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Although it is impossible to say whether or not it was always part of the artist’s process to execute a preparatory sketch prior to painting each miniature, we do know that John Smart retained many hundreds of these sketches. A group of preparatory sketches—of which this portrait is one—descended through the Smirke family after Smart’s daughter Sarah gave a sketchbook containing preparatory portrait studies to her friend Mary Smirke, sister of the celebrated Victorian architect Sydney Smirke. This book was probably broken up around 1877 when its contents was divided between Sydney’s daughters Mary Jemmett and Mrs. Lange, whose portions were both sold at auction in 1928. <br>G. C. Williamson was the first to suggest that Smart’s sketches were well known and that they were preparatory studies for the painted miniatures. Williamson listed the names of sitters from the sketches known to him at the time, and they include a Mr. Jones, the title formerly given to the sketch here. This designation was applied only to a paper backing that had been attached after the drawing had been removed from the sketchbook. There is no further evidence for this attribution, however. <br>The sketch is of the sitter’s head only, with a slight suggestion of a high stock collar. His head faces to the left, and his light hair is combed straight back with a flat curl above his right ear. He is depicted in an oval, and the background is unpainted. The number 161 is inscribed in graphite on both the front of the drawing and its paper backing. Upon removal of the paper backing in 1993, an inscription in graphite was revealed. Perhaps written in the artist’s hand, it suggests that the sitter’s name may be Mr. Shippar[d]. There are no known portraits of this gentleman.<br>The work can be dated to about 1776 because of its size, which, when painted on ivory, would have been around 2 inches in height. An inscription on the back of the drawing suggests that the miniature was to be mounted on a bracelet. To this date, the finished ivory for which this preparatory sketch was presumably undertaken has not been discovered.