The Best Children’s Books Ever?: Our Top 10 Caldecott Medal Winners of All Time

By Noelle, Librarian Extraordinaire

The Randolph Caldecott Medal is given out every year in January to the best illustrated children’s book.  With the medal recently awarded, I thought it would be a good time to look at this prestigious award.

Caldecott Award

The Caldecott Medal has been given out for the last 74 years to the best illustrated children’s book.  However, the catch is that the illustrations have to be married successfully to the text.  So if you have a superbly illustrated book but the story is kind of meh, it won’t be winning anything.  The one other catch?  The illustrator has to be a resident of the United States (other countries have their own awards).  Outside of that, the winner can be a picture book or non-fiction.  Winners have been awarded to biographies and folktales, and once, amongst some controversy, to a novel (but if you’ve ever seen or read the Invention of Hugo Cabret which is the base for the Oscar-nominated film Hugo, you’ll understand the exception.  I may not agree with it, but I understand it).

UPDATE: Looking for more great children’s books? Make sure to read Our Top 10 Newbery Award Winners of All Time.

But, like anything else, all books are not created equal.  Sometimes the titles to choose from in a given year may simply be a weak field.  It happens.  Another item to be aware of is that this is basically an art award.  Not everyone has the same taste in art, and what may be attractive to you may not be attractive to someone else.

Now how are you, the parent, to choose the best of the Caldecott Medal books to share with your children?

I’m Here to Help!

I’ve read all of the Caldecotts and have my own criteria.  My criteria is that the book has to be not only cool in its illustrations, but it has to be a story that I can share easily.  As a librarian, being able to read something aloud with children in a group is always something that gives a book that extra something special.  My top 10, then, are heavily skewed towards books that are great to share one-on-one or with a larger group.  They are all fabulous stories with great illustrations.  I hope you agree!

With no further ado…

My Top 10 Caldecott Medal Winners (in no particular order):

Where the Wild Things Are

1. Where the Wild Things Are written and illustrated by Maurice Sendak.  Winner in 1964.  I think this is probably the epitome of a perfect book.  Unique illustrations and lyrical text that rolls off the tongue and burns into your memory. “The night that Max wore his wolf suit and made mischief of one kind and another…” The book is so memorable, there are dolls and  there was even a (kind of odd) movie made of it.  I strongly urge open-minded folks to check out Sendak’s recent 2-part interview with Stephen Colbert.  While you may never look at Where the Wild Things Are the same again, you’ll also laugh so hard your stomach will hurt.  Sendak has many other remarkable books, but my next favorite of his is Pierre.

Kitten's First Moon

2. Kitten’s First Full Moon written and illustrated by Kevin Henkes. Winner in 2005.  Henkes has written countless books mainly starring mice, such as Chrysanthemum, Owen and Lilly’s Purple Plastic Purse.  He had won a Caldecott Honor before, but he changed styles to write Kitten’s First Full Moon, favoring thick lines and black and white over colors and small details.  The result is a fantastic simple story of a kitten trying to get to the moon because she thinks it is a bowl of milk in the sky…and she wanted it.  Henkes has stuck with his new style of illustration and simple storytelling, scoring new hits with the likes of Old Bear and Little White Rabbit, so readers get a choice of art style and story and both are fabulous.


3. Officer Buckle and Gloria written and illustrated by Peggy Rathmann. Winner in 1996.  I absolutely love this story of a police dog named Gloria who–behind the back of Officer Buckle–acts out his safety tips as he imparts them to students.  Suddenly, Officer Buckle’s safety speech is in high demand and he doesn’t realize it is really due to Gloria’s antics…until he does.  Not only is the story terrific (and a personal huge favorite of mine), but the little details in the illustrations are laugh out loud funny.    Rathmann also penned another favorite story of mine, the nearly wordless Good Night, Gorilla.


4. Tuesday written and illustrated by David Wiesner. Winner in 1992.  Wiesner is a guy who thinks outside of the box and reading any picture book by him is like stepping into someone else’s dream.  One Tuesday evening, frogs suddenly are able to fly on their lily pads and they take a trip to town, getting into all sorts of trouble.  It is   a wonderful journey and it is wordless except for the very beginning and very end.  Wiesner also wrote a couple of other award winners: Flotsam and The Three Pigs.  I like those, too, but Tuesday still wins my vote for his best.

The Snowy day

5. The Snowy Day written and illustrated by Ezra Jack Keats. Winner in 1963.  Keats is famous for writing picture books that not only starred children of other ethnicities, but were also based in urban settings.  His style is unique.  The Snowy Day follows a boy named Peter as he has typical winter adventures out in the snow-covered city.  The text isn’t poetry, but it is close and there’s just something a little bit magical about it, as there is in a very snowy day.  One of my other favorites of Keats is Whistle for Willie, also starring Peter.

Make Way for Ducklings

6. Make Way for Ducklings written and illustrated by Robert McCloskey. Winner in 1942.  I may be a bit prejuidiced because I am a Boston girl, but there is just something about this duck family and their traffic-stopping journey to bring their ducklings through the city of Boston to the Public Gardens, where they can follow the Swan Boats and get treats.  McCloskey was from Maine, but he studied ducks in detail and sketched the Boston skyline just right.  Today, visitors flock to Boston to pose with the duckling statues in the Public Gardens, ride the Swan Boats (although they discourage feeding the wild fowl now) and you can even take the same walk the ducklings did through the streets. How many picture books published 70 years ago can you say have been THAT inspiring?   McCloskey also wrote the award-winning Time of Wonder.

Sylvester and the Magic Pebble

7. Sylvester and the Magic Pebble written and illustrated by William Steig. Winner in 1970.  Sylvester the donkey finds a red pebble that turns out to be able to grant wishes. Which is pretty cool and that could be the whole story, but when a lion prowls nearby, a panicked Sylvester wishes himself into a stone to hide, and can’t change back (how can a rock hold a pebble?).  Luckily, his bereaved parents end up saving the day (unintentionally) and like Dorothy in the Wizard of Oz, Sylvester learns everything he wanted could be found in his own backyard.  Steig also wrote many other excellent stories, including another favorite, Doctor DeSoto, as well as Brave Irene, Potch and Polly and countless others.

The Polar Express

8. The Polar Express written and illustrated by Chris Van Allsburg. Winner in 1986.  If you haven’t heard of the Polar Express, you must have been hiding under a rock.  It’s been a successful film (which has little to do with the book, but then how do you make 32 pages turn into 90 or more minutes of movie?) and has become one of the penultimate Christmas stories.  After all, what can be better at Christmas than a boy magically taken by train to the North Pole to see the big man himself?  And he brings back a bell from the sleigh which only true believers in Santa can hear.  All around the country, different communities have a “Polar Express” train ride you can take at Christmas, which usually includes hot chocolate and a visit from Santa.  The book is beautifully illustrated (of course) and has been exerting its magical holiday hold over children ever since its publication.  Probably one of the most popular Caldecott winners ever.  Van Allsburg also won for Jumanji (also made into a major motion picture), and has many other mind-boggling titles to his credit, including The Mysteries of Harris Burdick and The Sweetest Fig.


9. Rapunzel written and illustrated by Paul O. Zelinsky. Winner in 1998.  Where many other illustrators draw, Zelinsky paints.  And he does so gorgeously.  His retelling of Rapunzel is beautiful to say the least, and he does not shy away from the darker side of the fairy tale.  It is just one of those books that glows.  Equally fantastic is his Caldecott Honor titles, Rumpelstiltskin and Swamp Angel, both big favorites of mine.

Lon Po Po

10. Lon Po Po written and illustrated by Ed Young. Winner in 1990.  The story is the Chinese version of Red Riding Hood, where 3 children left alone at home have the wolf visit, pretending to be their Po Po (grandmother).  When the eldest realizes their trouble, the siblings must find a clever way to outwit the wolf and get to safety.  The illustrations feel like they almost bleed off the pages, both focused and unfocused, able to communicate the malicious intent of the wolf.  It is great to have a Red Riding Hood story where the kids have some backbone and also well worthwhile to be able to introduce children to the fact that fairy tales exist in all countries and that interestingly, the same ones repeat no matter where you go.  If you really want to have fun, look for every version of Cinderella you can find.  You’ll find Chinese, Japanese, Persian, Middle Eastern, Native American and more versions of the fairy tale.  Young has written numerous children’s books, including Mouse Match, Seven Blind Mice and many more.

And There You Have It!

I’ll admit I had to struggle at the end for there are a few others I think also worthy of particular notice, including Paul Goble’s Girl Who Loved Wild Horses and May I Bring a Friend? by Beatrice deRegniers.  But as new books win the award every year, perhaps I shall have to revise my list.

I am firmly of the belief that you are never too old for picture books.  In fact, I believe picture books are one of the hardest types of books to write successfully (despite every celebrity trying to publish one) and are also an art form because every page is thought through.  How much text per page, which words, the font, the placement of it, fitting the illustrations to the page, the point of view, the way the illustrations are created are all just a few of the factors that go into putting a picture book together.  You can clearly see the difference in award winners like these titles if you look around enough.  And since we never grow too old for art (do we?), keep sharing picture books no matter what your age.  You won’t regret it.  However, if you have kids who are mainly past the point of picture books, then check out my Top 10 list of Newbery Award winners.

And This Year’s Winner is….

A Ball for Daisy

This year’s winner of the Caldecott Medal is A Ball for Daisy written and illustrated by Chris Raschka.  It is a very good book about a dog and a ball (how can you lose with that?) and Raschka has written many other solid books, most often very simply told, including Yo! Yes? and my favorite, Charlie Parker Played Be Bop.

You can see the full list of Caldecott winners and Newbery winners at the American Library Association’s website at  Click on the Awards and Grants link to see not only these awards, but many others for all different kinds of categories.  Enjoy and happy reading!

NoelleNoelle has been a children’s librarian for over 15 years. She’s also been a student teacher, worked as an online account manager, worked in a pet shop and as a supermarket checkout clerk, and as a dishwasher and fry cook. She is the proud mom of a beautiful daughter. You can read more of Noelle’s book reviews at Rave Reviews Log

Noelle can be reached at “Noelle @ DadDoes.Com”

Have a Question/Comment? Let Us Know!

Click Here For our Disclosure Policy