Gertrude Stein and her brother compiled one of the first collections of Cubist and modern art. She owned early works of Pablo Picasso, who became a friend and painted her portrait. At that time Picasso was neither famous nor rich. The appreciation of the Steins and their picture purchases brought a little light into the poor life of young Picasso.
She had more than 80 sittings for this 1906 portrait.
"Everyone thinks she does not look like her portrait, but never mind, she will". (Picasso)
A man once criticized Picasso for creating unrealistic art. Picasso asked him: "Can you show me some realistic art?" The man showed him a photograph of his wife. Picasso observed: "So your wife is two inches tall, two-dimensional, with no arms and no legs, and no color but only shades of gray?"