Sterling Holloway Hal Smith took over the role of Winnie the Pooh for the 1981 short "Winnie the Pooh Discovers the Seasons". He would maintain the role until Jim Cummings replaced him in 1988 for "The New Adventures of Winnie the Pooh" and also took over most of Holloway's other voice roles, including Kaa in "Jungle Cubs" and "The Jungle Book 2". Sterling Holloway Sterling Price Holloway Jr. (January 4, 1905 – November 22, 1992) was an American character actor and voice actor who appeared in over 100 films and 40 television shows. He was also a voice actor for The Walt
Winnie the Pooh and the Honey Tree autobiography, "Walt's Time": The film's plot is based primarily on two A. A. Milne stories: "In which we are introduced to Winnie-the-Pooh and some bees, and the stories begin" (Chapter I of Winnie-the-Pooh), and "In which Pooh goes visiting and gets into a tight place" (Chapter II of Winnie-the-Pooh). Walt Disney first learned of the Winnie the Pooh books from his daughter, Diane. "Dad would hear me laughing alone in my room and come in to see what I was laughing at," Diane later recalled. "It was usually the gentle, whimsical humor of A. A. Milne's Pooh stories. I read