Rupert Shephard attended the Slade School of Art in the late 1920s. Following his time at Slade, Shephard worked as schoolmaster by day but spent many evenings painting. He primarily exhibited with the London Group and enjoyed a solo exhibition in 1939 bringing with it great recognition for his unique talent. Like several other arists Rupert worked as a war artist and draughtsman between 1940 to 1945. Following the war, Rupert moved to South Africa. There he became director of the well respected Michaelis Art School located at the University of Cape Town. Following the death of his first wife, Rupert returned to the UK. 10 years later he was elected to the Royal Society of Portrait Painters. Rupert continued to paint until his death in 1992.