Sterling said that the role of Winnie the Pooh was his favorite role that he did for Disney. In addition to his work as a voice actor with his distinctive high-pitched voice, Holloway was also a movie and stage actor and appeared in movies such as Meet John Doe (1941) and It's A Mad, Mad, Mad, Mad World (1963). He also appeared in a few Gene Autry movies and he also appeared on television in The Andy Griffith Show, A Family Affair, and Gilligan's Island.
Holloway was awarded the Disney Legend of 1991. He was escorted by the character of Pooh himself to receive the award. Sterling Holloway died on November 22, 1992 at the age of 87 from cardiac arrest. He was never married but did adopt a son named Richard Holloway who survived him. Following Sterling's death, Jim Cummings took over many of his characters for Disney.