A member of a group of realists known as The Eight, who were interested in recording urban scenes, Shinn depicted the realities of New York spontaneously and directly. Of the four Philadelphia artists who, along with their mentor Robert Henri, comprised the nucleus of The Eight, Shinn was the third to move to New York to pursue his artistic career. He thrived on the life of the city; both his street subjects and theatrical themes speak to the changing modes of urban experience at the turn of the twentieth century in New York.
In 1899 Shinn began work on drawings for a book entitled New York by Night by William Dean Howells, a prominent novelist who sought a blend of romance and reality in his writing; Tenements at Hester Street is one of the works intended for Howells’s book. Shinn endeavored to show the more squalid aspects of New York in his illustrations. To Shinn, Fifth Avenue, known for its wealthy inhabitants and beautifully kept buildings, was artistically uninteresting. He preferred the poor, rundown neighborhoods—The Bowery, the Gas House Section, and the Lower East Side. In these poverty-stricken areas, Shinn found the people and the buildings of equal interest: the residents, mainly poor immigrants, as well as the dilapidated buildings. Tenements at Hester Street, a drawing which depicts crowded tenements— families on fire-escapes and roofs, trying to escape the heat of a sultry summer night, clustered together in run-down buildings—is said to have inspired Mrs. J. Pierpont Morgan to open a haven for the poor on the Lower East Side of Manhattan.
Shinn's work as a newspaper artist directly influenced his city images, since that work called for immediacy and spontaneity in capturing a scene. The swift execution of line and the summary treatment, nearly caricature, of the figures and buildings in Tenements at Hester Street suggest a reporter's earnest attempt to record an incident on deadline. Shinn often worked from memory; he had a flawless, nearly photographic recall and was able to retain an "on the spot" quality even while working in his studio.
In addition to its subject matter, Tenements at Hester Street shows Shinn’s radical tendencies applied to technique. He developed an unusual method, drawing with his pastels on wet paper. Through this process, when the colored pigment dried, it acquired a rough texture appropriate to the scene, rather than the soft powdery appearance ordinarily produced by pastel.