The Many Adventures of Winnie the Pooh derived from three previously released animated featurettes Disney produced based upon the Winnie-the-Pooh books by A. A. Milne: "Winnie the Pooh and the Honey Tree" (1966), "Winnie the Pooh and the Blustery Day" (1968), and "Winnie the Pooh and Tigger Too" (1974). Extra material was used to link the three featurettes together to allow the stories to merge into each other. A fourth, shorter featurette was added to bring the film to a close, originally made during production of "Blustery Day" (based on the presence of Jon Walmsley as Christopher Robin). The sequence was based on the final chapter of
Winnie-the-Pooh: The Best Bear in All the World A. A. Milne in his own literary game. I also wanted to find a way of successfully introducing a brand new character into Pooh's world, whilst being sympathetic to the tone and style of the original books. The thought of Pooh encountering a penguin seemed no more outlandish than his meeting a kangaroo and a tiger in a Sussex wood, so I started thinking about what might have happened if, on a rather snowy day, Penguin had found his way to Pooh Corner." "The Stylist reports that Penguin is the first new character to be authorised by the Milne estate.