Winnie-the-Pooh at 100: The real story behind EH Shepard and AA Milne's classic collaboration

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When illustrator Ernest Howard Shepard was working as a political cartoonist and illustrator for British satirical magazine Punch, one of his early drawings featured a small bear in a pile at a toy shop, explains Hollie Piff, project archivist of EH Shepard Collections at the University of Surrey. “He looks remarkably similar to Winnie-the-Pooh,” she says.

Shepard wouldn’t have known then that he would help bring to life one of the world’s most recognisable bears, who this year celebrates his centenary after first appearing in the 1926 children’s book Winnie-the-Pooh, written by AA Milne and illustrated by Shepard.

EV Lucas, who worked at Punch magazine (as did Milne), introduced the pair. “He saw that they would be a really good match for each other,” says Piff. “At the beginning, Milne was a little bit trepidatious about getting involved with Shepard. He wasn’t entirely convinced, but Shepard was very professional and clearly very talented, and Milne was immediately won over by his initial sketches. It started around the political Punch table and ended up with quite whimsical illustrations.”

One fan of those illustrations and stories is Her Majesty the Queen. She remembers playing Pooh sticks as a child and is introducing a special week of programmes on Radio 4 to mark Winnie-the-Pooh’s very special birthday. This week there are five new readings of the original stories from Sir Lenny Henry, Ambika Mod, Jim Broadbent, Toby Jones and Hayley Atwell. And next Saturday there’s a new play by Edward Kemp, which explores the involvement of Christopher Robin, Milne’s son, in the campaign to protect Ashdown Forest in East Sussex.

Shepard and Milne, who both served in the First World War, first collaborated on Milne’s children’s poetry book When We Were Very Young in 1924. That’s the year that Shepard produced what is considered the very first sketch of Winnie-the-Pooh, modelled from Christopher Robin’s toy, but he looks very different to the hug-gable, honey-loving bear he would become. “He looks much gruffer and he’s longer-limbed,” says Helen Roberts, archives and special collections manager at the University of Surrey. That’s why Shepard decided to use his son Graham’s toy bear Growler as his inspiration instead.

In a quote taken from Shepard’s unpublished manuscripts, he writes, “The bear that I used as my model belonged to my son. He was a wonderful bear, quite the best I have seen and seemed to have a character of his own. He lived long enough for my son to hand him on to his own child, my granddaughter, who when war broke out, was taken to Canada by her mother to grandparents there. Pooh [referring to Growler] went too, only to die at the hands, or teeth, of a neighbour’s dog.”

Alongside Winnie-the-Pooh, Christopher Robin’s Piglet, Eeyore, Kanga and Tigger toys also inspired Milne’s stories. He placed them in the fictional 100 Acre Wood, based on Ashdown Forest, near Hartfield. Cotchford Farm, just to the south west of the village, is where the Milnes lived, with the woods their playground.

The moral bases of the story – fun, friendship, learning – are timeless

“It was a happy task for me – making those drawings for the stories of Pooh and Piglet, Kanga and Eeyore, Owl and Tigger and I spent hours with the author going over the ground that was the scene of their adventures. I drew the pine trees, the house where Owl lived and Piglet’s home and watched Christopher Robin, aged about five, making mud pies in their garden at Hartfield with my son,” Shepard wrote. “I have grown to love the little folk of these stories; my heart particularly goes out to Eeyore – the gloom in which he wallows and his attitude to life as a whole makes him very human – indeed human characteristics are what we find in them all.”

And just like a human, Pooh slightly changes throughout time. “Christopher Robin’s walking him down the stairs and he’s very clearly an inanimate object,” says Piff. “But he’s a lot more organic-looking in the later drawings. Shepard drew from life. He really wanted everything to feel alive, and I think that Winnie-the-Poohvery much does.”

Milne and Shepard’s collaboration was revolutionary for the time – the text and illustrations interact seamlessly where one cannot exist without the other. Yet in 1927, Milne and Shepard released the poetry collection Now We Are Six, and in 1928, Winnie’s final story with The House at Pooh Corner. After that, Milne stopped writing children’s stories and that’s when Winnie-the-Pooh ended for him.

“I get the impression there was a connection between Milne and Christopher Robin [before the books], but it actually ended up being the short stories he created for his son that drove them apart, which is very sad,” says Roberts. “Christopher Robin didn’t have an easy time at school,” adds Piff. “He was bullied because they didn’t change his name in the books. Everyone knew exactly who he was and he couldn’t really hide.”

The world of Winnie-the-Pooh, to which he dedicated almost half his life, very much continued for Shepard. “He’d do Christmas cards, he drew Winnie-the-Pooh for friends and their children, and those pop up at auction every now and again, where someone has a letter with a little drawing on,” says Piff.

Shepard’s entire body of work spans more than 25,000 sketches and illustrations – as well as Winnie-the-Pooh, he also illustrated Kenneth Grahame’s The Wind in the Willows. “There is immense pride at being one of his descendants,” says Shepard’s great-great-granddaughter Bella Hunt. “His characterisation will live long beyond us. I would have loved to ask him: ‘If you’d known when you started sketching these characters they would be just as recognisable 100 years on, how would that have made you feel?’”

Few pieces of work can make the impact that Winnie-the-Pooh has – it’s never been out of print and has been translated into more than 70 languages, including Latin, enduring for new generations to discover. Shepard’s great-great-granddaughter Marina Campbell says, “The moral bases of the story – fun, friendship and learning – are timeless. Especially during times when the world feels very loud and often heavy, these are the kind of themes and stories we as humans gravitate towards.”