[5] He did voice acting for The Walt Disney Company, playing Mr. Stork in Dumbo, Adult Flower in Bambi, the Cheshire Cat in Alice in Wonderland, Kaa in The Jungle Book, Roquefort the Mouse in The Aristocats, and the title character in Winnie the Pooh, among many others.

[citation needed] In his late teens, Holloway toured with the stock company of The Shepherd of the Hills,[7] 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 revue The Garrick Gaieties in the mid-1920s.

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.

[8] Walt Disney originally considered Holloway for the voice of Sleepy in Snow White and the Seven Dwarfs (1937), but chose Pinto Colvig instead.

His final role was Hobe Carpenter, a friendly moonshiner who helps Harley Thomas (David Carradine) in Thunder and Lightning (1977).

He guest-starred on Fred Waring's CBS television program in the 1950s and appeared on Circus Boy as a hot air balloonist.

Some other series on which he performed include Five Fingers (episode "The Temple of the Swinging Doll"), The Untouchables, The Real McCoys ("The Jinx"), Hazel, Pete and Gladys, The Twilight Zone ("What's in the Box"), The Brothers Brannagan, Gilligan's Island, The Andy Griffith Show, The Donald O'Connor Show, Peter Gunn, F Troop, and Moonlighting.

[14] Holloway was an avid art collector, important in the early careers of many local Los Angeles area artists such as Edward Kienholz and Billy Al Bengston.

The design of the house included unique elements such as large built-in flat file drawers to hold prints and other unmounted works from his collection as well as features specifically designated for certain notable artworks, such as the commissioned revolving wooden sunshade panels made by Robert Cremean which faced the setting sun, and sculptured front doors by John Mason.