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James Abbott McNeill Whistler, Arrangement in Grey and Black No. 1, 1871

Whistler’s Mother, or Arrangement in Grey and Black No. 1, as it’s actually titled, speaks to the artist’s ambition to pursue art for art’s sake. James Abbott McNeill Whistler painted the work in his London studio in 1871, and in it, the formality of portraiture becomes an essay in form. Whistler’s mother Anna is pictured as one of several elements locked into an arrangement of right angles. Her severe expression fits in with the rigidity of the composition, and it’s somewhat ironic to note that despite Whistler’s formalist intentions, the painting became a symbol of motherhood.
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Sandro Botticelli, The Birth of Venus, 1484–1486

Botticelli’s The Birth of Venus was the first full-length, non-religious nude since antiquity, and was made for Lorenzo de Medici. It’s claimed that the figure of the Goddess of Love is modeled after one Simonetta Cattaneo Vespucci, whose favors were allegedly shared by Lorenzo and his younger brother, Giuliano. Venus is seen being blown ashore on a giant clamshell by the wind gods Zephyrus and Aura as the personification of spring awaits on land with a cloak. Unsurprisingly, Venus attracted the ire of Savonarola, the Dominican monk who led a fundamentalist crackdown on the secular tastes of the Florentines. His campaign included the infamous “Bonfire of the Vanities” of 1497, in which “profane” objects—cosmetics, artworks, books—were burned on a pyre. The Birth of Venus was itself scheduled for incineration, but somehow escaped destruction. Botticelli, though, was so freaked out by the incident that he gave up painting for a while.
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Georges Seurat, A Sunday Afternoon on the Island of La Grande Jatte, 1884–1886

Georges Seurat’s masterpiece, evoking the Paris of La Belle Epoque, is actually depicting a working-class suburban scene well outside the city’s center. Seurat often made this milieu his subject, which differed from the bourgeois portrayals of his Impressionist contemporaries. Seurat abjured the capture-the-moment approach of Manet, Monet and Degas, going instead for the sense of timeless permanence found in Greek sculpture. And that is exactly what you get in this frieze-like processional of figures whose stillness is in keeping with Seurat’s aim of creating a classical landscape in modern form.
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Pablo Picasso, Les Demoiselles d’Avignon, 1907

The ur-canvas of 20th-century art, Les Demoiselles d’Avignon ushered in the modern era by decisively breaking with the representational tradition of Western painting, incorporating allusions to the African masks that Picasso had seen in Paris's ethnographic museum at the Palais du Trocadro. Its compositional DNA also includes El Greco’s The Vision of Saint John (1608–14), now hanging in the Metropolitan Museum of Art. The women being depicted are actually prostitutes in a brothel in the artist's native Barcelona.
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Vincent van Gogh, The Starry Night, 1889

Vincent Van Gogh’s most popular painting, The Starry Night was created by Van Gogh at the asylum in Saint-Rémy, where he’d committed himself in 1889. Indeed, The Starry Night seems to reflect his turbulent state of mind at the time, as the night sky comes alive with swirls and orbs of frenetically applied brush marks springing from the yin and yang of his personal demons and awe of nature.
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