Although she had no formal training at either drama school or in repertory, Anna Massey made her first appearance on stage in May 1955 at the age of 17, at the Theatre Royal, Brighton, as Jane in "The Reluctant Debutante", subsequently making her first London appearance in the same play at the Cambridge Theatre in May 1955 "and was suddenly famous". She then left the cast in London to repeat her performance in New York in October 1956. In the 1990s she appeared with Alan Bennett in a dramatised reading of T.S. Eliot's and Virginia Woolf's letters, in a production at the Charleston Festival devised by Patrick Garland.