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 now-familiar red shirt and featured on an RCA Victor picture record. Parker Brothers introduced "A. A. Milne's Winnie-the-Pooh Game" in 1933, again with Pooh in his red shirt. In the 1940s, Agnes Brush created the first plush dolls with Pooh in his red shirt. Shepard had drawn Pooh with a shirt as early as the first Winnie-The-Pooh book, which was subsequently coloured red in later coloured editions. After Slesinger's death in 1953, his wife, Shirley Slesinger Lasswell, continued developing the character herself. In 1961, she licensed rights to Walt Disney Productions in exchange for royalties in the first of two