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Spanish painter Pablo Picasso painted this Portrait of Gertrude Stein in 1906 after about 90 sittings. The American writer's face has a mask-like quality that anticipates Cubism. Stein reportedly said it didn't look like her. Picasso replied: "It will."
The portrait marks Picasso's transition from his Rose Period to the radical experiments of 1907. The simplified features and heavy-lidded eyes show influence from Iberian sculpture. Stein bequeathed the portrait to the Metropolitan Museum in 1946.

David Roentgen, 1776
The Metropolitan Museum of Art, New York

Ancient Greek (Unknown), -500
The Metropolitan Museum of Art, New York

Ancient Greek (Unknown), -390
The Metropolitan Museum of Art, New York

Diego Velázquez
The Metropolitan Museum of Art, New York
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