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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…
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