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 Tigger Too Winnie the Pooh and Tigger Too Winnie the Pooh and Tigger Too is a 1974 animated featurette from Disney released as a double feature with "The Island at the Top of the World". It was nominated for an Academy Award for Best Animated Short Film, but lost to "Closed Mondays". It was later added as a segment to the 1977 film "The Many Adventures of Winnie the Pooh". A soundtrack album was released simultaneously and featured such songs as "The Honey Tree" and "Birthday, Birthday." The film, whose name is a play on the slogan "Tippecanoe and Tyler too" made