- Most well known as the illustrator of A.A. Milne's "Winnie the Pooh" books.
- Father of Graham Shepard who was killed in World War II and Mary Shepard who illustrated the Mary Poppins book series.
- Shepard in his childhood was a cheerful boy, fond of practical jokes and, in the current slang of the day, was described as a "giddy kipper." Kipper was a nickname which clung to him all his life.
- A.A. Milne initially thought Shepard's style was not what he wanted for Winnie-the-Pooh, but later on changed his mind. Milne also arranged for Shepard to receive a share of his royalties, understanding Shepard's contribution to Pooh's success.
- Shepard modelled Pooh on Growler, a stuffed bear owned by his own son. Growler no longer exists, having been given to his granddaughter Minnie Hunt and subsequently destroyed by a neighbour's dog.
- When World War I broke out in 1914, Shepard received a commission as a second lieutenant in the Royal Garrison Artillery, an arm of the Royal Artillery. On 16 February 1917, he was made an acting captain whilst second-in-command of a siege battery. He was awarded the Military Cross for his service at the Battle of Passchendaele. By the end of the war, he had achieved the rank of major.
- Late in life, Shepard came to resent "that silly old bear" as he felt that the Pooh illustrations had overshadowed his other works.
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