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Cherrington completed more than 800 paintings. His subjects varied from farmers' prize stock animals, to portraits. He also painted many expressionism works and later went on to use his skills illustrating children's books. These varied from nature books to weekly illustrated comics.
Among his best works was a portrait of Rab Butler who was a former British Chancellor of the Exchequer. Cherrington's portrait of Butler was as a Master of Trinity College, Cambridge which was accepted into the Royal Society of Portrait Painters. A number of his other artworks were also shown in the RSOPP exhibitions between 1969 and 1974.