The Most Experimental Caldecott Winners of All Time

Whilst gazing upon the lovely Caldecott Medal poster in our library the other day, I got to thinking: Which Caldecott Medal winning books pushed the envelope the most? Which were the most, I don’t know, experimental?

Since I’ve read all the Caldecott Medal winners, it seemed worth a try.

These were the books that stood out to me – disagree? Have one of your own? Let’s hear it in the comments¹.

¹My dream commenter on this post is KT Horning. Just putting it out there.

The Little House by Virginia Lee Burton

Caldecott Medal Year: 1943

Why is it experimental? The Notorious VLB was all, “Okay, I’m going to make a book where the main character is a house. A house. No, no – not HORSE. HOUSE. Do I have your attention? Now get this – the house won’t move for almost the entire book.” That’s bold, folks, and I think it probably surprised readers even more when it came out lo those many years ago.

Where the Wild Things Are by Maurice Sendak

Caldecott Medal Year: 1964

Why is it experimental? Maurey let his inner wild thing (hardy har) fly with this book. Not only did the story tick off prudish parents, but WTWTA remains the most well-known example of a picture book that used white space boarders to wordlessly convey setting and tone. Check out this post to see what I mean.

Black and White by David Macaulay

Caldecott Medal Year: 1991

Why is it experimental? This was the book that inspired this post. Have you read this book lately? Four seemingly separate stories (rendered in four different styles) slowly come together revealing a fifth. It’s so unusual I am surprised a committee all came together to give it the medal (and I’m thrilled they did).

Tuesday by David Wiesner

Caldecott Medal Year: 1992

Why is it experimental? You knew the Wies-man was going to be on this list. All the guy does is experiment (for more recent proof – check out the cat cam he invented for his book Mr. Wuffles!)

While Tuesday can’t quite be called wordless (It provides dates and times) It is the first Caldecott Medal winner with almost no words (Noah’s Arc by Peter Spier, the 1978 winner, had long wordless stretches, but I don’t think it claims the first wordless winner status). And if you think about it, the only other wordless (or nearly so) books in this category are Flotsam (also by Wiesner), The Lion and the Mouse by Jerry Pinkney, and A Ball for Daisy by Chris Raschka.

The Three Pigs by David Wiesner

Caldecott Medal Year: 2002

Why is it experimental? Wiesner was just getting warmed up with Tuesday. With The Three Pigs, Wiesner explodes the form, deconstructing a famous fable and showing readers that anything can happen within a picture book. There were meta picture books before The Three Pigs, but here’s guessing this book casts a large shadow over the the meta books we’re seeing today.

The Invention of Hugo Cabret by Brian Selznick

Caldecott Medal Year: 2008

Why is it experimental? Selznick mixed words and illustrations in a way that hadn’t quite been done before. When it came out, it stunned everyone. Just as experimental was the Caldecott committee who selected it, as it broke the Caldecott Medal mold. Hugo Cabret is the longest medal winner in history, as well as the first to have extended periods of just text.

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