[n 1] Cherry made his first appearance on the stage at the Queen's Theatre, Manchester, 1897, as Mardian in Antony and Cleopatra with Louis Calvert, subsequently playing in Hamlet, and other Shakespeare plays at the same theatre.
His West End debut was in Sweet Nell of Old Drury at the Haymarket Theatre in August 1900, and played intermittently in Neilson and Fred Terry's company between then and 1912.
[3] In September 1912 he went to the United States, and appeared in Chicago, as John Rhead in Milestones, subsequently touring in the same part.
[3] After returning to London he appeared mainly in modern plays, but played Cinna in the Shakespeare Tercentenary production of Julius Caesar with F. R. Benson in the title role, Arthur Bourchier as Brutus, H. B. Irving as Cassius and Henry Ainley as Mark Antony.
[4] In May 1919 he succeeded Charles Hawtrey in the leading male role in Frederick J. Jackson's comedy The Naughty Wife, co-starring with Gladys Cooper,[3] and in August of that year, he, Hawtrey and Cooper played the three lead roles in W. Somerset Maugham's farce Home and Beauty at the Playhouse Theatre.