When George III was asked by Lord Eglinton to sit for the most fashionable portrait painter of the day, Joshua Reynolds, he replied: ‘Mr Ramsay is my painter, my Lord.’ Reynolds tried to gain royal notice with two speculative ventures – a portrait of George III as Prince of Wales (OM 1011, 401034) and an oil sketch for a depiction of his marriage to Queen Charlotte (OM 1012, 404353) – both of which remained on his hands. Reynolds was knighted by George III, made first president of the Royal Academy and Principal Painter to the King upon Ramsay’s death in 1784, but never asked to paint anything. That the Royal Collection has a fine group of Reynolds is entirely thanks to George IV, who commissioned portraits at the end of the artist’s life and acquired many examples of his earlier work like this one. The Royal Collection contains two Reynolds portraits of George III's younger brother, Edward, Duke of York, both autograph versions of the same design and both probably bought by George IV. Not surprisingly early references to them are difficult to disentangle. The sittings for the earlier portrait (OM 1013, 403419) took place in 1763 and the head was repeated for this the later portrait of 1765 (OM 1014, 404645), though a single appointment on 13 April 1765 may be associated with this second image. The sitter is shown wearing naval uniform and a bicorne hat and tucking a horse-whip under his left arm; the portrait is enclosed within a painted oval.