Wyndham's family intended him for a medical career, and he studied medicine while enthusiastically engaging in amateur theatricals in his spare time.
"Criterion farce" became a familiar feature of the West End theatre, usually risqué French pieces toned down to avoid shocking the Victorian British audience.
[3] In February 1862 Wyndham, who had by then adopted his stage surname,[n 1] made his professional debut at the Royalty Theatre as the juvenile lead opposite the young, but already experienced, Ellen Terry.
In the farce Grandfather Whitehead he won praise from the theatrical newspaper The Era, which found him "a very promising Light Comedian" and his playing "as easy, natural and perfect as it need be".
[3] He resumed his British stage career in a leading role in a play he had written, My Lady's Guardian, which opened at the Theatre Royal, Manchester in July.
[17] Of his later roles during the season, the most prominent was as the smuggler, Hatchett, in F. C. Burnand's new and immensely popular burlesque on Douglas Jerrold's nautical comedy, Black-Eyed Susan, with Oliver and Nelly Bromley.
In September and October of the same year he appeared at the Prince's Theatre, Manchester, in Kate Terry's farewell season, in which his roles included Mercutio in Romeo and Juliet, Claudio in Much Ado About Nothing, the clown Modus in James Sheridan Knowles's The Hunchback, and Laertes in Hamlet.
[19] Before returning to the West End, he went to his home town, Liverpool, to create the role of Roberto in W. S. Gilbert's extravaganza La Vivandière.
[20] Returning to London, Wyndham was then engaged for the Queen's Theatre, Long Acre, and there in October and November 1867 – as the gallant Dujardin in The Double Marriage and the seducer Hawksley in Still Waters Run Deep – he once again partnered Ellen Terry.
[9] After several more New York productions, and having established a reputation as a light comedian, he started an American touring company of his own, opening with The Lancers[n 3] in Washington DC in March 1871.
[n 4] Wyndham returned to England in 1873 and appeared for various managements including the Bancrofts, in new plays and revivals of classics (as Jack Rover in Wild Oats and Charles Surface again).
In September 1874 Wyndham inaugurated a series of matinées at the Crystal Palace in which, over three years, he presented nearly a hundred plays, and acted in many of them, in roles including Bassanio in The Merchant of Venice, and Mephistopheles in Faust and Marguerite; he staged but did not appear in Sophocles' Antigone and Oedipus at Colonus.
[3] Some Palais-Royal material required judicious modification for a respectable English audience of the 1870s, but The Times said, "His grace and vivacity were enchanting, and his lightness of touch relieved liveliness of offence".
[28][n 8] A rare failure was Gilbert's farce Foggerty's Fairy (1881), in which Wyndham appeared with his former employer, Mrs John Wood; it opened on 15 December and closed on 6 January.
[3] On his return to London he successfully continued with modern-dress farce for some years, before turning to period pieces, first in a revival of Wild Oats in May 1886, and later in the same year in T. W. Robertson's David Garrick, a piece with which he became closely associated, playing the title role hundreds of times, including a production in German (in his own translation) which he toured in Europe in 1888, appearing in St Petersburg before Tsar Alexander III and his court.
[12][19] David Garrick remained Wyndham's principal period-costume role, but he presented several more over the next decade, including Dion Boucicault's London Assurance (as Dazzle, 1890), and 18th-century comedies by Goldsmith, Sheridan, and O'Keeffe.
Read suggests that lack of early experience in provincial repertory had left Wyndham technically struggling with a part so different from his usual roles, but the reviews were friendly,[36] and it was the play that did not attract audiences.