This year marks the 100th anniversary of the very first Winnie-the-Pooh book. In How a Bear Became a Book: The Collaboration That Created Winnie-the-Pooh, Annette Bay Pimentel and Faith Pray pay homage to the successful partnership between author A.A. Milne and illustrator E.H. Shepard that resulted in the beloved classics. Pimentel’s playful metafictional text and Pray’s whimsical multi-layered mixed media artwork simultaneously pull back the curtain on the publishing process itself. PW spoke with the creative team about finding a fitting narrative and artistic style for the book, the magical interaction that occurs between art and text in Milne and Shepard’s books, and the enduring appeal of Winnie-the-Pooh.

This book is as much about Winnie-the-Pooh as it is about how an idea becomes a book. Can you share the story of this project?

Annette Bay Pimentel: As a child, my experience of the Pooh books was very much tied to how the text interacted with the pictures. Basically, I didn’t get the jokes from the text, and it was the pictures that helped me understand what was going on. And so I wanted to write a picture book biography of E.H. Shepard. I had a very difficult time finding my way into the story, but I have a great critique group that kept asking me, “Well, what do you care about in this story?” The more I thought about it, the more I realized that it was that interaction between text and image. Then, through the research, it became clear that what was interesting to me about the story was the interaction between Milne and Shepard. In the text itself, the image of Winnie-the-Pooh becomes the symbol of that collaboration. It was nice to have a character who I love and who I think is very charmingly funny and innocent.

How did you decide to have Winnie-the-Pooh be a character commenting on the story and what was your approach to writing from his perspective?

The collaboration between Milne and Shepard was so magical at catching this vision of buoyancy and unfettered childhood. —Annette Bay Pimentel

Pimentel: I am always intrigued by books that cross boundaries. In the past, I had tried another metafictional nonfiction story that didn’t work out. I have a critique partner who was writing a metafictional picture book, and I was watching what she was doing as she showed me different revisions, and it occurred to me that I could try metafiction with this book—that I could have a character talk or push against the narrator, and then, through that interaction, reveal what happened historically. And Winnie-the-Pooh was the obvious choice, because he is the linchpin character in those novels. It was also a delight to go back through the novels and figure out how I could capture his voice without quoting. He has a very distinctive voice, and so that was really fun. I spent a lot of time going back and saying, “Okay, does he use contractions?” and things like that. It was fun to dive in that way.

Could you both speak to how your own collaborative approach was inspired by the relationship between Milne and Shepard?

Pimentel: I knew from the very beginning that the art was central to this because I saw it as Winnie-the-Pooh emerging. I had no idea how that would happen, but I thought, “Illustrators can do magic things.” It was actually first offered to another illustrator who came back and said, “Well, this is an unillustratable manuscript because you can’t have a character who keeps changing.” I was very worried, but Mark Podesta, our editor, told me, “No, this is just not the right illustrator for this project.” When I saw Faith’s initial sketches, I thought, “Oh, she’s figured it out.”

Faith Pray: I think it’s pretty fun that in our book we find out that A.A. Milne had different illustrators try out the text and see how they worked, and that I was the second person to get a try with this book. I knew that Annette had envisioned something coming out of words, and when I first read the text, I could already picture how I wanted it to go. Then it was just a matter of experimenting with mediums until I found the right ones that worked with what I wanted it to look like on the page. I wanted it to feel collaborative, and so I didn’t just want it to have words that looked like they were making a bear.

I also wanted to have handwriting, so I reached out to archives in Texas. They had some different letters and stories and art that was done by E.H. Shepard and A.A. Milne. They sent me a hundred pages of scans, and I also bought a reproduced, handwritten manuscript of A.A. Milne’s first Winnie-the-Pooh draft—the one that became the book. I used those and also my own childhood book. I scanned the lettering, printed it onto freezer paper, and then I did rubbings through a screen print, and I made them into the bear shape with a spoon rubbing the ink onto mulberry paper. I used almost a silk-screen print to create this speckled bear shape that gradually became more like the bear we wanted to see at the end.

Because there were layers to the story, I wanted to have four different mediums to give a different look for each layer. There was the layer with the words and there was the layer with the screen-printing bears. I used pencil and ink to be similar to how Shepard worked. I also used watercolor and colored pencil to bring in the modern aspect of the book. We had a little bit of back and forth through Mark and art director [Melisa Vuong]. Mark is a great connector of people and ideas, and so he was able to convey some of Annette’s ideas to me and show Annette what I had done to see if she was feeling okay with the historical aspects’ accuracy and also her vision for how it was going to be.

Why do you think the Winnie-the-Pooh books have had such an enduring appeal?

Pimentel: I’m convinced that it’s because the collaboration between Milne and Shepard was so magical at catching this vision of buoyancy and unfettered childhood. It was surprising and even shocking to me to see how other people tried to illustrate Winnie-the-Pooh. And I don’t think it would have endured. The text is beautiful and funny, but it really needs the art of Shepard, and there was just an alchemy there. I think it has to do with that vision of childhood.

Pray: Shepard’s work is so whimsical and playful, which is amazing, if you see some of his other work. When he was a soldier in war, he did wartime sketches, and he did editorial illustrations for Punch Magazine, so this work was so different from those, and it was fabulous to see how lighthearted and lively his characters are. And then Milne’s text is lyrical and really draws you in. But it’s the combination of both together, I think, that lightens your heart and makes you feel like you could be anybody. Your imagination gets to open up as you read each chapter.

How a Bear Became a Book: The Collaboration That Created Winnie-the-Pooh by Annette Bay Pimentel, illus. by Faith Pray. Holt, $19.99 Mar. 31 ISBN 978-1-250-35844-8