Robinson is raised in a Protestant and Unionist family in which he is the youngest of seven children. His father, Andrew Robinson, is a middle-class stockbroker who in 1892 decides to become a clergyman in the Church of Ireland in the small Ballymoney parish, near Ballineen in West Cork. A sickly child, Robinson is educated by private tutor and at Bandon Grammar School. In August 1907, his interest in the theatre begins after he goes to see an Abbey production of plays by W.B. Yeats and Lady Gregory at the Cork Opera House. He publishes his first poem that same year. His first play, The Cross Roads, is performed in the Abbey in 1909 and he becomes manager of the theatre towards the end of that year. He resigns in 1914 as a result of a disastrous tour of the United States but returns in 1919. He is appointed to the board of the theatre in 1923 and continues to serve in that capacity until his death. His Abbey career and production involvement can be found in the Abbey archives.
As a playwright, Robinson shows himself as a nationalist with plays like Patriots (1912) and Dreamers (1915). On the other hand, he belongs to a part of Irish society which is not seen as fully Irish. This division between the majority native Irish (Roman Catholics) on one side and the Anglo-Irish (Protestants) on the other can be seen in a play such as The Big House (1926), which depicts the burning of a Protestant manor home by the Irish Republican Army (IRA). Robinson’s most popular play is The Whiteheaded Boy (1916).
Other plays include Crabbed Youth and Age (1924), The Far Off Hills (1928), Drama at Inish (1933), and Church Street (1935). Drama at Inish, which is presented in London and on Broadway as Is Life Worth Living?, is revived as part of the 2011 season at the Shaw Festival at Niagara-on-the-Lake, Ontario, Canada, with Mary Haney in the role of Lizzie Twohig. Robinson’s fiction includes Eight Short Stories (1919). In 1931 he publishes a biography of Bryan Cooper, who had recently died. In 1951, he publishes Ireland’s Abbey Theatre, the first full-length history of the company.
He publishes an edited edition of Lady Gregory’s diaries in 1947. In 1958 he co-edits with Donagh MacDonagh The Oxford Book of Irish Verse. He is also a director and producer, in 1930 producing a play by Irish playwright Teresa Deevy called The Reapers. In 1931 he is co-director of A Disciple along with W.B. Yeats and Walter Starkie.