Roy Greenaway was born in Toronto and worked at the Daily Star in 1918 assisting an artist. He was a Star reporter at Queen’s Park for 48 years. On his off time he painted the streets of Toronto which he became well known for. He exhibited with the Royal Canadian Academy, the Montreal Society of Artists, the Northern Shore Arts Association of Gloucester and Massachusetts. Some of his works are in the Government of Ontario's collection as well as the City of Toronto Art Collection.