Henry Greswold Lewis was one of Constable's earliest and more eccentric patrons, and remained a good friend of the artist for over twenty years. They first met in 1807, when Constable was copying portraits for Lewis' brother-in-law, Wilbraham, 6th Earl of Dysart. Lewis commissioned this portrait shortly afterwards, although it was not completed until 1809. He was clearly pleased with the likeness, since several further versions were painted for members of his family, including his brother-in-law Orlando, 1st Earl of Bradford (in c. 1809-11); his cousin Jane Harries, for Knowle Hall, Warwickshire (in 1813); and his former ward, Mrs Mary Wilson-Ffrance, née Freer (in 1824) (Reynolds, op. cit, nos. 09.25, 13.28 and 27.46 respectively). Constable also painted several views of Malvern Hall, one of which, painted in 1809, now hangs in the Tate Gallery, London.
Lewis' more eccentric commissions to Constable include: a study of his ward, Mary Freer's eye 'for a shirt pint to which I will add the Hair' in 1809; a nine foot portrait of Lewis' Norman ancestor Humphri de Grousewolde, for the stairwell at Malvern Hall in 1818; and in 1829, a pen and ink drawing of a mermaid for an sign for the Old Mermaid & Greswolde Armes Inn, Solihull, which Lewis owned. That Constable was prepared to carry out such commissions is testimony to a strong and enduring friendship.