A. A. Milne hoped for immortality. In Winnie-the-Pooh, he found it

Imagine, for a moment, that you have travelled back in time to an evening in 1923. A man who would not look out of place in one of Sidney Paget’s ‘Sherlock Holmes’ illustrations has paused on the landing of his London house and is looking up at the open nursery door. Out in the world he is known for being reserved, even chilly, but, as he watches his young son saying his prayers, a much softer side of his character is clearly visible. There is a chaise in the corner of the nursery and lying on it is a teddy bear — a much-loved birthday present from the Harrods toy department.

Now imagine that, some 40 miles away, in the Surrey village of Shamley Green, another man is walking up the lane to the cottage he shares with his wife and children. He is worn out after a long day in the London office of Punch magazine, but he is whistling something cheerful; he is that sort of person. The lamps have been lit at home and, as he pushes open the gate, he smiles as he spots a small, rotund silhouette on an upstairs windowsill: the toy bear that his 16-year-old son has outgrown, but cannot bring himself to part with.

Alan Milne and Ernest Shepard, as they were then known, had both carved out impressive niches for themselves by the early 1920s. Milne’s effervescent plays were the toast of London and New York; Shepard’s witty cartoons were instrumental to Punch’s popularity. Yet, within a few years, their names would forever be associated with that of a honey-loving little bear: Winnie-the-Pooh. A global superstar — at last count, he has been translated into 72 languages — he is this month celebrating the centenary of his first appearance in a book.

‘The fact that 100 years later we’re still calling people an Eeyore or a Tigger is a testament to Milne’s characterisation and Shepard’s artistry,’ notes James Campbell, author of The Men Who Created Winnie-the-Pooh (Michael O’Mara Books, £25). After marrying into the family — his wife is the artist’s great-granddaughter — he has spent years piecing together the story of an unlikely pair, both greatly affected by the First World War, who together made a new and enduring kind of magic.

Someone intimately familiar with this is Jane Riordan, the writer entrusted with Milne’s legacy and the author of A Little Boy And His Bear, a brand-new collection of Winnie-the-Pooh stories (Farshore, £20) with illustrations by Andrew Grey that channel Shepard’s. ‘I don’t remember a time when I didn’t know the books, but every time I re-read them I find something completely new or a joke I missed when I was younger,’ she says.

Unlike his creation, A. A. Milne was a Bear of Very Great Brain. Born in 1882, he was taught by H. G. Wells at the north London prep school his parents ran and, after going up to Cambridge, got to know future Bloomsburyites such as Lytton Strachey and Leonard Woolf. He became the editor of Granta, the university’s literary journal, and then joined the staff of Punch in 1906 (after being turned down by Country Life, to whom, he later remembered, he had emphasised ‘my games record… and my early collections of birds’ eggs and butterflies’).

Not given to what Eeyore would later call ‘gaiety, song-and-dance, here we go round the mulberry bush’, he was married late to Daphne de Sélincourt, the gregarious goddaughter of Punch’s editor. He gained a well-run home, she an escape from the spinsterhood for which so many women of her generation were destined, but it was a pragmatic match that became increasingly distant.

A pacifist (to the dismay of his conservative seniors at Punch), Milne nevertheless was commissioned into the Warwickshire Regiment in 1915 and experienced the horrors of the Somme before trench fever sent him home to work in propaganda. He took a small toy-dog mascot out to France with him: Carmen, who has since found her way to the Hundred Acre Wood in Riordan’s work. The post-war years were brightened by the arrival, in 1920, of a longed-for son, Christopher Robin, and making a home on Mallord Street in Chelsea, where Augustus John was a neighbour. Still, he was restless. ‘I suppose that every one of us hopes secretly for immortality,’ he later admitted.

Shepard was born in 1879 in St John’s Wood, into an artistic family, but his happy childhood ended abruptly in his 10th year when his mother died. His father fell into a decline, finances became precarious and the young Ernest had to grow up fast (he was especially fond of go-getting Piglet, keeping a set of drawings in his studio for the rest of his life). In 1904, he married a fellow Royal Academy Schools student, Florence Chaplin, and the pair — known as Kipper and Pie — settled down to a modest, but contented existence as working artists in rural Surrey.

His life might have looked bohemian, but Shepard was unambiguously in favour of military action against Germany in 1914 and became an officer in the Royal Artillery, experiencing several very near misses. He continued sketching, sometimes on behalf of military intelligence. ‘His earlier work was very heavily hatched, much more static, but during the war he simply didn’t have the time,’ explains Campbell. ‘He had to go faster, so his style changed — he was using fewer lines, but making them work better.’ It was an evolution born of grim necessity, but it would help him bring the Hundred Acre Wood vividly to life.

The world’s most famous bear made his print debut without a name on February 13, 1924, in an illustration alongside Teddy Bear, a Milne poem printed in Punch before being published by Methuen as part of the collection When We Were Very Young. E. V. Lucas, Methuen’s chairman, matchmade Milne and Shepard for the project: he had a hunch that Shepard’s easygoing demeanour would make him an excellent foil for the introspective, occasionally prickly Milne.

Things got off to a bumpy start. After sending him several poems and approving the sketches Shepard produced, Milne invited him to Chelsea to sketch him reading to Christopher Robin. The door was answered by the parlourmaid who, acting on the instructions of the ever socially conscious Daphne Milne, asked Shepard to use the tradesmen’s entrance. Shepard politely refused, went home and wrote to Milne to explain why he had left. From then on, he always used the front door and their partnership was an equal one. ‘The way they worked was unique at that point in time, as far as we know,’ believes Campbell. ‘Never before had a writer and an illustrator been around the same table saying “a bit more of this, a bit less of that”.’

The poems were well received by Punch readers, but Methuen published them without special fanfare in November 1924. Yet the initial print run sold out on the first day and, by the end of the year, more than 50,000 copies had flown off the shelves in the UK and USA. After a shattering war and the Spanish Flu pandemic, readers were longing for light, joy and freedom — Milne’s words and Shepard’s pictures transported them to the safety of their own recollected childhoods, sunny days spent wandering ‘down to the wood where the blue-bells grow’ and daydreaming by the sea.

The duo, together with the real Christopher Robin, became celebrities and a sequel was inevitable. This time, the setting would be Ashdown Forest in East Sussex, where the Milnes had recently bought a weekend home, Cotchford Farm (later the home of the Rolling Stones’s Brian Jones). The focus, too, would shift to the world Milne had been building in bedtime stories for his son, at the heart of which was the Harrods bear formerly known as Edward, but now named Winnie after a real one at London Zoo (the ‘Pooh’ suffix was borrowed from Christopher Robin’s word for swans).

Never a great one for whimsy in his everyday life, Milne revelled in the silliness and jokes. ‘I think for him it was an escape of sorts and it became one for his readers,’ observes Riordan. Guileless and stout-hearted, Pooh is fond of the existential musings that are such a feature of young children’s conversation; today, you can buy a book of his philosophy, The Tao of Pooh.

Up to 150 community libraries housed in former red phone boxes can receive free copies of the original Winnie-the-Pooh stories and the new authorised sequel, A Little Boy and His Bear written by Jane Riordan.

The campaign supports the National Year of Reading and launched on Tuesday (October 6^th) in Canterbury, with Sally Phillips reading to local schoolchildren, alongside author of sequel Jane Riordan and illustrator Andrew Grey.

Anyone who has adapted a phone box can apply to receive copies by clicking here.

Shepard travelled regularly from Surrey with his sketchbook to sit down with Milne, draw Christopher Robin, his collection of soft toys (which by now included a forlorn donkey and a kangaroo) and Ashdown Forest itself. He wandered among its 6,500-acre patchwork of heathery heath, fern-carpeted valleys criss-crossed by streams and ancient deci-duous trees, sketching as he went. Back in his garden studio, he worked in details from photographs of his own son, Graham, as a little boy and Graham’s portly bear Growler, from whom he borrowed Pooh’s ‘tub’.

What emerged was a kind of Eden, which at first glance might seem to have little to do with the Roaring Twenties, but nods to the decade’s Devil-may-care spirit. ‘There are no worries beyond perhaps getting lost in the mist and there’s never a bedtime because it’s always time for elevenses,’ says Riordan. With his scruffy smock and unruly hair, Shepard’s Christopher Robin was refreshingly unlike the cherubic, rather chocolate-boxy children drawn by contemporary artists such as Lilian Hocknell.

His Hundred Acre Wood, meanwhile, was untouched by recent history, like the England Philip Larkin would later conjure in his 1914-set poem MCMXIV, the ‘place-names all hazed over/With flowering grasses’.

Winnie-The-Pooh was published on October 14, 1926, to universal acclaim. Readers of all ages fell in love with Pooh’s gentle humour and, in a world in which moving pictures were scarce, they were entranced by the dynamic imagery. Country Life called the book a ‘lovely portrait’, running Shepard illustrations alongside its review and following it with a tongue-in-cheek piece on Woozle Hunting in its December 4 issue. The book was serialised in the Daily Express and the Evening News and by the end of the year, hundreds of thousands of copies had sold. These were usually read aloud, as they still are today. ‘It’s an integral part of them: because Milne was a playwright, he really understood pacing and how conversation works,’ explains Riordan. ‘It’s something I’m very mindful of writing my new stories — my poor family do have to listen to a lot!’

Now We Are Six, the 1927 return to the Hundred Acre Wood, acknowledged the passage of time by giving Christopher Robin a human friend in the form of Anne, yet ended with his wish to remain ‘six now for ever and ever’. His real-life equivalent would soon be making the uncomfortable transition from child star to public schoolboy: Christopher Milne was mercilessly bullied for the promotional activities in which his mother had involved him, souring his relationship with his parents.

Milne’s wish had come true: by the late 1920s, he was one of the country’s bestselling authors, shoulder to shoulder with the likes of H. G. Wells, J. M. Barrie and Noël Coward. Yet, as did Sir Arthur Conan Doyle, he came to resent his creation, seeing Pooh as a distraction from his work for adults. Shepard, meanwhile, was grieving after the sudden death of his wife in 1927. The House at Pooh Corner, which came out in October 1928, was to be their final Winnie-the-Pooh book, they decided. They left readers two further lasting gifts: Tigger, bouncy paw eternally raised, and the game of Pooh Sticks.

Yet their partnership endured, with Shepard even illustrating Milne’s Year In, Year Out (1952), his final book. He wrote prolifically for adults, as well as publishing two autobiographies, although Pooh would always define him, to his chagrin. ‘He never really thought of himself as a children’s author,’ points out Riordan. The inhabitants of the Hundred Acre Wood continued to call on Shepard’s services as new colour editions were printed, but he never fell out of love with them: a 1970 colour sketch entitled ‘Part of a Pooh Orchestra’ shows Eeyore entangled in a tuba as Piglet saws away enthusiastically at a cello.

Milne died at Cotchford Farm in 1956, leaving part of the rights to his literary estate to the Royal Literary Fund, which continues to support authors through them. He is commemorated alongside Shepard by a plaque at Gill’s Lap (called Galleon’s Lap by Milne), Ashdown Forest’s highest point. This was unveiled in 1979 by Christopher Milne himself, who, later in life, after opening a bookshop and becoming a writer himself, reached an understanding with Pooh. The children who visited then are now bringing their own children to the same place to soak up its magic.

Riordan spends a lot of time in the forest seeking out inspiration, following in Pooh’s paw-prints. ‘You really feel as if you’re stepping into one of the illustrations every time you go there,’ she says. ‘It’s changed, of course, but it’s still so familiar from the books.’ Thanks to A. A. Milne and E. H. Shepard, it will forever be an enchanted place where a boy and his bear play.

Winnie-the-Pooh: A Little Boy and His Bear by Jane Riordan and illustrated by Andrew Gray, is out now

The Men Who Created Winnie the Pooh by James Campbell, published by Michael O’Mara Books, is out now

This article first appeared in the October 7 issue of Country Life. For more information on how to subscribe, click here.