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 a Day for Eeyore Robin, Pooh and finally Piglet all decide that "Tigger's all right, really". Only Hal Smith, Ralph Wright, John Fiedler, and Paul Winchell returned in the roles they had originated in. Kim Christianson became the fourth different actor to portray Christopher Robin in as many featurettes, after Bruce Reitherman, Jon Walmsley, and Timothy Turner. Dick Billingsley assumed the role of Roo after Dori Whitaker and Clint Howard portrayed him in the previous featurettes. Hal Smith and Laurie Main first took the roles of Winnie the Pooh and The Narrator in the 1981 educational film "Winnie the Pooh Discovers the Seasons", as