E.H. Shepard - Drawing Winnie The Pooh


Ernest Shepard, the man who drew Pooh, is now almost as famous as the bear of little brain’s creator, A.A. Milne. Shepard began illustrating Milne’s work in 1924 for the first edition of his poems, ‘When we were Very Young’. In fact Milne had not been sure that the ‘Punch’ artist had the right style for his first books and was a little hesitant to give Shepard the job. The pair travelled down to Ashford Forest in Sussex to meet the real-life Christopher Robin and see the countryside which had inspired many of the stories and poems. After seeing Shepard’s drawings from the trip and his interpretation of Winnie the Pooh and the other characters from his early poems he decided that Shepard would be the right choice after all. Shepard went on to illustrate all of A.A. Milne’s books for children and the winning combination has gone on to enchant both children and adults for almost 80 years.

Ernest Shepard was born in London in 1879 and encouraged by his mother to draw from a young age. He studied at the Royal Academy and sold his first work to illustrated papers before beginning a successful career as a cartoonist for ‘Punch’. Word War I intervened and Shepard served in France, Belgium and Italy, reaching the rank of Major and continuing to do sketches and illustrations of life on the Front. When he returned in 1918 his agent had the idea that he should try illustrating children books and it was around this time that he met AA Milne. The pair could have had no idea of how phenomenally successful their partnership would be. It gained both men an international reputation and a significant amount of money. It was in 1969, shortly before he lost his sight, when Shepard did his last work for Winnie the Pooh. He died in 1976.

Shepard’s pencil and pen and ink drawings are highly regarded and sought after by both collectors and lovers of the Winnie the Pooh stories. In the last ten years original E.H. Shepard drawings have realised record prices. In 1998 Sotheby’s sold ‘Tiggers can’t climb trees’, the famous drawing of Tigger falling out of the tree, for £20,900 ($34,000) and a signed pen and ink drawing of Pooh and his honey pot for £11,500 ($18,400). The following year Phillips sold a series of six pen and ink drawings to an anonymous buyer for £23,700 ($38,000). The set was published in 1926 under the title, ‘In which Piglet is entirely surrounded by water’. One of the most interesting Shepards was sold by Sotheby’s on November 16, 2000. The picture was the only known oil painting of Winnie the Pooh and Shepard is thought to have done it for a tea shop in Bristol called ‘Pooh Corner’. The estimated price was a hefty £20,000 – £30,000 ($32,000 – $48,000) but the unique painting surprised everyone when it actually sold for a staggering, £124,250 ($198,800)!