The playwright Richard Cumberland (1732-1811) was Romney's most important early supporter in London, commissioning a series of portraits of himself and members of his family between 1768 and 1773, when the artist went to Italy. The present picture was once thought to represent Mrs Cumberland and one of her children, but the portrait of Mrs Cumberland with her Son Charles (circa 1770, Tate Britain) shows a woman with very different facial features.
This portrait is in fact more likely to be a fancy picture rather than a portrait, given that the features are partly hidden. It also does not appear to be a mother and child, but rather an older sister (or possibly a cousin or other family member) with a young child; perhaps in the act of teaching the child to read. The girl, in her mob cap, calls to mind Romney's Serena Reading canvases (see A. Kidson, George Romney 1734-1802, ex. cat., 2002, no. 97, pp. 165-67). Serena is the heroine of William Hayley's poem The Triumphs of Temper, published in 1780. Romney depicts her reading Fanny Burney's Evelina in the early hours of the morning. Serena wears a simple white gown and white mob cap, like the girl in the present picture. In the Serena canvases, the dress is obviously nightwear; in the present picture it seems to be the same, underlining the intimacy of the scene. The models may be members of Romney's family, or very close friends. Romney's contemporaries Reynolds, Gainsborough and Nathaniel Hone used family members and friends for fancy pictures, Reynolds's great-niece Theophilia Gwatkin posing as Simplicity, for example, and Gainsborough's daughters as Gleaners. David Mannings has described portraits of this kind as 'half-portrait, half-genre' (in N. Penny, Reynolds, ex. cat., 1986, p. 169).
A similarity has been noted between the boy in the present picture and the infant 6th Duke of Devonshire as depicted by Romney in 1790-91 (sold Sotheby's, London, 5 June 2008, lot 58). Romney presumably made his small oil sketch of the future Duke on one of the several occasions on which the child's mother, the famous Georgiana, Duchess of Devonshire, sat to him (see Ward and Roberts, op. cit., p. 45 and p. 128). The similarity seems to be a result of Romney's way of seeing and characterising young children: there are no later portraits of the 6th Duke or his sisters by the artist.
In their catalogue of Romney's works Ward and Roberts remark of this picture, 'This lovely sketch was purchased privately by Mr. Davis from the Long Collection' (ibid., II, p. 38). William Long (1747-1818), a surgeon and amateur artist, was a member of the 'Unincreaseables', a club whose membership (originally said to be limited to eight) included literary and professional men including Romney and the actor John Henderson. Richard Cumberland is also known to have attended as a visitor (see D. Cross, A Striking Likeness: the Life of George Romney, 2000, pp. 99, 130, 132). The Unincreaseables met at the Queen's Head, Holborn, at the Shakespeare, Covent Garden, or at members' houses. Long enjoyed a successful professional career. In 1791 he was elected senior surgeon at St. Bartholomew's Hospital, and he also became second master of the Royal College of Surgeons (ibid., p. 130). He had a small but notable collection of works by Romney, including the now lost John Henderson as Macbeth which he won in a raffle held by the Unincreaseables (Kidson, op. cit., p. 217, note 5). In his will, Romney left a gold ring to Long (Cross, op. cit., p. 205).