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In the early twentieth century, scores of artists came South as curious tourists, or as seasonal visitors escaping the cold, or as soldiers stationed at the many military bases that peppered the region. Others were associated with educational initiatives, particularly the effort to provide quality schooling to the South’s underserved African American population. It was for this reason that, in 1917, Sidney Dickinson joined members of his family in rural Lowndes County, Alabama, where his maternal aunt, Charlotte Thorn, had established the Calhoun Colored School. Following the advice of Booker T. Washington, Thorn selected Calhoun because it was a place “where the people were most in need.” She modeled her curriculum on Washington’s approach at Tuskegee Institute, combining rudimentary classwork with manual training. Over time, the Calhoun campus became known as “the lighthouse on the hill.”

The son of a Congregationalist minister, Dickinson was born in Wallingford, Connecticut; his father’s pastoral assignments took the family to Vermont, upstate New York, and Fargo, North Dakota. Between 1910 and 1912, he studied at the Art Students League under William Merritt Chase and George Bridgman, and at the National Academy of Design with Douglas Volk. Afterward, he traveled around the country, experiencing his own wanderjahr. Dickinson’s arrival at Calhoun coincided with an agricultural downturn in the area, the result of drought, floods, tornadoes, and the boll weevil. His official role at the school is unclear; no fine art was taught, although he may have supervised mechanical drawing. Family lore suggests that he coached a baseball team. Nevertheless, Dickinson found several memorable models whom he painted with sensitivity, endowing them with a dignity that recalls old master paintings. The best-known of these is The Alabama Studio (1918), a large allegorical canvas executed in the manner of Velasquez and which was first exhibited at the Pennsylvania Academy of the Fine Arts.

Paintings dating to 1917 and 1918 suggest that Dickinson’s residence in Calhoun was limited to that two-year span. He returned to New York and joined the faculty of the Art Students League, teaching there over three distinct tenures: 1919–1920, 1939–1943, and 1949–1973. He specialized in portraiture and, for this purpose, rented studio space on West Fifty-Fifth Street, near the League and Carnegie Hall, a convenient location for his clientele. For over fifty years, beginning with a self-portrait in 1915, Dickinson regularly exhibited at the National Academy of Design, where he was awarded several prestigious prizes and accorded full membership in 1927. In 1931, he was elected a member of the American Academy of Arts and Letters. His work was also included in group presentations at other notable national museums.

Dickinson’s wanderlust suited him to the life of an itinerant portraitist, following in the tradition of nineteenth-century artists who traveled from city to city in pursuit of commissions. These commissions sometimes called him back to Alabama. In 1926, he was commissioned to do a formal portrait of Thomas Kilby, who served as Governor of Alabama from 1919 to 1923; the three-quarter length portrait still hangs in the state capitol in Montgomery. A few other paintings featured the city and surrounds of Montgomery. The Leininger Place exemplifies Dickinson’s metaphorical work of this type, drawing contrasts between the casually posed young man in the foreground and the decaying symbols of the Old South in the background, all set beneath a tempestuous sky. Scholarly attempts to identify the location and the figure have been unsuccessful. Other sitters included Fiorello LaGuardia, mayor of New York City; President Woodrow Wilson; six members of the Rockefeller family; and dignitaries at Harvard and Princeton universities, as well as numerous fellow artists. Dickinson approached his diverse subjects with equanimity: “I never start a portrait with a preconceived idea about the sitter. I feel so much may be revealed in a face. A banker: why a banker may have the quality of a poet.” He worked efficiently, painting in the alla prima (wet on wet) style, and often completed an entire sitting in a single afternoon.

In a 1927 article about his work, Dickinson expounded on his theory of painting, which serves to explain his success: “I believe in direct painting always, whether the painting is to be carried eventually to great completeness and detail or whether it is to be left a sketch or a single sitting performance because I feel that the enthusiasm and vigor of the first painting can hardly be duplicated later on in the picture. If the picture is painted in a broad and direct style at the beginning, much of the first enthusiasm will be kept on the canvas, no matter how minutely it may be finished later on.”