The narrative of Joseph Wright’s figures is eloquent and complex. In many ways, the sitters defined themselves and their cultural aspirations for posterity through clothing, posture and props. However, Wright subverts the tenets of eighteenth-century portraiture as he attempts to identify the physical markers that give the viewer a closer understanding of character. The painting of Thomas Day, for example, is far removed from the conventional portraiture of the wealthy gentleman. Its signifiers suggest the complexities of Day’s character. Most of what we know of the eccentric Day has come to us through Anna Seward’s unorthodox biography of Erasmus Darwin and his circle. This text is supplemented by letters between Seward and Walter Scott, which disclose the publishing censorship levelled at her memoir of Day when she attempted to find a psychological cause for his experiments with education and his rejection of wealth and luxury. Her private letters give an alternative view of the public figure that was part of her literary coterie, her “dear Quartetto.” This essay discusses the representation of character in Wright’s portrait of Thomas Day and decodes its cultural markers through a synthesis of painting and word-painting.