[7][a] He joined the corps dramatique of Sydney's Victoria Theatre in 1869; his first billing was with Marie Duret in Lucretia Borgia for Rosa Cooper.

[1] Holloway leased the Theatre Royal (Hobart) and assembled a "Star Dramatic Company" in 1878–9 to support William Creswick and Helen Ashton, playing Sheridan Knowles' Virginius and The Hunchback and several Shakespeare classics.

[13] They took a holiday in London 1884–5, during which time Essie Jenyns immersed herself in the work of Sarah Bernhardt, Ellen Terry, Mary Anderson and other great English (and American) actresses.

They returned to Australia with a hectic touring schedule, playing Frank Harvey's A Mad Marriage at the Academy of Music, Ballarat in January 1886,[14] and in February the same author's The Ring of Iron at the newly opened Academy of Music in Launceston, to excellent reviews: play, cast (notably Essie Jenyns, in her first professional appearance in Tasmania), and the theatre itself.

[15] When they returned to the Opera House, Sydney however, The Ring of Iron was described by one reviewer as a "tawdry melodrama" which was "soon withdrawn"[16] in favor of Mrs G. W. Lovell's Ingomar the Barbarian, with Holloway in the title role and his wife as Aetoea, a part she knew from her early days with the company.

Holloway and his wife left Melbourne for London by SS Mogul on 7 November 1888, ostensibly for a holiday,[18] leaving the company in the hands of his brother Charles (1848–1908) and never returned.

Ever the journeyman actor, Charles joined Bland Holt and secured a reputation as an intelligent interpreter of supporting roles.

[1] Made quite wealthy by the successes of the previous year, the Holloways settled in England in April 1889, and purchased a property, "Waratah", near London.

He was well received by press and public, and appeared in the part for several weeks with Ellen Terry and the Lyceum cast, then during Irving's convalescence the two artists alternated.

[20] They made three tours to South Africa with a company that included his wife, his son W. D. Holloway, and his two daughters Juliet and Theodora.