Born in Devon, Rupert won an art scholarship to Blundell's School, Tiverton, before going on to study Fine Art and Art History at the University of Wales, Aberystwyth.  He exhibits regularly in various shows at the Mall Galleries, London including the Threadneedle, Discerning Eye, Lynn Painter Stainers Exhibition, and in 2014 he won second prize in Artist and Illustrators' Artist of the Year award. Rupert has won both the David Messum Prize and the Marine House Gallery Award for paintings shown with SWAc before becoming an Academician in 2013.