Dr. Drew was a physician and surgeon who with a partner had developed an elixir called Tonga. He apparently suffered a severe stroke or other illness when Dorothy was very young, but survived several years against all odds, finally succumbing when Dorothy was nine years old. This experience with their husband and father's health problems strengthened the Drew women's deep faith in Christian Science.

Mrs. Drew was a dedicated teacher of piano and a niece of prominent American sculptor Joel Tanner Hart of Kentucky. From an early age both of her daughters exhibited great artistic talent, Lorna in music and Dorothy in painting and drawing. (Helen Borgsteadt, too, was a talented pianist and piano teacher.) After the family moved to St. Louis in 1914, their lives seem to have revolved around Lorna's renown as a child prodigy, and they eventually went to New York in 1927 in search of opportunities for her. Their focus seems to have shifted fairly early, however, to fostering teenaged Dorothy's attempts to perfect herself as a portraitist. A letter of June 1945 from Mrs. Drew to Lorna explains the "partnership's" decision to securely launch Dorothy on her career before turning its attention once again to Lorna's aspirations. That this approach occasionally produced some friction among the women is evident from this same letter.

Dorothy studied at the New York Art Students' League in 1928. Among her teachers were George Bridgeman, who specialized in life drawing, Ivan Olinsky, Alexander Abels, Raymond Nelson, and Sidney Dickinson. In 1929 Dorothy passed the examination for admittance to the National Academy of Design, the foremost American school of conservative art. Here she won the figure painting prize in 1932, the first woman to do so in fifty years. In 1931 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 Dorothy supported herself by doing portraits such as those of American businessmen that appeared on the cover of _Time_, as well as work for the _Literary Digest_ and _Vision_ magazine.

Dorothy Drew received the Gold Medal of Honor given by the American Artists' Professional League in 1959 "for courageous and patriotic service to American art." She appears to have been a member of the Board of Governors of the League around this time, as well as chairman of its membership committee. She also served on the Board of Directors of the Republican Committee of 100 in New York City between 1964 and 1966.

Dorothy Drew's one-man shows included that at New York's Findlay Galleries in 1937, which contained numerous portraits of St. Louisans and attracted many Missouri patrons to the opening. Other one-man shows were held at the Waldorf-Astoria in New York City and at Stedman House in Pennsylvania. She also exhibited in group shows at Grand Central Art Galleries in New York city, the National Arts Club, and the Wolfe Art Club. Among the notables she painted or sketched were humorist Will Rogers, writer Irving S. Cobb, Socialist leader Norman Thomas, Eleanor Roosevelt, Helen Keller, RCA's David Sarnoff, actresses Lillian Gish and Virginia Mayo, John Dewey, President of the New York Stock Exchange Richard Whitney, and Herbert Hoover. She was especially successful in attracting clients from the Roanoke, Virginia area, which she visited several times.

Dorothy often lectured, accompanying her presentations with demonstrations of Rubens' style of portraiture. She was well schooled in the techniques of the old masters as well as the chemistry of paints.

Dorothy Drew's ambition was to be the best portrait painter in America. She summed up her artistic philosophy thus: "I am as much interested in people as in art. That is why I do portraits. 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." A review of her Findlay Galleries show in _Art News_ stated: "Portraits by Dorothy Drew at the Findlay Galleries betray the Southern background of the artist as well as that of most of her subjects. There is a dreamy, romantic quality in her interpretations of character which fits charmingly the beautiful women whom she paints. This is academic work, but the artist has a grace of style entirely her own." Other reviewers lauded her "sound characterization" and her sensibility to texture.

Dorothy Drew died in 1994; in April of that year her estate was being represented by the Catherine Shoemaker Gallery in Lambertville, New Jersey. She appears never to have married, continuing to live with her mother and sister Lorna in New York until their deaths.

In an artistic atmosphere which often dismisses the conservative style as sentimental and shallow, Dorothy Drew and her work, which she valued for its humanity and sympathy, may be out of fashion. Yet she reflected in her portraits the age-old human desire to immortalize oneself, be it in art or photographs, as well as the common yearning to surround oneself with beautiful images of beloved people and familiar places. She herself was open-minded about the art world, saying that although she disliked fads, finding "many fakirs" among their practitioners, she still found modernist trends of value in increasing public awareness of art and inspiring conservatives like herself to do their best work. Such a personality does not deserve the obscurity into which she and her work have fallen.