Roland Gissing was born in 1895 in Willersey, Worcester, England, the son of author Algernon Gissing, and nephew of noted English novelist Robert George Gissing. He studied art for a few years at George Watson's College in Edinburgh in the early part of the century, however he was primarily self-taught. His imagination fired by images of the “wild west” that he saw in Edinburgh's moving picture theatres, he immigrated to Canada and in 1913 at the age of 18, arrived in Calgary. For the next decade, he worked as a cowboy on ranches in Alberta, Montana, Nebraska and Arizona. During this period, he met the cowboy artist Charlie Russell in Montana who provided encouragement, as did the Western writer Will James, who he met in Nevada. In 1923, he purchased a homestead west of Cochrane, Alberta, near the junction of the Ghost and Bow Rivers and it was there, before the inspiring visual beauty of the Alberta foothills, and with the encouragement of the Canadian painter C.W. Jefferys, that he began his career as a full-time artist. He was honing his artistic skills and becoming quite well-known, when in 1944 his home and studio full of paintings burned to the ground. He quickly re-established himself and after selling the property in 1955 purchased twenty acres of land for a new studio south of Calgary near Okotoks, where he lived and painted until his death in 1967.
Working primarily with pastels and watercolour in his early works, Gissing turned almost exclusively to oils in the 1930’s. With his frank and colourful depiction of the natural beauty of his Western subjects, his work became very popular. After the discovery of oil in Alberta, his paintings became vigorously collected by oil company executives and added to their corporate collections, and began showing up in other private and public collections as well. These include the Queen's collection, the Edmonton Museum of Art (later the Alberta Gallery of Art) collection and the Vancouver Art Gallery among many others.