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Stage
Holmes began his stage career in vaudeville and made his first professional appearance at Keith's Theatre in Boston in 1899. In 1900, Holmes appeared George Bernard Shaw's Candida in Chicago, the first production in the United States. Noted British theater critic William Archer saw the production and encouraged Holmes to go to London to further his career. Holmes sought out Archer in London some months later and joined the company founded by Olga Nethersole. He achieved only middling success before returning to the American stages.

He made his Broadway debut in February 1900 in the controversial play Sapho, which was briefly closed for indecency. Holmes played Rosencrantz with E. H. Sothern in a production of Hamlet and toured with Robert Edeson. He appeared in stage hits such as The Commuters, The Music Master, and His Majesty Bunker Bean.