Interview with David Sherrin, author of BIG BAD WOLF’S YOM KIPPUR

In his new picture book BIG BAD WOLF’S YOM KIPPUR (Apples & Honey Press, 2023) illustrated by Martin Morón, author David Sherrin offers readers a fun, fractured fairytale that explores the essence of Yom Kippur in a meaningful and kid-friendly way. Full of heart and humor, readers will no doubt adore the cranky yet introspective Big Bad Wolf. The magical fairytale-like illustrations are a perfect pairing for the lively text. I’m delighted to welcome David and can’t wait to learn more about this terrific book.

Your new book, BIG BAD WOLF’S YOM KIPPUR, is a fractured fairytale with a Jewish twist. Can you tell me a bit about what inspired the story?

I really love fractured fairytales like Shrek and Wicked. I think I appreciate stories where there is some complexity to the villain or we find out the villain isn’t so terrible after all. A few years ago, I wrote a few separate stories without Jewish themes in which the Big Bad Wolf was misunderstood. I remember there was one in which he was an environmentally friendly, or green, architect. In that one, the real reason he was huffing and puffing at the Three Little Pigs’ houses was to test the strength of their homes and to suggest more environmentally sustainable materials like bales of straw. We can still see remnants of that original story in his interaction with the Three Little Pigs’ in Big Bad Wolf’s Yom Kippur. I was also writing a bunch of Jewish themed stories and getting some interest from Apples & Honey Press and at a certain point I recognized Wolf’s character and story arc would work perfectly with a Yom Kippur repentance and growth theme.

David Sherrin

While the story is playful and humorous, there is also an underlying theme of personal growth. Was it difficult to balance these elements in your writing?

Yes! I mean…how many fun and joyful Yom Kippur stories are there? But the fractured fairy tale element leads naturally to some humor and gave those opportunities. And obviously Jewish culture and storytelling is rife with humor even about difficult topics. So there was a lot to work with. I’m grateful to have had some incredible editors and a wonderful team at Apples & Honey so the manuscript underwent many drafts and significant transformations from the time they first saw it. Thankfully, they recognized and valued both the humor and the character arc of the story and helped me develop both aspects of Big Bad Wolf’s Yom Kippur.

Yom Kippur is not an easy holiday to write about for young readers. Why were you drawn to write about Yom Kippur?

Well, kids are constantly being asked to reflect and do better…probably much more frequently than adults. So I don’t think the ideas of saying sorry, personal growth, and forgiveness are foreign to them. They are dealing with them every day and sometimes multiple times a day. The goal I guess is to avoid too much emphasis on fasting and prayer, although both show up in the story, and instead emphasize the values of the holiday.

What were your thoughts when you first saw Martín Morón’s illustrations?

Illustrations can make or break a picture book, of course! Martin’s illustrations are masterful and I was blown away by them, especially since I can’t draw anything. It is mind boggling to me that anyone can picture scenes like that and depict them visually…but that is what makes picture books such an interesting team project. I’m pretty proud of the story itself but even prouder and happier if a reader comes away saying “wow, those illustrations are fantastic!” because then I know the book is a complete package and I hope readers appreciate the skill and care that Martin put into the illustrations. I’m so thrilled he will illustrate the sequel as well!

What do you hope your readers take away from BIG BAD WOLF’S YOM KIPPUR?

Picture books normally have two types of readers: the adults and the kids. And I think the best picture books have elements for both. Let’s say some twists and surprises and cleverness for the adult readers that leave them with a grin and some silliness and a great story for the kids. I hope readers, Jewish or not, come away thinking that a Jewish themed picture book can also be a great story in and of itself apart from its message. Non-Jewish readers hopefully get some knowledge and appreciation for this holiday that they might have heard of but don’t really know anything about. And I think just imagining what it would mean if these famous fairy tale characters were Jewish is really fun and thought-provoking for the Jewish reader, young or old. Lastly, of course, there’s the message itself…that we can grow, be better, and be kind no matter how hard that might seem sometimes.

Thank you, David!

David Sherrin is a national award-winning teacher at Scarsdale High School in Westchester. He is the author of the picture books Big Bad Wolf’s Yom Kippur and The Pirate Rabbi and the creator of the podcast Conversations in World History. David lives in Tarrytown and is the proud dad of three children. See more at

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