As a child, Winslow Homer was encouraged in art by his mother, a talented watercolor painter who sent her work to professional exhibitions. Otherwise, he was essentially self-taught. He never graduated from high school, but worked as an apprentice in a lithography firm in Boston and then supported himself as a commercial artist in New York. In the 1860s he became one of the most popular American illustrators, producing designs for Harper's Weekly and other magazines that presented an optimistic picture of American rural life. He began to make paintings in 1862, but it was not until 1874 that Homer largely abandoned illustration and began to support himself chiefly by selling his oils and watercolors.
In 1881 Homer left the United States to work for two years in England, where he settled in the tiny fishing village of Cullercoats on the eastern coast. This period has generally been viewed as the turning point in his career, for it is when he first began to deal with marine subjects and to express a new seriousness of mood. On his return to the United States Homer settled not in New York but at the remote village of Prout's Neck on the coast of Maine, where he spent the remainder of his career. From this point on, Homer saw little of artists in New York and grew increasingly eccentric and reclusive. Prolific in watercolor, Homer created oil paintings slowly, seldom completing more than two or three in a year and producing none at all between 1887 and 1889 and between 1905 and 1908. Homer's canvases usually dealt with scenes of hunting or fishing or with life in the wilderness or at sea; they were remarkable for their emotional power and strength of design. By the time of his death in 1910, Homer was widely regarded as the greatest American painter of his time.
Homer's The Wreck (1896) (96.1) won the Chronological Medal in the first Carnegie International exhibition and was the first painting purchased for Carnegie Institute. Homer served twice on the jury of the International exhibition, in 1897 and in 1901, though he was never a juror for any other institution, and he became a close friend of the museum's first director of fine arts, John Beatty, who wrote a memoir of Homer that was printed in Lloyd Goodrich's 1944 monograph on the artist.
Winslow Homer once told Charles R. Henschel of M. Knoedler and Company, a dealer who handled his work, "You will see, in the future I will live by my watercolors." Today, Homer is generally recognized as the greatest American watercolorist, and this is the medium in which he made his most original contributions. One of the first to appreciate the significance of Homer's works of this type was John Beatty, who organized an exhibition for Carnegie Institute in 1917 of watercolors by both Homer and John Singer Sargent. Beatty particularly admired Homer's tropical scenes, which he once termed "the most amazing watercolors ever produced in this country." Curiously, however, the two watercolors by Homer that Beatty purchased for Carnegie Institute are relatively subdued in color and conservative in technique.
Although it is dated 1892, Watching from the Cliffs does not relate to Homer's Adirondack and Florida watercolors of that period but returns to a subject dealt with in the watercolors made in England a decade earlier. Indeed, the central motif in this work, a woman with a child, occurs in an 1881 watercolor once owned by E. K. Warren. In that work the foreground was a grassy hillside with the same slope as in this one. The use of opaque white in Watching from the Cliffs is highly unusual for Homer's work of the 1890s and is not generally found in his watercolors on white paper after the English period. The design also contains one odd inconsistency: the women's garments are shown swirling to the right, but the smoke from the house in the distance is shown blowing to the left.