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In the field of American painting, both brothers collected the work of certain artists in considerable depth. Winslow Homer particularly appealed to them—in total, the brothers acquired over twenty paintings by the artist. Sterling called Homer one of the "best artists of the nineteenth century" and considered his Homer paintings, drawings, and prints among the highlights of his collection. Sterling also acquired a remarkable suite of paintings by John Singer Sargent, while Stephen preferred the stark realism of Thomas Eakins and contemporary artist Edward Hopper. In collecting American paintings, Sterling maintained his usual low profile, but Stephen often collected with an eye toward donating them to museums. As he stated of Eakins's paintings, "it will be my aim to provide for their ultimate disposition in a way that will promote Mr. Eakins's fame for posterity," and he donated works by Eakins and Hopper to burgeoning institutions like the Addison Gallery of American Art and the Museum of Modern Art in New York.
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