Gershon Iskowitz wanted to be an artist from an early age. His 1929-31 school records, held in the Kielce State Archives, indicates that he studied drawing and received good marks. After the outbreak of WWII, the Nazis established the Kielce Ghetto in 1941. When the Ghetto was liquidated in August 1942, Gerhson was first sent to the Henryków labour camp and later to labour camps at Auschwitz and Buchenwald. His parents and two siblings died in the Treblinka extermination camp; brother Yosl disappeared in Auschwitz. In his oral account years later, Gershon recalled that he was shot in the leg while attempting to escape. Remarkably, throughout these horrific experiences Iskowitz continued to create art, and in cleaning up after bombing raids he found not only food, but scraps of paper in the rubble. At night with stubs of pencils he chronicled the brutality of the camps, stating later that he felt that drawing was necessary to his survival. When Buchenwald was liberated in April 1945 he spent time in hospital recuperating before being admitted to the Feldafing Displaced Persons camp near Munich in October. There he began drawing his first camp memory works and paintings that included scenes of Feldafing.

In 1948 Iskowitz immigrated to Canada and settled in Toronto. He continued his memory works of pre-War Poland, the brutal Kielce Ghetto and camp experiences until 1955; some were reproduced in a 1966 Saturday Night article by Kildare Dobbs titled From the Ranks of Death. But beginning in 1952, he began taking annual trips to painter Bert Weir’s McKellar Lodge Summer Studio near Parry Sound, where he began his landscapes. By the end of the 1950s, these became atmospheric works that led to his mature period abstracts by 1965. Iskowitz's work was shown in solo and group public gallery exhibitions across Canada. His first solo exhibition was at the Hayter Gallery, Toronto in 1957, and beginning in 1964 he was represented by Gallery Moos in Toronto. In 1967 he received a Canada Council grant, which he used to travel to Churchill, Manitoba and took a flight over the sub-Arctic landscape and the coast of Hudson’s Bay. The views of the land from above delighted him - there were hundreds of little lakes all glittering in the sun, but equally in looking up to observe ever-changing cloud formations, which he would depict in watercolour and oil as brilliant topographical dances of light and colour. This northern landscape would inspire his art for the rest of his life, and thus his vividly coloured works, which he stressed were not abstract, but paintings of what he saw, are the works he is widely known for. Together with Walter Redinger, he represented Canada at the Venice Biennale in 1972. The Art Gallery of Ontario organized a retrospective in 1982 that toured to four other public galleries across Canada and to Canada House Gallery in London, England. In 1985, three years before his death Iskowitz decided to establish a foundation in his name and create a prize to support the work of a mature Canadian artist, acknowledging the importance of his own 1967 Canada Council grant and the opportunity that it had given him to formalize his mature style. The first prize was awarded in 1986. In 2007, the Gershon Iskowitz Foundation partnered with the Art Gallery of Ontario to continue to award this prize. Recipients have included Michael Snow, Paterson Ewen and Jack Shadbolt.