In response to growing German propaganda during the First World War, the British Government formed a special Propaganda Department, which used visual art as a means of boosting up the morale of civilians and British soldiers on the Front. The War Artists‟ Scheme brought into being under the auspices of the Propaganda Department in 1914 allowed some of the most promising British artists to produce memorable paintings. The works documented the numerous sites of the Western and Eastern Front. In addition, the artists employed under the scheme presented the nation with portraits of notable military and political figures engaged in the war effort. This thesis investigates how William Orpen, an established society portraitist and A.R.A., fits into the War Artists‟ Scheme. His position was problematic: as a painter working in an early twentieth-century descriptive vein and older than other artists at the Front, how did he fare in this troubled context? Orpen‟s work on the Western Front (France and Flanders) has been so far neglected and considered to be of little relevance in comparison to what other avant-garde artists produced during the same time span. The thesis investigates how Orpen, although painting in an early twentieth-century representational style considered slightly passé, embedded in his works innovative means of expression, creating vivid, haunting imagery, adding to a body of work which was supposed to be documentary a depth reminiscent of ecclesiastic artistic practice. The thesis attempts to re-evaluate Orpen‟s war oeuvre, an aspect of the artist‟s rich imagery hitherto left to oblivion.