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The Art of Winnie the Pooh: Ernest Howard Shepard's Illustrations for the Classic Tale

Ernest Howard Shepard, also known as E.H. Shepard, was a British artist and illustrator best known for his drawings of Winnie-the-Pooh and the other characters from A.A. Milne’s classic children’s books. Shepard’s illustrations were first published in 1926 and have become an iconic representation of the beloved characters.

Shepard’s illustrations of Winnie-the-Pooh and his friends, Piglet, Eeyore, Tigger, and Kanga, were characterized by their simple, clean lines and expressive, cartoon-like style. He drew the characters in a way that was both childlike and sophisticated, capturing the innocence and wonder of childhood while also conveying a sense of humor and playfulness.

Shepard’s illustrations were also noted for their attention to detail and realism. He took great care to depict the characters and their surroundings in a way that was true to life while also adding his unique artistic vision. For example, his illustrations of the Hundred Acre Wood, where Pooh and his friends live, were based on the real-life Ashdown Forest in Sussex, England, where A.A. Milne lived and wrote the Pooh stories.

Shepard’s illustrations of Winnie-the-Pooh and the other characters have become an enduring symbol of childhood and have been widely reproduced in books, toys, and other merchandise. Shepard’s illustrations are considered an essential part of the legacy of A.A. Milne’s classic stories. They have helped to make Winnie-the-Pooh one of the most beloved and recognizable children’s characters of all time.

In addition to his illustrations for Winnie-the-Pooh, Shepard also illustrated other books, including “The Wind in the Willows” by Kenneth Grahame, “When We Were Very Young” and “Now We Are Six” by A.A. Milne, and many more. He was also an accomplished landscape artist and had exhibitions of his works in London. He was awarded the Order of Merit in 1976 and passed away in 1976.

#1 Then they went on to Kanga’s house, holding on to each other

Then they went on to Kanga’s house, holding on to each other

This original illustration was reproduced on page 129 of The House at Pooh Corner and is from the chapter in which Piglet does a very grand thing. It shows Pooh and Piglet walking against the wind on the way to Kanga’s house.

#3 He nodded and went out …and in a moment I heard Winnie-the-Pooh bump, bump, bump – going up the stairs behind him.

He nodded and went out …and in a moment I heard Winnie-the-Pooh bump, bump, bump – going up the stairs behind him.

This original illustration is reproduced on page 159 of Winnie-the-Pooh and comprises a full-page illustration in the published volume. It represents one of the iconic images of Winnie-the-Pooh and comes from the final chapter in which Christopher Robin gives a Pooh party, and we say good-bye.

#4 What do you see there, Tracks, said Piglet. “Paw-marks…”

What do you see there, Tracks, said Piglet. “Paw-marks…”

This original illustration is reproduced on page 34 of Winnie-the-Pooh from the chapter in which Pooh and Piglet go hunting and nearly catch a woozle. This is the first drawing in the sequence of hunting illustrations.

#5 What? said Piglet, with a jump.

What? said Piglet, with a jump.

This original illustration is reproduced on page 37 of Winnie-the-Pooh. It is from the chapter in which Pooh and Piglet go hunting and nearly catch a woozle. It is the third drawing in the sequence of hunting illustrations.

#7 This illustration of Eeyore with holly, Pooh with a jar of honey and Piglet with a Christmas cracker comprises the original illustration for the only known Christmas card

#8 Do You See Piglet? Look At Their Tracks!

Do You See Piglet? Look At Their Tracks!

This original illustration is reproduced (at a different angle to the original) on page 38 of Winnie-the-Pooh. It is from the chapter in which Pooh and Piglet go hunting and nearly catch a woozle. It is the fourth and final drawing in the sequence of hunting illustrations.

#9 There was a little left at the very bottom of the jar,and he pushed his head right in

There was a little left at the very bottom of the jar,and he pushed his head right in

This original illustration is reproduced on page 64 of Winnie-the-Pooh. It is from the chapter in which Piglet meets a Heffalump. The reverse of the drawing includes a note that this drawing was given by Shepard’s daughter as a gift in 1974.

#10 With these few words he went on tracking, and Piglet,after watching him for a minute or two, ran after him

With these few words he went on tracking, and Piglet,after watching him for a minute or two, ran after him

This original illustration is reproduced on page 35 of Winnie-the-Pooh and comprises a full-page illustration in the published volume. It is from the chapter in which Pooh and Piglet go hunting and nearly catch a woozle. It is the second drawing in the sequence of hunting illustrations.

#11 Christopher Robin finished the mouthful he was eating and said carelessly

Christopher Robin finished the mouthful he was eating and said carelessly

This original illustration is reproduced on page 55 of Winnie-the-Pooh. It is from the chapter in which Piglet meets a Heffalump.

#12 I’m not throwing it, I’m dropping it Eeyore

I’m not throwing it, I’m dropping it Eeyore

Pooh had got the biggest stone he could carry, and was leaning over the bridge, holding it in his paws. This original illustration was reproduced on page 98 of The House at Pooh Corner and is from the chapter in which Pooh invents the game of Poohsticks. At this point Eeyore had fallen into the river and Pooh, Piglet and Rabbit were attempting to make waves to wash him to the bank.

#13 Just the house for owl. Don’t you think so, little Piglet

#14 Lucky we know the forest so well or we might get lost.

#15 Piglet gets ready for the party.

Piglet gets ready for the party.

This Shepard drawing is a later version of that reproduced on page 149 of Winnie-the-Pooh from the final chapter of the book in which Christopher Robin gives a Pooh party.

#17 The Bathmat Christopher Robin gave a deep sigh… At the door he turned and said, “Coming to see me have my bath?”

#22 “Pooh!” he cried. There’s something climbing up your back.

“Pooh!” he cried. There’s something climbing up your back.

These original illustrations are reproduced on pages 52 and 47 respectively of The House at Pooh Corner. They both come from the chapter in which a search for Small is ‘organdized’

#23 And when Christopher Robin had nailed it on in its right place again, Eeyore frisked about the forest

And when Christopher Robin had nailed it on in its right place again, Eeyore frisked about the forest

This original illustration is reproduced on page 52 of Winnie-the-Pooh. It is from the chapter in which Eeyore loses a tail and Pooh finds one.

#24 Tailpiece illustration to AA Milne’s ‘Wind on the Hill

#25 As soon as he got home, he went to the larder; and he stood on a chair, and took down a very large jar of honey from the top shelf.

As soon as he got home, he went to the larder; and he stood on a chair, and took down a very large jar of honey from the top shelf.

These preparatory sketches reveal Shepard’s typical working practice with the reverse of the leaf prepared with pencil rubbing for transfer of outlines. The images show some heavy pencil markings where Shepard has heavily pressed down on his pencil for the process. The images are early since the spelling of Hunny has not yet been adopted within the illustration.

#26 Winnie-the-Pooh lived in a forest all by himself under the name of Sanders.“What does ‘under the name’ mean? asked Christopher Robin. It means he had the name over the door in gold letters, and lived under it…

Winnie-the-Pooh lived in a forest all by himself under the name of Sanders.“What does ‘under the name’ mean? asked Christopher Robin. It means he had the name over the door in gold letters, and lived under it…

“This original illustration is reproduced on page 3 of Winnie-the-Pooh and therefore accompanies the chapter in which Winnie-the-Pooh is first introduced.”

#28 There was a little left at the very bottom of the jar,and he pushed his head right in

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Written by Jacob Aberto

Sincere, friendly, curious, ambitious, enthusiast. I'm a content crafter and social media expert. I love Classic Movies because their dialogue, scenery and stories are awesome.

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