I n 1905, when the American writer Gertrude Stein sat down in Paris to be painted by a then relatively unknown 24-year-old Pablo Picasso, the sitting did not unfold as one would have expected from the young prodigy. As Picasso worked, he became increasingly frustrated. He found Stein’s presence seemingly impossible to capture and soon abandoned the canvas, fleeing back to his homeland of Spain.
Yet, upon returning to Paris, he faced the portrait once more, this time alone. He completely reworked Stein’s face, transforming it into something almost unrecognizable—it looked like a mask. Stein, after seeing the final version for the first time, voiced to Picasso that she did not feel the portrait looked like her. He famously responded: “It will.”
The young Picasso’s struggles to render the Stein portrait, now housed in the Metropolitan Museum of Modern Art in New York, speaks to the complex relationship that emerges when two creative geniuses come together. For a painter, a writer is a subject that offers both intrigue and intimidation, for the task of grasping the depths of their mind is a daunting one.
In many ways, the wordsmith has the upper hand: the written medium is an unlimited resource, allowing them to flesh out their characters with as much complexity as they wish.
The painter, by contrast, has just a single frame to leave an enduring impression.
The thirteen portraits that follow capture a series of encounters between some of the most renowned artists and writers of the 19th, 20th and 21st centuries. Each painting holds its own story, woven with threads of obsession, rivalry, passion and intrigue. Some portraits have been crafted to perfection, others left unfinished, but within each, two formidable egos collide.
