Bob Mankoff, Cartoon Editor for Esquire
Photo Courtesy of Bob Mankoff


Bob Mankoff, Cartoon Editor for Esquire

In my conversation with Bob Mankoff, the esteemed Cartoon Editor for Esquire, I had the opportunity to examine the mind of one of the most renowned cartoonists of our time. Bob shared his fascinating journey from The New Yorker to Esquire, shedding light on how the dynamics of his role have evolved to become more collaborative in nature. Unlike the more individualistic submission and selection process at The New Yorker, his current position allows for a richer interaction with fellow creatives.


Listen to Bob Mankoff tell his Story


Bob opened up about the critical role that collaboration plays in the realm of humor and cartooning. He recounted his journey, revealing that his knack for humor was evident as early as his school days. Despite this early realization, he opted for cartooning over stand-up comedy, significantly shaping his career.

We also discussed the nuances of his creative process, mainly how he masterfully balances visual elements with captions to bring his cartoons to life. However, creating humor in today’s culturally sensitive landscape poses its own set of challenges. Bob emphasized the importance of being provocatively thoughtful to engage audiences without crossing lines.

Bob’s involvement with artificial intelligence to enhance human creativity was an intriguing aspect of our conversation. He is pioneering efforts to merge technology with human ingenuity, aiming to explore new frontiers in the creative process.

Bob’s journey is a testament to the power of curiosity, resilience, and risk-taking. He underscored the importance of generosity and a collaborative spirit, which he believes are indispensable in the creative industry.

Through our discussion, Bob Mankoff provided a glimpse into his illustrious career and imparted valuable life lessons and insights into the ever-evolving world of humor and creativity.

This short reflection on my conversation with Bob Mankoff offers a glimpse of his story. However, for the full spectrum experience, try scrolling back up and listening to the entire conversation to unlock the complete story.

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