Ernest Shepard was born the son of a architect, in London on December 10, 1879. As a child, Ernest had two big hobbies - watching the soldiers practice, and drawing. He decided on a career as an artist and was 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, and earned two scholarships while there.
Shepard met Florence Chaplin at the Academy and married her in 1904. They had two children - Graham and Mary. Shepard always dreamed of working for Punch, since it was the premier showcase in Britain for sketch work. After trying unsuccessfully many times, in 1907 he finally had two drawings accepted by the magazine. Gradually, more and more work was accepted, but he still was not yet working for them on a regular basis.
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 would later introduce him to Aland Milne.
E.V. Lucas named Shepard when A.A. Milne asked him to recommend someone to illustrate some children's verses he would be publishing in Punch. At first Milne was not keen to use Shepard, but when his illustrations were a success Shepard went on to illustrate all of 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 in 1943 he married Norah Carrol. Shepard ceased to be a regular cartoonist at Punch in 1949, but continued to provide drawings monthly. He was sacked in 1953 by Malcom Muggeridge, the new editor. Throughout the rest of his career Shepard illustrated books for many leading authors of the period, including several for Kenneth Grahame. Shepard was in fact the fourth illustrator to draw the characters for 'Wind in the Willows,' but the only one who managed to capture the essence of the animals that Grahame had in mind. He remained busy as an illustrator his whole life and even managed to write two children's books of his own in his mid eighties. These were titled Ben and Brook (1966) and Betsy and Joe (1967). Though the books didn't gain much popularity, their publication gave Shepard great pleasure. Shepard also colored his original line drawings for 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.