William Robert Hollingsworth, Jr. (“Hollie”) found inspiration in the residents and rural scenery surrounding Jackson, Mississippi. An early talent for cartooning is reflected in his portrayals of African Americans, whom he often caricatured. He painted the countryside onsite with watercolors, but like many artists, he completed his oils indoors.
Hollingsworth was born in Jackson and attended Davis School and then Jackson High School, graduating in 1928. He studied for two years at the University of Mississippi, then proceeded to the Art Institute of Chicago where he expected to study commercial art. He supported himself with illustration for magazines, book covers, and advertising. Encounters with the masterworks in the Institute’s collection shifted his focus toward painting.
Unable to maintain himself as an artist–commercial or otherwise–in the city, Hollingsworth returned to his hometown, where he found a job as a clerk with the Federal Emergency Relief Agency during the Depression. The position lasted until 1934. Afterward, supported by his wife, Jane Oakley, a fellow student he had met at the Art Institute, he painted full time. Alongside Eudora Welty, Marie Hull, Karl Wolfe, and Mildred Nungester Wolfe, Hollingsworth was active with the Mississippi Art Association, which ultimately led to the establishment of the Mississippi Museum of Art. Throughout his life, including during his most prolific artistic period, he struggled with bouts of depression. His friend Karl Wolfe gave him much encouragement: “You don’t have to live in New York or Chicago to be a painter, Hollie. You can paint by looking out the window.”
In 1941, Hollingsworth helped to establish the art department at Millsaps College, located in Jackson. With the advent of World War II, in 1942 he enlisted in the United States Navy, went to San Diego, but was discharged after two weeks; the reason given was poor eyesight. Back home he continued as an instructor at Millsaps and was an advocate for modern art which he encouraged southerners to consider. “One hears just a little too much of the jeering and scoffing which modern, top ranking American art is greeted with when exhibited in the South, and if the progressive, purely-aggressive type of art is actually being encouraged and promoted in a southern locality, then it speaks well for the advancement and awakening of the southerner to appreciation of sincere and honest art.”
At the twenty-fourth annual exhibition of the Southern States Art League Hollingsworth won the award for the best work in any medium, and with the prize money he traveled with his wife to Chicago. The excitement was short-lived; afterward, back in Jackson, he committed suicide at age thirty-four. At her death, his widow bequeathed a fund to create the William Robert Hollingsworth, Jr. Art Scholarship Endowment at the University of Mississippi Department of Art and Art History and donated three hundred paintings to the Mississippi Museum of Art.