Beginning in the late 1920s and continuing for some eight or ten years, McFee wintered at Bellevue, a former plantation in Bedford County, Virginia, where he devoted much of his energy to painting black farm workers. McFee found them to be much more interesting than professional models, and he empathized with them. As he explained, "I think I came closer to painting something of their life and my life with understanding" (quoted in Ernest W. Watson, "Still Life Paintings by Henry Lee McFee," American Artist 12 [February 1948]: 20). A maid at the plantation named Gertrude posed for Sleeping Black Girl. In it McFee succeeded in conveying the young woman’s total exhaustion through her posture. He carefully drew, corrected, and changed the figure before he began to paint "to make clear the stress and sag of the figure." McFee’s mellow palette, which gives a deep resonance to the painting, further underscores the mood of quiet sympathy. The girl’s tawny skin and the white drape determined the palette, with the greenish black wallpaper, gray head scarf, and white chair repeating the color tones. Typical of McFee’s painting technique is the delicate layering of the paint in thin, transparent layers to model the forms. Despite the solid rendering, McFee has perceived the figure and chair as large geometric shapes, and consequently the painting is at once academic and modern. Critic Arthur Millier dated the painting to 1930, which is probably too early. It was first exhibited in late 1934. As it was not shown with other pictures of similar subjects in McFee’s January 1933 exhibition at Frank K. M. Rehn Galleries in New York, it was probably painted during the following winter of 1933-34. The images of blacks exhibited in 1933 were praised for their "grave dignity and unity of effect" (Sun [New York], January 7, 1933, p. 10), and Sleeping Black Girl has these qualities. McFee considered it to be his best, if not most important, work, and was bewildered by his inability to sell it. Millier seems to have agreed with the artist, for he ranked Sleeping Black Girl the greatest American painting created in the 1930s.

Although most 1930s figure painters captured the tempo of contemporary life in the public realm, some preferred to focus on individuals in more contemplative circumstances. Among the finest of these “studio painters” was McFee. The artist had been one of the early modernists in Woodstock and New York City, but by the Depression he had begun painting more traditionally. During the late 1920s and 1930s he wintered at Bellevue, a former plantation in Bedford County, Virginia, where he depicted black farmworkers in a series of paintings that are among the most sensitively rendered portraits of Afro-Americans of the era. A maid named Gertrude posed for Sleeping Black Girl. McFee conveyed her exhaustion through subtle treatment of her posture which he redrew many times to “make clear the stress and sag of the figure.” McFee’s skill as a colorist is seen in the nuances of her soft, tawny skin. He applied paint in thin, transparent layers, so the image shimmers with delicate color, enhancing the figure’s quiet dignity. Although the work was widely exhibited, and was shown at the 1939 New York World’s Fair, it was unsold when McFee settled in Los Angeles in 1940. On October 15 of that year the Los Angeles Times art critic Arthur Millier called it the finest American painting of the 1930s, and shortly thereafter it was purchased by a local collector. McFee seems to have taken a metal-leaf frame, painted it, then scraped off some of the pigment to give it an aged look. The green tone continues the palette of the portrait, demonstrating the Arts and Crafts idea that frame and painting were mutually dependent.