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The term Ashcan School, first used retrospectively by Holger Cahill and Alfred Barr in 1934, was loosely applied to American urban realist painters. Specifically, it referred to those members of The Eight, a group who after 1900 began painting ordinary aspects of city life. The group coalesced in Philadelphia around 1891 when Robert Henri attracted artist-reporters and newspaper illustrators around him. Henri, John Sloan, William J. Glackens, Everett Shinn, George Luks, Ernest Lawson, Maurice Prendergast, Arthur B. Davies, and later, George Bellows, were the informal core of painters who reacted against prevailing restrictive traditions and academic exhibition procedures.

Following consolidation of the five boroughs into New York in 1898, the city's transformation from a 19th-century manufacturing center and seaport into a 20th-century commercial metropolis occurred alongside population growth from immigration and migration, a subway infrastructure that promoted the movement of people and goods, and the consequent shifting of commercial and residential boundaries. The resulting sprawl led to increasing illegibility; the city evolved into a totality that was nevertheless composed of neighborhoods, subdivided into enclaves segregated along class and ethnic lines. Ashcan painters believed that the city was made more knowable by discerning the totality in each fragment and the group emphasized the street over the panorama, the local over the universal, domesticating the city by representing localities where life was distinguished by intimate knowledge of immediate surroundings. Painters selected just enough from the web of overlapping edges to suggest what they took to be the city.

The beginnings of industrialization and urbanization were ignored by the majority of painters, but modernization after 1900 inspired and affected American Impressionists and the Ashcan School. Mass immigration led to social, class, and ethnic tensions, and economic depression and industrial unrest contributed to a desire among cultural producers to promote and maintain a sense of a unified, harmoniously ordered world. Documentary photographic realism is almost entirely absent from painting until the emergence of the Ashcan School and even then, most painters, with the possible exception of Sloan, celebrated the vitality of the lower classes rather than criticizing their living conditions.

While pursuing themes similar to those of the Impressionists, Ashcan painters chose not to celebrate architectural transformation but to portray the city from the street up, and despite stylistic divergence, they shared a preference for a worm's-eye perspective. They presented the city as a mosaic of little worlds and communities, using a dark, subdued palette, resulting from Henri's trip to Europe, where he was influenced by Francisco José de Goya, Diego Velazquez, Franz Hals, and Édouard Manet. Ashcan paintings are fluid and spontaneous, very different from the polish of the work done in American academies at the time. Rapid handling of thickly applied paint left individual brushstrokes, but despite its apparent spontaneity, most Ashcan art is a carefully composed synthesis by a less than objective interpreter who, through careful, selective omission, arrived at a distanced and detached viewpoint.

Just as representations of the “ideal” city were believed to help assimilate immigrants, architects and planners claimed that public works as symbols of civic unity would enhance the city and Americanize a fragmented population. Despite its planned grid, the reality of New York's disordered chaos inspired Ashcan artists. The idea of New York as a City Beautiful was stimulated by pictures; magazines were illustrated with drawings while plans show open vistas and city functions separated and partitioned. Although considered more realistic, photographers were still selective, and they depicted the city as chaotic and illegible.

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