Jupiter and Io, 1785 by John Hoppner (English, 1758--1810)
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Jupiter and Io, 1785 by John Hoppner (English, 1758--1810)

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John Hoppner
1785
Portrait of a Lady as Evelina by John Hoppner
Dorothy Jordan
Artist: John Hoppner (English, 1758-1810)
Date: Exhibited 1791
Medium: Oil on canvas
Collection: National Portrait Gallery, London, United Kingdom
Description
Dorothy Jordan (1761-1816, was the leading comic actress of her day. She was known for roles that required her to cross-dress as a man, which was titillating for 18th-century audiences. She is shown here in the costume of a young soldier. Endless press attention fed the public obsession with her life with the Duke of Clarence, later King William IV. They lived together for 20 years, having ten children. They never married and she continued to act, often paying his gambling debts from her own income. In 1811, the duke spurned her for an official bride. Jordan died alone in France, where she fled to escape her debts.
I found this really interesting miniature by John Wright on the website for the Cleveland Museum of Art.
It's dated circa 1806-1807, when Sir Arthur Wellesley was in his late thirties, and is copied from a full length Hoppner portrait done around the same time.

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A miniature portrait of Horatio Nelson, signed and dated 1805 by Henry Bone after the portrait by John Hoppner and commissioned by the Prince of Wales (the future George IV).
John Hoppner