Born in Cedartown, Georgia, Holloway was named after his father, Sterling Price Holloway, who himself was named after a prominent Confederate general, Sterling “Pap” Price. His mother was Rebecca DeHaven (some sources say her last name was Boothby). He had a younger brother named Boothby. The family owned a grocery store in Cedartown, where his father served as mayor in 1912. After graduating from Georgia Military Academy in 1920 at the age of fifteen, he left Georgia for New York City, where he attended the American Academy of Dramatic Arts. While there, he befriended actor Spencer Tracy, whom he considered one of his favorite working colleagues.  In his late teens, Holloway toured with stock company of The Shepherd of the Hills, performing in one-nighters across much of the American West before returning to New York where he accepted small walk-on parts from the Theatre Guild, and appeared in the Rodgers and Hart review The Garrick Gaieties in the mid-1920s. A talented singer, he introduced “Manhattan” in 1925, and the following year sang “Mountain Greenery”.  He moved to Hollywood in 1926 to begin a film career that lasted almost 50 years. His bushy red hair and high pitched voice meant that he almost always appeared in comedies. His first film was The Battling Kangaroo (1926), a silent picture. Over the following decades, Holloway would appear with Fred MacMurray, Barbara Stanwyck, Lon Chaney Jr, Clark Gable, Joan Crawford, Bing Crosby, and John Carradine. In 1942, during World War II, Holloway enlisted in the United States Army at the age of 37 and was assigned to the Special Services. He helped develop a show called “Hey Rookie”, which ran for nine months and raised $350,000 for the Army Relief Fund. In 1945, Holloway played the role of a medic assigned to an infantry platoon in the critically acclaimed film A Walk in the Sun. During 1946 and 1947, he played the comic sidekick in five Gene Autry Westerns.  Holloway’s voice work in animated films began in 1941, when he was heard in Dumbo (1941), as the voice of Mr. Stork. Walt Disney considered him for the voice of Sleepy in Snow White and the Seven Dwarfs (1937), but chose Pinto Colvig instead. Holloway was the voice of the adult Flower in Bambi (1942), the narrator of the Antarctic penguin sequence in The Three Caballeros (1944) and the narrator in the Peter and the Wolf sequence of Make Mine Music (1946).  He was the voice of the The Cheshire Cat in Alice in Wonderland (1951), the narrator in Susie the Little Blue Coupe (1952), Kaa in The Jungle Book (1967), and Roquefort in The Aristocats (1970). He is perhaps best remembered as the voice of Winnie the Pooh in Disney’s Winnie-the-Pooh featurettes. He was honored as a ‘Disney Legend’ in 1991, the first one to ever receive the award in the Voice category. His final role was the Hobe Carpenter, a friendly moonshiner who helps Harley Thomas (David Carradine) in Thunder and Lightning (1977).

Holloway acted on many radio programs, including The Railroad Hour, The United States Steel Hour, Suspense and Lux Radio Theater. In the late 1940s, he could be heard in various roles on NBC’s “Fibber McGee and Molly”. His distinctive tenor voice retained a touch of its Southern drawl and was very recognizable. Holloway was chosen to narrate many children’s records, including Uncle Remus Stories (Decca), Mother Goose Nursery Rhymes (Disneyland Records), Walt Disney Presents Rudyard Kipling’s Just so Stories (Disneyland Records) and Peter and the Wolf (RCA Victor).  Holloway easily made the transition from radio to television. He appeared on the Adventures of Superman as “Uncle Oscar”, an eccentric inventor, and played a recurring role on The Life of Riley. He was a guest star on Fred Waring’s CBS television program in the 1950s and appeared on Circus Boy as a hot air balloonist, Five Fingers (“The Temple of the Swinging Doll”), The Untouchables, The Real McCoys (in the 1960 episode “The Jinx”), Hazel, Pete and Gladys, The Twilight Zone (episode “What’s in the Box”), The Brothers Brannagan, Gilligan’s Island, The Andy Griffith Show, The Donald O’Connor Show, Peter Gunn as ‘Felony’, F Troop, and Moonlighting. During the 1970s, Holloway did commercial voice-overs for Purina Puppy Chow dog food and sang their familiar jingle, “Puppy Chow/For a full year/Till he’s full-grown!”. He also provided the voice for Woodsy Owl in several 1970s and 1980s United States Forest Service commercials. In 1982 he auditioned for the well known comic book character Garfield but lost to Lorenzo Music. In 1984, he provided voiceover work for a commercial for Libby’s baked beans.

Never married, Holloway claimed this was because he felt lacking in nothing and did not wish to disturb his pattern of life, but he had an adopted son, Richard.  Holloway died on November 22, 1992 of a cardiac arrest in a Los Angeles hospital. His body was cremated and his ashes scattered in the Pacific Ocean.  Voice actor 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. The show Animaniacs paid tribute to him by having Cummings (in his Pooh voice) narrate episodes like “Nighty Night Toon” and “The Warners and the Beanstalk”.