The subject of the present drawing was one that Romney returned to over a period of fifteen years. The subject is first seen as one of the Liverpool Cartoons, probably executed 1776-77, see A. Kidson George Romney 1784-1802, London, 2002, no. 76.
The inscription on the reverse of the drawing suggest that the present work was executed in November 1783. Also in September 1783, Emma Hart had begun modelling for Romney in earnest and as with the subsequent oil painting, her features are discernable in the face of Comedy. We also know that during November 1783 Romney executed a series of studies of this subject in a new sketchbook, possibly intending to commence on a painting immediately.
The painting of this subject, different in composition, was completed in or shortly after 1791 for John and Josiah Boydell and exhibited at the Boydell Shakespeare Gallery. Two other versions of the painting are known, one in the collection of Lord Egremont at Petworth.
It has been suggested that Romney's inspiration for the subject was an Italian religious work such as Reni's Birth of the Virgin, which Romney is known to have studied whilst in Rome, however it is likely that Reynolds' portrait David Garrick between Tragedy and Comedy was also not far from his mind.
A pencil study for the subject is in the Folger Shakespeare Library, Washington, D.C. two preparatory studies for painting are in the National Gallery of Scotland and a pen and ink drawing of the composition but in reverse is in the Fitzwilliam Museum, Cambridge, see P. Jaffé, Drawings by George Romney from the Fitzwilliam Museum Cambridge, Cambridge, 1977, p. 37-38, no. 62.