These twelve canvases cover more than thirty years, and hardly two of them share a style. What holds them together is the people in them. A writer sat some eighty or ninety times for one portrait before her face was painted out, and a friend who had shot himself in a Paris café took the painter's own place in another.
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How These Were Chosen
Fame came early to this painter and never left him. Born in 1881 and at work until his death in 1973, he changed his manner again and again, from the cold blues of his early twenties to the broken planes of Cubism and the black and gray of the war years.
Style could not hold such a list together, so the rule was different. Each canvas here is one people keep coming back to, in museums, in books and in arguments, and each carries a story that the paint alone does not tell.
Most of those stories begin with someone close to him, a friend or a lover, or with a day he could date. The list runs from the least known picture to the most famous.
12. Pablo Picasso, Portrait of Gertrude Stein (1905 to 1906)

In Pablo Picasso's portrait of Gertrude Stein, the hands and the face do not seem to come from the same picture. The hands are soft and fleshy. The face above them is broad, flat and smooth under heavy eyelids, closed like carved stone. That gap between the two holds the whole story of how the portrait was made.
The sittings began in the winter of 1905 to 1906, in Picasso's studio on the rue Ravignan in Montmartre. Stein, an American writer, was then collecting modern art in Paris with her brother Leo. She later told the story of those sessions herself, in The Autobiography of Alice B. Toklas (1933), a memoir written in the voice of her companion.
By her account, the studio was crowded and heated by a red-hot stove. She posed in the large armchair seen in the picture, dressed in brown and leaning slightly forward, while Fernande Olivier, Picasso's companion at the time, read La Fontaine's stories aloud. She counted some eighty or ninety sittings.
In the spring of 1906, after all that posing, Picasso painted out the whole head. "I can't see you any longer when I look," he told her, in Stein's account. That summer he left for Gósol, a remote village in the Catalan Pyrenees, and on the day he returned to Paris, before seeing Stein again, he painted the head back in from memory.
The new face owed something to a discovery made that same year. At the Louvre, Picasso had found ancient Iberian sculpture from Spanish sites such as Osuna and Cerro de los Santos, and the Met links the mask-like face and heavy eyelids to that encounter. The hands were kept from the sittings, and the face came from the stone.
People said the portrait did not look like her. Picasso had his answer ready, and Stein records him giving it to Alice Toklas at her first dinner in Stein's home: "everybody says that she does not look like it but that does not make any difference, she will."
At a Glance
Artist: Pablo Picasso (1881 to 1973)
Painted: 1905 to 1906
Medium: Oil on canvas
Size: 100 × 81.3 cm (39 × 32 in)
Where to see it: The Metropolitan Museum of Art, New York
11. Pablo Picasso, Boy with a Pipe (1905)
Roses crown a teenage boy in blue work clothes, an odd ornament for a young worker holding a pipe. Behind him, the wall is painted with two large bouquets. When Pablo Picasso painted the boy in 1905, at the Bateau-Lavoir, the run-down building in Montmartre where he lived and worked, there were no roses at all. The canvas then sat untouched for a month, until one night he walked out on a group of friends in the middle of a discussion.


