Weighing Cotton (1939) belongs to a series of three paintings, in which the artist displayed his vision of the American heartland. Like Weighing Cotton, Cradling Wheat (1938) and Roasting Ears (1938-1939) depict agriculture landscapes that fascinated Benton: “[I am] fairly obsessed with America – the Mississippi region, the Ozarks, and the places where I can see lonely plowmen, cotton pickers, river boatmen and ramshackle houses that never were much good.'' Weighing Cotton is likely based on sketches that Benton made in the summer of 1938, while he was traveling through Louisiana, Oklahoma, Missouri, Tennessee, and North Carolina.

Later, Benton created clay models of his figures, and then set them up in three-dimensional arrangements, which allowed him to observe and examine the composition from all angles. The Renaissance painter Tintoretto used a similar method to create his compositions, and Benton began this practice in 1919. In the clay study, Benton prepared the complex multi-figure composition, but he made some additions in the painting. He added a figure in the right distance and composed the scene under a wide summer sky with wooden shacks and cotton fields in the background.

Weighing Cotton shows an ordinary day in the cotton field, where workers are absorbed in their daily routine. In the 1930s, cotton was mainly harvested manually by black workers, whose wages were determined by the amount of cotton they picked. In the painting, the men work for a common purpose, filling the wagon with cotton, but they are not a team of equals. A central figure is a white man dressed in bright red clothing standing and holding a long-handled weighing pole. In contrast, the black figures are dressed in muted colors and are seen bending over dragging the heavy bags of cotton. In this way, the artist conveys the power dynamic, the white man’s authority over the black workers. However, the dominant figure is a black woman in the foreground: she is depicted from the rear looking toward the central group. Her role in the scheme is unclear, she is dressed in a white suit and is not one of the workers. It is possible she is related to one of the workers or is passing by on her way to a special event. In Weighing Cotton, as in other paintings, Benton animates the composition by repeating forms and colors. For example, he repeats the curves in the bags hanging on the shoulders of workers and pickers. Similarly, the white clouds echo in form and color the bags and rows of cotton bolls on the right.

Benton, Grant Wood, and John Steuart Curry were the dominant figures of the American Regionalist art movement. In their paintings, they depicted rural America, mainly the South and the Midwest. Their representation of America expressed a nostalgic view of the country, even though Benton believed in the objectivity of his art: “My American image is made up of what I have come across, of what was ‘there’ in the time of my experience – no more, no less”. Still, Benton’s vision in Weighing Cotton represents an idealized version of America: the conditions of black workers in the cotton fields were much harsher and severe than Benton’s depiction.