Well known for his voice acting for that willy nilly silly old bear, Winnie the Pooh, Sterling Holloway never had much trouble breaking into show business. A graduate of Georgia Military Academy and a student of the American Academy of Dramatic Arts in New York, Holloway had already starred in several Broadway shows by the time he was in his early twenties - and Hollywood was calling. Holloway was never considered a pretty man, and was even fired from at least one on-screen job because of his appearance. However, it wasn't his looks that made him famous, so once the silent era of movies had started to end, Holloway's voice was in great demand.
Walt Disney had his eye on this voice actor early on, and even suggested that he play a part in the 1937 animated classic Snow White and the Seven Dwarfs. It was not until Dumbo (1941) that Sterling got his start with Disney. Getting to both speak and sing, he played the small part of the Stork who delivered the baby Dumbo. This was followed by another small part as the voice of the adult Flower the Skunk in Bambi (1942), several narration parts, and other more involved characters such as the Cheshire Cat in Alice in Wonderland (1951).
Holloway brought Winnie the Pooh to life in Winnie the Pooh and the Honey Tree (1966), Winnie the Pooh and the Blustery Day (1968), and Winnie the Pooh and Tigger Too (1974). Around this same time, he was asked to play the part of Kaa the Snake in Disney's The Jungle Book. His character portrayal and ad-libbing of this villain actually helped shape the storyline and change the planned ending of the movie.
Sterling Holloway was honored in 1991 as a Disney Legend. He died on November 22, 1992 at the age of 87. Most people never knew what he looked like, but everyone knows what he sounded like.
A sample of his work:
After the death of Mr. Holloway, Hal Smith (the voice of Owl) took over the voice of Winnie the Pooh. Later movies and the new TV series used the voice of Jim Cummings for both Winnie and later Tigger as well.