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 (Disney character) Pooh" (1977). Hal Smith (1980–1987) took over for the 1981 short "Winnie the Pooh Discovers the Seasons", and would maintain the role until Jim Cummings (1988–present) began voicing Pooh in the animated series "The New Adventures of Winnie the Pooh" (1988–1991). Cummings continues to voice Pooh (as well as Tigger) to this day. In 1961, Walt Disney Productions licensed certain film and other rights to the characters, stories and trademarks from Stephen Slesinger, Inc. and the estate of A. A. Milne. and made a series of cartoon films about him. The early cartoons were based on several of the original