head, and that makes for a certain kind of Jewish joke. Before the 19th century, Jews weren’t particularly funny. Then you had the Hasidim versus the assimilationists, and it was a hotbed. But they weren’t going to kill each other. They didn’t have armies like the [non-Jews], so they made jokes. By 1920 there were more than a million Jews in New York. They were coming over in droves and did vaudeville, then radio. It was the first time Jews were funny for money.”

With regard to his Jewish and spiritual identity, Mankoff said he’s not a strident atheist, but he remains a firm skeptic. “There are conflicting religious and competing claims on who has the best imaginary friend,” he said. “My mantra is ignorance is knowledge. When people get absolutely certain about something, that’s when I’m suspicious.”