The extent to which Bolling was aware of or participated in this intellectual and critical debate about African American art is unclear. He repeatedly stated that he created his sculptures for his own pleasure. Bolling produced sculptures that confronted prevailing black stereotypes. He depicted African Americans working at their daily jobs or enjoying a moment of leisure, and his nude figures emphasize the beauty of the human form. The sculptures demonstrate an easy naturalism in their gestures and movement. Figures shift their weight to one leg as they wash or iron clothes or stride with their arms swinging slightly as they balance their loads.
Critics applauded what they perceived as the lack of symbolism and sentimentality in the sculptures and appreciated his mastery of woodcarving techniques. Although white critics complimented Bolling on his ability to capture motion and expression, they also attributed humor to the artist as a racial characteristic. Notices of his work in African American newspapers and magazines, however, regarded the sculptures as conveying sympathy and dignity to black workers and occupations.
Nevertheless, Bolling’s work in wood and in small scale confounded some art professionals. In 1938, at the request of the Harmon Foundation, Bolling sent two sculptures to the Baltimore Museum of Art. When the curator rejected his work as "applied art," Bolling wrote a letter to Evelyn Brown at the Harmon Foundation in which he demonstrated that he understood the difference between "fine" and "applied" art.
"Applied Art is that art which has a use or can be used. . . . Fine Art is that art which has no use, save its esthetic value and beauty, the size of the work has nothing to do with whether it's applied or fine arts. . . . Connoisseurs both in America and a broad [sic] have my works in their collections as fine arts, in 1934 I was listed as an American Sculptor,-medium Wood carving. . . . I am of the opinion that [the curator] doesn't know very much about art."
Leslie Garland Bolling to Evelyn S. Brown, 27 March 1939, Harmon Foundation Papers, Library of Congress.