The New Yorker Cartoons

The New Yorker Cartoons


As young children, many of us were taught that humour is silly and a waste of time. And so, while five-year-olds laugh hundreds of times a day, adults are down to about fifteen. That’s not good.

Humour has its benefits. It’s physically and psychologically healthy, especially in the way it blocks stress. Secondly, humour makes us mentally flexible — able to manage change, take risks and think creatively. And thirdly, humour serves as a social lubricant, making us more effective in dealing with colleagues and clients.

One quintessential manifestation of humour is the single-panel cartoon, and at the top of that particular food chain lives the New Yorker cartoon.

The New Yorker has featured cartoons in its magazine since it began publication in 1925.

For this story we collaborated with Bob Mankoff, the ultimate New Yorker cartoon insider. Mankoff is the president of CartoonStock, the world’s largest database of single-panel cartoons, but prior to this he was a staff cartoonist for The New Yorker for thirty-five years and its celebrated Cartoon Editor from 1997 to 2017.

In that later role, Mankoff would review over a thousand cartoons a week in order to help select the 15 or so that got into the magazine. It’s not easy to get your cartoon published in The New Yorker, and indeed there is an entire subculture that has grown up around the rejected New Yorker cartoon. It even took Bob three years and 2,000 submissions to see his name in the corner of one of his cartoons. More than talent, getting published in The New Yorker takes dogged perseverance.

The most reprinted New Yorker cartoon of all time is Peter Steiner's 1993 drawing of two dogs at a computer, with one saying, "On the Internet, nobody knows you're a dog". You’ve probably seen it. Mankoff’s best known cartoon also serves as the title for his 2015 memoir: How about never – is never good for you?

The notion that some New Yorker cartoons have punchlines so oblique as to be impenetrable became a subplot in the Seinfeld episode "The Cartoon”. You can watch those scenes HERE.

So, what’s funny? In this 2014 TED Talk Mankoff offered up some key insights into what the magazine is looking for in its cartoons (incongruity, dispositional humour, cognitive mash ups), as well as what it’s not interested in (gross-out jokes, mild child-centered cannibalism). He also talks about the essential futility of analysing humour.

Since 2005, and also thanks to Mankoff, The New Yorker has published a cartoon without a caption every week and asked readers to compete to write the winning caption. In 2016, the magazine began relying on an algorithm to sort the 5,000 to 10,000 caption entries per cartoon by funniness, aggregating voters’ opinions to present ranked lists. The combination of the prestige of the New Yorker cartoons and the unique quality of this dataset (making thousands upon thousands of cartoons publicly available and easily scraped) presents the opportunity to give computers what they have always lacked: a sense of humour.

And indeed the hottest new topic in the cartooniverse is the potential role of artificial intelligence.

AI is getting closer to understanding what makes something funny. Perhaps unsurprisingly, considering the rapid advancement of large language models, it’s starting with those captions. The latest models have become surprisingly adept at understanding why something is funny. AI isn’t writing jokes yet, but it seems to be grasping the concept of what made a particular joke work, and the ability to understand humour is a key stepping stone toward the ability to create it.

Having said all this, Mankoff, in a Google-sponsored piece that he wrote for The Atlantic in 2023, says:

“I have no wish to welcome our cartoon overlords. But there’s also no need for me to shun AI models as potential collaborators, creative assistants or inspirers. Cartoonists have shown that they are alchemists extraordinaire. I’m convinced they will be able to use this tool to augment their alchemy. I’m just as sure there will never be a day when robot cartoonists are creating robot cartoons for robot readers of The New Yorker to laugh at.”

Story Idea: Bob Mankoff



1. Bob Mankoff with his best known New Yorker cartoon
2. The cover of the first issue of The New Yorker, drawn by Rea Irvin
3. Wall of covers in The New Yorker office
Video Trailer: Very Semi-Serious: A Partially Thorough Portrait of 'New Yorker' Cartoonists, 2015
5. The New Yorker rejection letter
6. Peter Steiner's 1993 drawing of two dogs at a computer, with one saying, "On the Internet, nobody knows you're a dog". Credit:
7. New Yorker cartoon by Roz Chast, 2016. Credit:
8. New Yorker cartoon by Robert J. Day, 1961. Credit:
Video Highlights: Elaine Tries To Understand A Cartoon  in "The Cartoon", Seinfeld, 29 January 1998.
10. Video: Anatomy of a New Yorker cartoon, Bob Mankoff, TED New York, 2014
11. Book: How About never--is Never Good for You?: My Life in Cartoons, Bob Mankoff, March 2014

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