Quentin Massys - A Grotesque Old Woman, 1515 Ceramic Ornament
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Quentin Massys painted Vieille femme grotesque (A Grotesque Old Woman) in 1515. Also known as The Ugly Duchess, it is uncertain whether this portrays an actual woman or is a satiric jab at older women who try ingloriously to recapture their youth. If it is an actual woman, the top contender for the honor seems to be the Duchess Margarete of Tyrol-Görz.