Ernest Shepard was born in London on December 10, 1879. As a child he had two big hobbies - watching the soldiers practice, and drawing. He decided to pursue a career as an artist, encouraged by his father. After attending a special art school, Shepard entered the Royal Academy School in 1897 as one of it's youngest students, earning two scholarships.
Shepard met Florence Chaplin at the Academy and married her in 1904. They had two children - Graham and Mary. In the First World War Shepard enlisted in the Army, rose to the rank of Major and was awarded the Military Cross for bravery in the field. During these years, he sent jokes about the battles to Punch. Shortly after his return from the front, he was invited to join the Punch Editorial Table. He had finally realised his dream of working for Punch. Here he met E.V. Lucas, who later introduced him to A.A. Milne. E.V. Lucas recommended Shepard to A.A. Milne when Milne asked about an illustrator.
At first Milne was not keen to use Shepard. However, when his illustrations were a success, Shepard went on to illustrate all of the Winnie the Pooh books. Despite the success of the partnership, the two men only had a working relationship and never became close friends. Unfortunately, Florence died in 1927 and Shepard remained unmarried for several years until 1943 when he married Norah Carrol.
Shepard also colored his original line drawings for the new editions of 'Winnie the Pooh' (1973) and 'The House at Pooh Corner' (1974). 'The Pooh Story Book', released in 1976, contained new line and color pictures by Shepard. In his ninetieth year, Ernest Shepard donated 300 of his preliminary sketches for the Pooh drawings to the Victoria and Albert Museum, where they were exhibited in 1969. These drawings have since been exhibited in many galleries in Britain, as well as in Holland and Australia, and have now been published as 'The Pooh Sketch Book,' edited by Brian Sibley. Ernest Shepard died in 1976, in the fiftieth anniversary year of 'Winnie the Pooh'.