In 1886, Robert Henri enrolled at the Pennsylvania Academy of Fine Arts. Two years later, he traveled to Paris to continue his studies, but returned to Philadelphia in 1891 to become the leader of a group of artists that included John Sloan, Everett Shinn, William Glackens, and George Luks. Henri encouraged this group, all former illustrators for the Philadelphia Press, to apply their journalistic skills to the development of a style that could capture the vitality of the modern world.

In 1900, Henri and his followers moved to New York City, where they began to paint the city’s poorer inhabitants and lower-class neighborhoods. In their preference for these gritty urban scenes, Henri and his circle broke from the genteel traditions of the previous century and earned the appellation Ashcan School. Henri’s and the other Ashcan artists’ rejection of academic tradition and embrace of the everyday world alienated them from the leading art societies of the day. The group began to exhibit together as The Eight.

Henri was particularly interested in portraiture and early in his career had studied paintings by Rembrandt and Frans Hals. The influence of both artists is apparent in Henri’s portraits, which typically incorporate dark tonalities and a bravura handling of pigment. Many of Henri’s portraits depict unknown children of various ethnicities and social classes, such as this Romany girl. By rendering childhood innocence, Henri offered his audience a chance to sympathize with his uncommon subjects and at the same time communicated his democratic view of art and humanity.