Robert Henri dedicated his career to painting portraits of those he called “my people,” namely, sitters who evoked a personal response in the artist. He found many appealing subjects while traveling in Spain, including matadors and picadors, gypsies, dressmakers, and performers. Henri admired the subject of La Madrileñita, a 15-year-old dancer named Josefa Cruz, for her talent and traditional training, as he later recalled: “Although very young she was already a very remarkable dancer at the time the painting was done, and it seemed to me that she had in her carriage . . . much of the spirit and dignity of old Spain.” Henri painted sixportraits of Cruz; in this version, completed over the course of two days, she turns her head to look over her shoulder, directly engaging the viewer in a poised and assured manner. Her enigmatic smile bears a sense of mystery that is heightened by the darkness beyond.