American portrait artist Dorothy Hart Drew was born in Ethel, Missouri in 1910, a great-niece on her mother's side of American sculptor Joel Tanner Hart. Her sister Lorna enjoyed a local reputation as a child prodigy on the piano after the family moved to St. Louis in 1914. Apparently in search of opportunities for Lorna, mother and daughters left for New York in 1927, but their focus seems to have shifted to fostering Dorothy's early talent for drawing and painting. Dorothy studied at the New York Art Students' League in 1928, where her teachers included George Bridgeman, Ivan Olinsky, Alexander Abels, Raymond Nelson, and Sidney Dickinson.

In 1929 Dorothy Drew passed the examination for admittance to the National Academy of Design, where she won the figure painting prize in 1932, the first woman to do so in fifty years. The year before she had already become one of the youngest artists to have her work accepted for the Academy's annual exhibit. During her years at the Academy she supported herself by doing portraits for the covers of Time, Literary Digest, and Vision magazines.

Dorothy Drew's ambition was to be the best portrait painter in America. She said: "I want to paint people as they really are, but I want to see them at their best." Her talent was described as "decidedly decorative," her training as "solid," and her work as "forthright and thoroughly capable." Her style was academic. Drew herself was open-minded about the art world, saying that although she disliked fads, she still found modernist trends of value for increasing public awareness of art and inspiring conservatives like herself to do their best work.

Drew's one-woman shows included that at New York's Findlay Galleries in 1937, one for the Society of Virginia Women in New York, held at the Waldorf-Astoria Hotel, and another at Stedman House in Pennsylvania. She exhibited in group shows at Grand Central Art Galleries, the National Arts Club, and the Wolfe Art Club, all in New York City. She was especially successful in attracting portrait clients from the Roanoke, Virginia area, which she visited several times.

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