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In 1978, Whitehead moved to London, Ontario to take up an academic post at Western University. With the encouragement of some new friends there, he began to play and compose jazz for the first time, and formed the Oliver Whitehead Quintet (1983–1990), fronted by sax player Chris Robinson, to play original compositions by him and pianist Patrick Dubois. Their first LP was nominated for Best Jazz Album in Canada's Juno Award of 1985. The quintet played twice at the Montreal International Jazz Festival, as well as other jazz fests in Detroit, Toronto, Ottawa, Edmonton and Vancouver.
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