Portrait of the artist's son, Jonathan Richardson Jun. (1694-1771), aged 40

Richardson Senior was one of the most successful portrait painters of his generation, before semi-retiring in 1728. After that date he regularly drew himself and his eldest son, as well as other friends. The drawings of himself and his son have an extraordinary intimacy, in part due to the regularity with which he made them - often at least one drawing each week. Here, Richardson Junior is depicted wearing the soft cap usually worn within the house by gentlemen who would wear an elaborate wig in public. Father and son were very close, with Richardson Junior never marrying and continuing to live with his father throughout his life. They shared artistic and literary interests, and collaborated on two books.

While his drawings of friends are usually in graphite on vellum, or in pen and ink, the self-portraits and drawings of Richardson Junior are more often in a trois crayons technique of black, red, and white chalk, on blue or oatmeal paper. Susan Owens has suggested the choice of medium was probably dictated by location, with the messier chalk used only at home (S. Owens, Jonathan Richardson by Himself, London, 2015, p. 11).