After securing a place to study English Literature at Trinity College Oxford, Olly became actively involved in the university's dramatic society. Upon graduating he was awarded a scholarship to train at the London Academy of Music and Dramatic Art (LAMDA) and studied there for two years. Upon graduating from LAMDA, Ollly met Gregory Doran - the Artistic Director of the Royal Shakespeare Company (RSC) - and was offered the title role in Shakespeare's "lost play" Cardenio. Doran directed and Olly performed the role to critical acclaim, cited as a "dashing professional debut" for Olly by Mark Shenton writing for The Stage, noted for "a beguiling Cardenio" by Mark Taylor at the Independent and being telegraphed as a "talented young man on the path to future stardom" by Simon Tavener at London's leading theatre website WhatsOnStage. While at the RSC, Olly also worked with acclaimed British pl…
