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 the Blustery Day Corner"), "In which Pooh & Piglet go hunting and nearly catch a Woozle" (Chapter III of "Winnie the Pooh"), "In which Piglet does a very grand thing" (Chapter VIII from "The House at Pooh Corner"), "In which Christopher Robin gives a Pooh Party and we say goodbye" (Chapter X of "Winnie-the-Pooh") and "In which Piglet is entirely surrounded by water" (Chapter IX of "Winnie-the-Pooh"), with elements taken from "In which Piglet meets a Heffalump" (Chapter V from "Winnie-the-Pooh": Winnie the Pooh's nightmare of Heffalumps and Woozles). In A. A. Milne's original story, Pooh shows more initiative during the flood, finding