Born in Tunbridge Wells, Benson was educated at Winchester and New College, Oxford, and at the university was distinguished both as an athlete (winning the Inter-university three miles) and as an amateur actor. In the latter respect he was notable for producing at Oxford the first performance of a Greek play, the "Agamemnon", in which many Oxford men who afterwards became famous in other fields took part. A year later, at the invitation of Herbert Branston Gray, he staged a Greek language production of "Alcestis" at Bradfield College, himself playing Apollo.