In 1896, he married Dorothea Baird, who, after playing the part of Trilby the year before, was, at that time, the best known actress in Britain. HB & Dorothea had a son Laurence(1897-1988) who became a well known Hollywood art director and a daughter Elizabeth(b. 1904). HB continued to be part of his father's company, but soon felt the need to branch out. In 1898, he joined George Alexander at the St James's Theatre where he is played Don Juan in Much Ado About Nothing, and appeared in the surprising hit, The Ambassador, a play written by Pearl Mary Teresa Craigie.
For the following seven years, the couple, selecting the parts that appealed to them, moved between companies, sometimes together and sometimes separately. In 1900, they both appeared in Beerbohm Tree's production of A Midsummer Night's Dream that ran for 153 performances at Her Majesty's Theatre.
In 1904, only a year before his father's sudden death on October 13, 1905, Irving played Hamlet for the first time. The production, which was a popular success, was presented at the Adelphi Theatre, with Oscar Asche as Claudius, Walter Hampden as Laertes and Lily Brayton as Ophelia.
After his father's death, he established his own company, that included his wife, and toured most provincial cities, playing mainly repeats of Sir Henry Irving's best remembered performances. For the opening night of the new King's Theatre in Southsea he presented Charles I, The Bells and The Lyons Mail. Occasionally, other plays were presented including, most successfully, Dr Jekyll and Mr Hyde at the Queen's Theatre, London.
In 1911, Irving, Baird and their London Company toured Australia, again presenting Hamlet. Two years later, Baird retired from the stage, while Irving kept on performing. In 1913 he visited South Africa, and a photograph records his dinner with the Owl Club in Cape Town. In 1914, he appeared with Basil Rathbone in The Sin of David at the Savoy Theatre.
H.B.Irving was also a founding member of Our Society with Arthur Conan Doyle, Arthur Diosy, J.B. Atlay, and the Coroner Ingleby Oddie (among others). Our Society is the still flourishing "Murder" Club in London, where old crimes are discussed at regularly held dinners.