Bob Mankoff, Cartoonist and New Yorker editor

Aug 15, 2024

56:44

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For over 40 years, Bob Mankoff has been a driving force of comedy and satire at some of the most honored publications in America, including The New Yorker and Esquire. He has devoted his life to discovering just what makes us laugh and seeks every outlet to do so, from developing The New Yorker’s web presence to integrating it with algorithms and A.I.

For 20 years, Mankoff was the cartoon editor at The New Yorker magazine, which is famous for its single-frame black-and-white cartoons. In 2005, he created the “Cartoon Caption Contest” and it’s still in every issue of the magazine. Each week, the magazine publishes a cartoon illustration, but with no caption. Then, magazine readers come up with caption ideas and send them to the magazine. The contest is so successful that they get 5,000 caption submissions a week. Mankoff has partnered with Microsoft and Google Deep Mind to develop machine learning algorithms to help identify the funniest captions.

In 2018, Mankoff became president of cartoonstock.com, the largest cartoon licensing source on the planet. In addition to being a successful creator, Mankoff has studied the psychology of what makes us laugh. He’s developed insights into the creative process, for example in his 2002 book The Naked Cartoonist: A New Way to Enhance Your Creativity and his New York Times bestselling memoir, How About Never – Is Never Good For You?: My Life In Cartoons. His story was the focus of the 2015 HBO documentary Very Semi-Serious.

Mankoff is currently the cartoon editor at the weekly online newsletter Air Mail.

Chapters

0:00 Elaine from Seinfeld

3:58 The New Yorker magazine cartoons

8:45 Artificial Intelligence

12:20 The movie "Semi Serious"

19:00 A.I. and humor

27:40 The Cartoon Caption Contest

31:40 The Seinfeld episode "The Cartoon"

38:50 Having a sense of humor

44:10 A.I. and the Cartoon Caption Contest

51:10 The Reverse Cartoon Caption Contest