Wilkie made his stage debut in 1899 and almost immediately began touring with three of the great Shakespeare companies, those of Rawson Buckley, Ben Greet and Frank Benson. After his experience with these companies and the numerous parts he played in Shakespeare he formed his own company and toured England, India, and Australia. In 1920 after his company’s successful runs in Melbourne and Sydney, he took his troupe over much of Asia. In all, he staged twenty-seven of Shakespeare’s plays. In 1932, he returned to England and again toured the provinces with Hamlet, The Merchant of Venice, The Taming of the Shrew, and Twelfth Night. He produced a few contemporary dramas, but most of his career was dedicated to Shakespeare and he kept his company together long after the demise of most other actor-manager groups.