Holloway began his stage career in 1899 as a boy in the production of The Merchant of Venice.[3] In 1907, Holloway joined the Benson Company.[1] Holloway played the leading part in several Stratford-upon-Avon festivals and was leading man at The Old Vic in London from 1925 to 1928.[3] He retired from The Old Vic in 1949. He also performed at the Open Air Theatre. He acted for the Phoenix Society. He worked alongside Edith Evans and also worked as an actor-manager.[2] In America, he worked alongside Walter Hampden in Othello as Iago.[2]
Holloway married and his wife died in 1959. In 1965, Holloway refused to leave his home of 52 years in Marylebone and halted a construction project.[3] Holloway went by the nickname "Bay".[2]
Holloway died on 15 April 1967, at the age of 83, at his home in London.[3]
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