The Psychology of Humor || Bob Mankoff

October 12, 2023

Today we welcome Bob Mankoff to the podcast. For over 40 years, Bob Mankoff has been the driving force of comedy and satire at some of the most honored publications in America, including The New Yorker and Esquire. He is the founder of Cartoon Collections, parent company to CartoonStock.com, the world’s most successful cartoon licensing platform. For twenty years as Cartoon Editor for The New Yorker,  Bob pored over thousands of submissions each week, analyzing, critiquing, and selecting each cartoon. In 2005, he helped start the “New Yorker Cartoon Caption Contest.” Bob is the author of numerous books, including his New York Times bestselling memoir, How About Never – Is Never Good For You?: My Life In Cartoons.

In this episode, I talk to Bob Mankoff about the psychology of humor. Looking back at his illustrious career as a cartoonist, Bob talks about his early beginnings and the people he’s mentored in the field. He explains the anatomy of a joke and reveals his all-time favorite cartoons. While humans are creative creatures, Bob believes that using AI and technology can further augment our intelligence and humor by opening up worlds of possibilities. 

Website: www.bobmankoff.com/

Twitter: @BobMankoff


  • Bob’s childhood & upbringing
  • Personality of cartoonists and comedians
  • Types of humor
  • The grand scheme of time
  • Augmenting intelligence and creativity
  • Cartoon Bank
  • All-time favorite cartoons
  • Theory of humor
  • Censorship & cancel culture
  • Bob Mankoff’s legacy

Sponsor Information

Unlikely Collaborators

Today’s episode is sponsored by Unlikely Collaborators. Their mission is to untangle the stories that hold us back—as individuals, communities, nations, and humanity at large. Using the Perception Box lens, they do this through storytelling, experiences, impact, investments and scientific research. Unlikely Collaborators: The Only Way Forward is Inward.

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