Sir Joshua's Kitty Fisher as Cleopatra is a celebrated picture, one often taken as a representative of what are referred to as Reynolds's “courtesan portraits,” portraits of women—actresses, mistresses, models, prostitutes—who, in a variety of ways and with varying degrees of notoriety, traded sex for money. Reexamining a portrait already well known for its aesthetic, thematic, and cultural complexities, this essay considers first Reynolds's reworking of the Trevisani original and the Pliny account that inspired it. Then it reroutes all of the portrait's intricately connected themes through an understanding of Cleopatra's wager with Antony. That wager is crucial because Reynolds represents the moment at which it was won, and because Fisher is thereby asked to represent a female sexuality inextricable from the world of high-stakes gambling so important to the mid eighteenth-century England.

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