Harris had a privileged upbringing in the wealthy Massey-Harris family in Ontario. From 1904 to 1907, he studied in Berlin, Germany with Franz Skarbina, Fritz von Willie and Adolf Schlabitz. On his return to Canada, he became a charter member of the Arts and Letters Club in Toronto, where he met most of the future members of the Group of Seven. Harris, along with the patron Dr. James MacCallum, financed the building of the Studio Building in Toronto, which opened in 1914, and kept his studio there, along with other Group of Seven members.
From 1910 to 1918, Harris painted the urban landscape of Toronto. In 1913, an exhibition of modern Scandinavian painting at the Albright Gallery in Buffalo had a profound effect upon Harris, due to its bold expression of raw northern landscape. After this, began to paint beautiful snow scenes as well as the urban scenes.
Another shift took place around 1918 when Harris traveled to Algoma on a sketching trip with fellow Group of Seven artists using a railway box car as a base. His work became more rugged and dramatic, and was shown in 1920 in the first Group of Seven exhibition, which established the presence of a new landscape school.
A pivotal experience occurred in 1921, when Harris went to the shore of Lake Superior, producing stark and compelling paintings of this region. His style of reducing the landscape to its essential form, and his interest in the spiritual in nature grew, and 1924 saw his first visit to the Rockies, and the start of his powerful mountain paintings. He also traveled to the Arctic, and was inspired by the sculptural landscapes there.
In 1934 Harris married his second wife Bess Housser, and relocated to Hanover, New Hampshire. He then moved to Sante Fe, New Mexico in 1938, where he became one of the founding members of the Transcendental Painting Group. Harris’s expansive beliefs based on Theosophy led him to explore abstraction deriving from the spiritual energy emanating from nature. Harris might have stayed in Sante Fe if it were not for the intervention of World War II. Canada, having declared war on Germany, set restrictions on funds leaving the country and, unable to get the money they needed to live on, the Harrises returned to Canada in 1940 and later that year settled in Vancouver. Harris continued with his abstract work, while becoming deeply involved in the Vancouver art scene. He served as an executor of Emily Carr’s estate and established the Emily Carr Scholarships, was the chair of the exhibitions committee at the Vancouver Art Gallery, and in 1944 became the President of the Federation of Canadian Arts. In 1960 he was appointed to the board of the National Gallery of Canada.
Harris’s life was a transformative one, beginning as a powerful nationalistic landscape painter, then evolving into abstraction which transcended borders.
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