Harry's paintings were regularly accepted to major exhibitions in America and Europe. In 1885, at the Annual Exhibition of the National Academy of Design, his prowess as an artist garnered him one of the most prestigious awards in the art world of America, the First Hallgarten Prize, for the best picture painted in United States by an American citizen under thirty-five years of age. Moreover, Harry successfully competed for the attention of the art-buying public alongside such artists as Mary Cassatt, J. Alden Weir, Winslow Homer, James Abbott McNeill Whistler, and John Singer Sargent, in addition to Frank Duveneck, Walter Shirlaw, and William Merritt Chase, who had studied with Harry in Munich. Further confirming his standing in the art world, Harry was consistently selling his works at premium prices and was receiving frequent commissions to create paintings for a growing circle of high-society clientele.

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