Why ‘The Andy Griffith Show’ and ‘Gilligan’s Island’ Actor Sterling Holloway Became an Iconic Voice Actor

by Matthew Memrick

A studio exec’s harsh words for actor Sterling Holloway, who appeared in “The Andy Griffith Show” and “Gilligan’s Island,” did not deter him.

The harsh criticism of having a “repulsive face” did not deter Holloway. The man who was the voice for Winnie the Pooh appeared in over 100 movies and 40 television shows.

According to MeTV, Holloway recounted the story to The Los Angeles Times in 1979. He showed up at Paramount Studios and stepped in front of a camera to be battered by the executive. 

But this was nothing new for the Georgia native. He often thought about quitting, but this moment had him in the pits. Three days later, Walt Disney found him and made the man a star.

The story is similar to actress Winona Ryder. According to IMDb, a casting director told Ryder that “she should not be an actress because she was not pretty enough.” She said Ryder “didn’t have it.” Ryder went on to have a successful acting career.

Holloway Started On The Farm

Long before he voiced Winnie The Pool’s catchphrase, “Oh, bother,” Sterling Holloway put on plays in his dad’s barn and got neighborhood kiddos involved. He aspired to the theatrical arts and enrolled with the American Academy of Dramatic Arts in New York at 15.

Later, the 5-foot-9 man enlisted in the Army on July 19, 1942. The Army assigned him to Special Services, where he helped develop a military-themed show called “Hey Rookie.” The show ran for nine months in Los Angeles and earned $350,000 for the Army Relief Fund.

Sterling Holloway took small comedic parts in shows. But like the executive said, his looks kept him from the dramatic roles he wanted. Holloway wanted those serious roles.

One day, a chance meeting with Frank Capra helped Holloway’s dream. Holloway visited a cousin who connected to Capra’s assistant director. Capra spied upon the actor and put a bank teller role in his 1932 “American Madness” film.

After that, many directors sought Holloway for their films, but his work with children’s entertainment entrepreneur Disney led to a long career.

Holloway Had a Long Career

Before he died in 1992, Sterling Holloway had roles on “The Andy Griffith Show” and “Gilligan’s Island.”

And lots of voice acting work. He had roles in “Dumbo,” “Bambi,” “Alice in Wonderland,” “The Jungle Book,” “The Aristocats,” and, of course, “Winnie the Pooh.”

He earned enough money to design a hilltop house with an ocean view. The place held his extensive art collection, and it became known as a “lived-in museum.”

Holloway owned work from Andy Warhol and Roy Lichtenstein, but one notable work by Karel Appel stood out. Appel did a portrait of Holloway sitting on his couch with his distinctive face.