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Well before David Fredenthal (1914-1958) was thirty, he already had two successful solo exhibitions at the Downtown Gallery in 1937 and 1938; received a MoMA fellowship to study in Italy; and was awarded a two-year Guggenheim Fellowship. In early 1940 while in Colorado finishing his Guggenheim Fellowship, Fredenthal learned Erskine Caldwell, author of Tobacco Road, had seen his paintings of factories and tenements in a recent exhibition at Columbia University and suggested Fredenthal should illustrate the deluxe edition of his novel to be published by Duell, Sloan & Pearce.

This news caused Fredenthal to head to Caldwell's hometown of Wrens, Georgia, where he introduced himself to Caldwell's father Reverend I.C. Caldwell. Fredenthal's companion on this adventure was Charles Shannon, an artist raised in Alabama who had received a Rosenwald Fund, traditionally a grant for African-American artists, to paint Southerners in 1938. Reverend Caldwell showed the artists around the area and introduced them to local sharecroppers. Fredenthal was in Georgia for two months before he returned to New York. Back home, Fredenthal then read Tobacco Road and adjusted his drawings of what he had seen to fit the story. For the final drawings, the key scenes were done in brush and brown ink for color reproduction and the remaining ones were executed in pen and black ink.

Fredenthal sent the drawings to Erskine Caldwell who convinced the publisher Duell, Sloan & Pearce they were perfect for the story. The illustrated edition was published in November 1940 and was selected by The New York Times as one of the best three illustrated books of 1941.

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