Published to accompany the exhibition of the same name held at The National Gallery, London, 16th March-11th June 2023.

Includes bibliographical references.

Focusing on one of the most recognisable Renaissance portraits, this publication repositions Quinten Massys's 'The Ugly Duchess' within its original context, epitomising as it does the Renaissance's taste for satire and fascination with the 'grotesque'. 'The Ugly Duchess' celebrates Massys's leading contribution to the rise of secular and satirical painting and explores the possibility that he drew inspiration from Leonardo da Vinci's drawings. Examining the portrait alongside that of her male companion reveals the period's complex attitudes towards women, age and power. The Duchess's exaggerated facial features and inappropriate clothing may suggest that Massys is inviting us to laugh at the woman's self-delusion, but a closer reading reveals both an individual defiantly flouting convention and a painter subverting artistic expectations.