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The New Yorker Cartoonist David Sipress (ep. 452)

John O’Leary welcomes award-winning New York cartoonist David Sipress to the Live Inspired Podcast to share the inspiration behind his creations.

David Sipress is an iconic cartoonist for The New Yorker. Since 1998, he’s published nearly 700 cartoons largely based on perceptions of shared human experience, rooted in his life-long love of history.

With humor, creativity and vulnerability, David shares stories about his complicated family, the day he decided to pursue cartooning professionally and the 25 years of rejection that followed.

Don’t miss today’s intimate and engaging conversation with an artist who understands that personal thoughts and feelings often lead to remarkable ideas.

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  • Although his father immigrated from Ukraine in 1914, David didn’t know much about his past because of his unwillingness to share.
  • What about me? Initially noticing the heroics of his father’s actions, David grew resentful of how his father reacted to his jewelry store being robbed.
  • Stand-up comedy taught David the importance of timing and more notably, to find humor in the things that are most important to him.
  • While studying for his Harvard Ph.D. in Russian History, David left to pursue cartooning professionally, disappointing his dad profoundly.
  • Cartoon brain: David finds inspiration for his cartoons by listening, being aware all the time as well as examining his life for things that are important to him.
  • David’s first New Yorker cartoon was purchased before his father’s death, yet he wasn’t able to see it published.
  • Get a copy of David Sipress’ book What’s So Funny here.


Did you enjoy hearing from a cartoonist? You’ll love New York Times bestselling children’s author + illustrator Jarrett J. Krosoczka. In our conversation, Jarrett shares the lessons he learned after being raised by his grandparents, how he shared his unconventional childhood in his book Hey Kiddo and serves as another important reminder that what you’ve weathered does not have to hinder your opportunity to live a better, bigger, bolder life. Listen to Jarrett J. Krosoczka on ep. 318 now.



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  1. Q. What is the best book you’ve ever read?
    A. The Pigeon Tunnel: Stories from My Life by John le Carré.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. I didn't worry.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. The book of few photographs I have of my family, my proof of vaccination and my laptop.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. My mother and I'd like to know how much of who she originally was got snowed under by the need to take care of my father. I always sensed her and I had a deep connection.
  5. Q. What is the best advice you’ve ever received?
    A. My wife reminds me that we're all going to die some day, bad things are going to happen so why waste time worrying about things. Try to enjoy yourself a little more.
  6. Q. What advice would you give your 20-year-old self?
    A. Hang in there, kid. It will get better.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. David was an artist who spent his life trying to be a creative person and at the same time a good, kind and generous person. Failing often but always with his eye on his goal.