Biographer Rod Taylor told Joe Sibilia with "Nostalgia Tonight" about how Holloway continued to honor his connection to Disney and the characters he voiced in his decades with the company.
The original voice of Winnie the Pooh was ultimately pushed out of his role.
Sterling Holloway was the first voice actor to lend his talents to Winnie the Pooh, in addition to roughly a dozen other Disney characters. His biographer, Rod Taylor, chatted with Joe Sibilia on Nostalgia Tonight about Holloway's relationship with Disney.
Holloway first worked with Disney on 1941's Dumbo, voicing Mr. Stork. It was the beginning of a decades-long partnership that also saw him as Alice in Wonderland's Cheshire cat. Taylor explains that Disney discovered Holloway years prior, however.
"I'm convinced that Walt was one of the thousands of people who attended the Midsummer Night's Dream production at the Hollywood Bowl that Sterling was in, and I think that's what put him into Walt's mind. The animators told me they knew him from radio," Taylor shared.
Once he came into that world, Taylor says Holloway was "impressed with Disney, not because of its reputation, not because of the talent, not because of Walt, the person. He was really impressed with the physical plant. He was impressed with how Walt had invested in the studio, in the recording technology, and then in the animation technology, which, of course, by today's standards, was pretty rudimentary."
Sibilia also spoke with Bruce Reitherman, the voice of Christopher Robin as well as the Honey Tree and Mowgli in The Jungle Book.
"I absolutely think that Sterling's performance in Winnie the Pooh was the mortar between all the other building blocks, that without that, the thing would not have held up. It would have felt saccharine or something else, but Sterling managed to bring that depth of character to it that I think was just fundamental to the film's success," he shared.
Holloway had the support of Walt Disney, though the two weren't close. It was through that understanding that Holloway was cast as Winnie the Pooh, despite some others' comments that his voice was already "overused" by the studio.
Reitherman shared, "It's really Walt's decision, and if Walt wants to use Sterling Holloway again, then I suspect that Wooly, my dad, says, 'Well, that's what we're gonna do. We're gonna make the very best of that.'"
"So if there's any grousing at all, and I doubt there was much because Sterling is such an obvious choice and such a perfect choice, I think it was very quickly abated by the sheer enthusiasm you would have had as you listened to the recordings."
Holloway enjoyed great success and admiration for his portrayal of Winnie the Pooh. In 1977, when he suffered a heart attack, then-President Jimmy Carter called to check in on him at the urging of his daughter. Not working during his recovery was "devastating" for the voice actor, who was in his early 70s at the time.
When Holloway and his agent realized what was happening, Taylor says, "his agent was PO'd."
"Sterling created that role, but we all forget entertainment is a business, and if you're producing a TV show, you know, 13 or 26 episodes, especially animation, you gotta be able to knock out the voiceovers," he explained.
"And so the one time that I know Disney asked Sterling to do a test read for a Pooh Project after he had been Pooh for more than 10 years, was The New Adventures of Winnie the Pooh, which was an animated series. And at that age, you know, he's close to 80, he just couldn't knock them out," Taylor admitted.
"Now, he would still sound like Pooh, and he still, you know, had the ability to inflect and to do all those little things, but he just couldn't crank them out, and that's when they pivoted to Jim Cummings. There's no way that Sterling would have been physically up for that."
Holloway enjoyed a spirited final few years of life, spending time with his beloved nurse and a few friends in his area in Georgia. He died in 1992 at the age of 87.