Edward Hopper first visited Gloucester in the summer of 1912. Dr. Gail Levin writes, "Hopper was probably aware of other painters who had worked in Gloucester and of the town's history as a summer art colony. Beginning in the mid-nineteenth century, such artists as Fitz Hugh Lane, Sanford Gifford, William Trost Richards, Worthington Wittredge, Winslow Homer, William Morris Hunt, Frank Duveneck, John Henry Twachtman and Childe Hassam had painted in Gloucester. But the Gloucester scenes Hopper certainly would have known were those by Maurice Prendergast, who had shown along with Hopper's teacher Robert Henri n the New York Exhibition of "The Eight" in 1908. All of these artists appreciated Cape Ann for its intense sunlight, brightened by the sea, and Hopper was no exception. He was also drawn to the local architecture, which offered wooden houses in a variety of distinctive styles ranging from shacks to ornate Second Empire mansions" (Hopper's Places, Los Angeles, California, 1998, p.57).
Hopper summered sporadically in Gloucester, Massachusetts between 1912 and 1928 producing a body of watercolors, oils and drawings with the village streets and houses as their subject. These scenes of Gloucester were positively received by the public who recognized the honest portrayal of a small American town with its own particular architectural character. Lloyd Goodrich writes: "It was in Gloucester in 1923 that [Hopper] embarked on the watercolors of houses and villages streets that were to become his first generally known type of subject -for a while, one might say, his trademark. He liked the spare wooden houses and churches of the early years, their puritan severity sometimes relived by jigsaw ornamentation; or the more ambitious flamboyant mansions of the late nineteenth century with their mansard roofs, wide spreading porches and jutting dormers and bay windows. But equally he liked the poorer rundown sections the bare unpainted tenements, the jumble of sheds, privies, and the fishhouses and factories. Like every realist, Hopper loved character, and these varied structures were as exactly characterized as a portrait painter's sitters" (Edward hopper, New York, 1978, pp.53-54).
Many of the houses Hopper painted—among them Haskell's House, 1924 (National Gallery of Art, Washington, D.C.) a sea captain's Victorian mansion perched high above Gloucester's Main Street, and Anderson's House, 1926 (Museum of Fine Arts, Boston), a modest 1880s clapboard structure on a busy street—are still standing today and seem very little changed. In Houses at Gloucester the focal center of Hopper's composition is a familiar white clapboard house depicted on a nondescript street corner. The houses to the left and the continuing street to the right of the subject are cut short, giving the unpopulated scene a sense of continuity, as if it goes on interminably in either direction.
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