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 (book) 1960s, the Milne story lines were used by Disney in its cartoon featurette "Winnie the Pooh and the Honey Tree". The "look" of Pooh was adapted by Disney from Stephen Slesinger's distinctive American Pooh with his famous red shirt that had been created and used in commerce by Slesinger since the 1930s. "Winnie-the-Pooh" was shortly followed by "The House at Pooh Corner", also by Milne. "Return to the Hundred Acre Wood", by David Benedictus was the first official post-Milne Pooh book written with the full backing of A. A. Milne's estate, which took the trustees ten years to agree to.