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 (franchise) animated feature film. Inspired by A. A. Milne's stories of the same name, the film is part of Disney's "Winnie the Pooh" franchise, the fifth theatrical Winnie the Pooh film released, and Walt Disney Animation Studios' second adaptation of "Winnie-the-Pooh" stories. Upon learning that Eeyore has lost his tail, the residents of the Hundred Acre Wood start a contest to see who can find a new one for the melancholy donkey — with a pot of honey going to the winner. Amid the goings-on, Owl mistakenly relates the news that Christopher Robin has been abducted by a monster called The