The Tail Of Eeyore

The Tail Of Eeyore

Illustrator E.H. Shepard's drawings of A.A. Milne's notoriously glum Eeyore have charmed generations of children, around the world. As Sotheby's presents two very special examples of Shepard's drawings of the doleful donkey, award-winning children's author Nadia Shireen reflects on the character's enduring appeal in the hearts of millions of Milneans.
Illustrator E.H. Shepard's drawings of A.A. Milne's notoriously glum Eeyore have charmed generations of children, around the world. As Sotheby's presents two very special examples of Shepard's drawings of the doleful donkey, award-winning children's author Nadia Shireen reflects on the character's enduring appeal in the hearts of millions of Milneans.

I t is a curious failing of grownups that we presume children are only interested in happiness. We scrabble to shield them from depictions of sorrow and ennui, hoping that by doing so, our children may never be troubled by these – annoyingly inevitable – emotions.

But kids are clever. They know when grownups are hiding something; which perhaps explains the timeless appeal of Eeyore. The most doleful donkey in children's literature can usually be found in the south east corner of Hundred Acre Wood, munching upon thistles. Not for him the stout optimism of Winnie-the-Pooh, nor Tigger's manic joy. Eeyore is of a permanently gloomy disposition. But generations of children love him just the same, perhaps recognising the honesty of his unvarnished outlook, even when his pessimism is so relentless it becomes delightfully comical. And, as we can see in the two lots included in Sotheby’s July Books & Manuscripts sale, these traits are perfectly illustrated in the spare yet expressive line of E.H. Shepard.

E.H. Shepard The Tail is Lost (four original illustrations) [1926] ESTIMATE: 60,000 - 80,000GBP

After first collaborating on the poetry collection When We Were Very Young (1924), it was Shepard who encouraged fellow Punch staffer A.A. Milne to look to his son’s toy collection as inspiration for the cast of characters we eventually meet in Winnie-The-Pooh (1926). Just as Shepard carefully studied Ashdown Forest near Milne’s home in East Sussex to inform his drawings of Hundred Acre Wood, his exceptional observational drawing skills were used to great effect when it came to breathing life into Christopher Robin Milne’s stuffed animals.

Among the menagerie was a toy donkey, so well-loved its head had started to sag and droop forwards. It was this posture which suggested Eeyore’s baleful character to Milne, and which Shepard perfectly captures in the sequence of images The Tail Is Lost. Eeyore cranes his neck this way and that, hoping for a glimpse of his beloved tail. It simply isn’t there. “Somebody must have taken it,” decides Eeyore. “How Like Them.”

'Even now it is difficult not to pause on these pages to quickly check that one’s own tail is firmly in place...'

One of the most engaging qualities of these illustrations is the mysterious way in which Eeyore’s sluggish contortions also suggest the unguarded movements of a small child; indeed, even now it is difficult not to pause on these pages to quickly check that one’s own tail is firmly in place. More broadly, Shepard is a master at perfectly marrying the fantastical with such a sense of place and realism that we believe and accept these characters wholeheartedly. We can feel the twigs snap beneath our feet as we wend our way through Hundred Acre Wood, and we can feel the protective love of Christopher Robin as we see him pinning Eeyore’s tail back in place. (It was Pooh who found it, of course – Owl was using it as a bell-pull.)

Those of us who make books for children are always chasing an elusive magic. We long to achieve the delicate balance of word and image, but we are also always trying to make space for the soul of the reader; for only then can any story truly come alive. It was a magic that seemed to come naturally to Shepard and Milne, and one which happily, we can revisit again and again at the turn of a page. For now, let us stroll to the south eastern corner of Hundred Acre Wood, where we will find a house made of sticks, some clumps of chewed thistle, and, with any luck, a donkey called Eeyore, happily reunited with his tail.

E.H. Shepard When Christopher Robin had nailed it on... (Original illustration) [1926] ESTIMATE: 70,000-90,000GBP

“Eeyore frisked about the forest, waving his tail so happily that Winnie-the-Pooh came over all funny, and had to hurry home for a little snack of something to sustain him.”

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