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Bob Eckstein: Creating Laughter in the Toughest of Times

Humorist and cartoonist Bob Eckstein talks about his goal of making people laugh, even in the toughest of times, through two new books.

Name (byline): Bob Eckstein

Literary agent (if one): Joy Tutela, David Black, Inc.

Book title:

All’s Fair in Love & War: The Ultimate Cartoon Book by the World’s Greatest Cartoonists (Princeton Architectural Press, October 2020)

The Elements of Stress (Humorist Books, October 2020)

Genre/category: Humor

Elevator pitch for the book:


All’s Fair in Love & War: The best cartoons in the world on the topic of love, marriage, and divorce. | IndieBound | Amazon

[WD uses affiliate links.]


The Elements of Stress: Invaluable handbook to handling stress in our time—things could not get worse but they could get funnier. Written with Michael Shaw. | IndieBound | Amazon

Previous titles by the author:

The History of the Snowman (2007, Simon & Schuster)

Footnotes From the World’s Greatest Bookstores (2016, Clarkson Potter Style)

The Illustrated History of the Snowman (2017, Globe Pequot)

The Ultimate Cartoon Book of Book Cartoons (2018, Princeton Architectural Press)

Everyone’s a Critic: The Ultimate Cartoon Book (2019, Princeton Architectural Press)

What prompted you to write this book?

The pandemic. Trying to find ways to get through this (me, my friends, everyone) using humor, I wrote The Elements of Stress … along with a love and admiration for The Elements of Style, which it parodies.

The other book is part of a series, The Ultimate Cartoon collection, and that was the result of a desire to showcase cartoons by my favorite cartoonists. This project began years ago with this being the third in the series. The cartoon world has become a ghost-town with so many venues for cartoonists, like Playboy, Harvard Business Review, Barron’s, MAD and others, now gone. My series, I contend, is one of the last places for the best work by the best cartoonists to be seen.

How long did it take to go from idea to publication? And did the idea change during the process?

The Ultimate Cartoon series was something that popped up in a phone call with my agent and not too long after that my agent found a home for the idea. This has become exactly what I imagined in my head except more beautiful than I could have imagined. But I did get everyone I dreamed of to contribute.

The Elements of Stress was initially to do more with E.B. White and maybe sex because Michael Shaw, the other writer, was inspired by E.B. White’s Is Sex Necessary? But really Michael just wanted to do a parody of an E.B. White book in some form. This first idea had no input from me except I brought to the table some book experience and advice. I asked around about that idea and quickly learned publishers were not going to touch it. As it kept getting rejected, I called an audible and suggested Elements of Strife thinking it should have something directly to do with what people were going through. That idea appealed to my agent.

As work began, we struggled making the book an easy read off of such a heavy concept. Shifting it from “Strife” to “Stress” make the book more digestible because the definition of stress was less loaded and we were no longer burdened with the baggage of defining the concept of strife.

Were there any surprises or learning moments in the publishing process for this title?

Publishing is nothing but surprises. The only common denominator with all books is that you always think the book is going to rock the publishing world. That’s just a small part of your thinking but an important elem

Publishing is nothing but surprises. The only common denominator with all books is that you always think the book is going to rock the publishing world. That’s just a small part of your thinking but an important element, that excitement, to fuel the project. There’s also always a larger part that is realistic and skeptical. I’ve learned not to get too high or too low and understand no one setback is going to make or break a book … or career.

Personally, the biggest problem I have is people moving on to something or somewhere else. There is so much movement in this business. One of my books had six different editors. Now that said, I love my two current publishers. I’ve loved all the people I’ve worked with but it was a big loss when we got separated. I’ve now had five different publishers.

Were there any surprises in the writing process for this book?

Writing about stress proved to be very stressful. But I am surprised by how sincerely useful the content in this handbook turned out to be. While writing it, real solutions to handling stress emerged from our research and our imagination. I wasn’t surprised by how inspirational the source of the parody, The Elements of Style, turned out to be. I’ve read those 90 pages over and over.

There were few surprises for the cartoon book. It went as smooth as I expected. I got thousands of submissions and the work chosen stood out and selections were a no brainer. I expected very high quality work and the book is hilarious cover to cover.

What do you hope readers will get out of your book?

It sounds cocky, but I’m not hoping, I’m confident readers are going to laugh and really enjoy both of these books. I have stacks of humor books creating a fortress around my bed, but I’m very proud of both of those books. But credit goes to all the talented cartoonists. I am hoping the reading public finds either of these titles out there. There’s about three million releases a year now so it’s tough. I think everyone in my family came out with a book.

If you could share one piece of advice with other authors, what would it be?

It’s hard to narrow it down to one bit of advice. I discuss many in my writing class and I’ve been given many more from my teachers. But if I had to choose only one … I was going to say not to write in their head. That’s a whole other thing. I would say write a funny premise, build funny characters and the jokes will unfold. Don’t write jokes and build a story around it.

One last one, I like to the highlight the strongest parts of a piece and then seriously consider cutting the other parts—not sure I did that here.

Bio: Bob Eckstein is a New York Times​ bestselling author, award-winning illustrator, and New Yorker cartoonist. He teaches writing and drawing at NYU and has two new books available now: All’s Fair in Love & War: The Ultimate Cartoon Book and The Elements of Stress and the Pursuit of Happy-ish in this Current Sh*tstorm.

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