Gainsborough painted portraits at all periods of his career and they provided the majority of his income. Some were initiated by the artist and in the 1780s, when he was expending much of his energy on so-called ‘Fancy’ pictures, the lengthy process of painting a couple of important portraits raises further questions about their classification, their intention and their purpose. This lecture examines this dichotomy and shows how very inventive Gainsborough’s work was during the last decade of his life.