I am investigating the Royal Shakespeare Company’s vast collection of fine art and sculptures which have been acquired throughout the years since its founation as the Shakespeare Memorial Theatre’s Picture Gallery in 1881. The collection contains works of art painted by 17th century to contemporary masters, majority of which depicting scenes from Shakespeare’s works, actors, actresses, significant people in the institution, and of course Shakespeare himself. With particular focus on selected works’ provenance and material history, I aim to contextualise the collection and propose best practices and approaches towards its digitisation. In this contextualising the collection, I hope to unearth and re-“present” the collection in narratives that might reveal and/or disentangle Shakespeare from legacies of colonial and imperial past and frame the ways by which the Royal Shakespeare Company can move forward to understand its own collection and, given this, its role and responsibility to society and culture as a theatre-museum dedicated to the promotion of Shakespeare and British arts and humanities. The project is interdisciplinary in its nature: weaving together different disciplines from history, visual arts, literature, culture, and digital humanities.