In 1953, Thomas Hart Benton was commissioned by the motion-picture company Norma Productions to create a painting for the film The Kentuckian (1955) starring Burt Lancaster. Lancaster played the frontiersman Big Eli Wakefield, who decides to leave Kentucky in the 1820s to move to Texas with his little son, Little Eli played by Donald MacDonald. To capture the spirit of the film, Benton read the script and spent several days watching the filming on location in Rockport, Indiana. The preparation for the painting was extensive: Benton created numerous drawings, one of which was a cubist diagrammatic study, oil studies, and a clay model of the boy’s figure. After these preparations, he began painting The Kentuckian (1954) in his studio in Kansas City.

The painting is based on one of the scenes from the film, in which Big Eli and his son discover a frontier village. The artist turned the horizontal frame of the screen to a vertical frame which shows the courageous backwoodsman in full figure walking westward. The figure is on a hill heading toward an unseen village, located somewhere in the sunny valley. This subject appealed to Benton, who explored themes of the American West and the progress of civilizations in his early murals, such as America Today (1930-1931). In The Kentuckian, Benton creates a quintessential representation of the frontiersman, as he breaks new ground and leads his family to the golden land in the West. By using a baroque compositional device, the diagonal position of the boy and dog, Benton places greater emphasis on the dynamic vitality of the Kentuckian. The painting shares characteristics with Benton’s later easel portraits, such as New England Editor (1946) and Portrait of a Musician (1949). In these portraits, Benton focused more tightly on a large single figure and uses bold colors to create forms with crisp outlines.

The painting was the centerpiece of the film’s one-sheet poster which had the inscription: “A great artist depicts a great American motion picture” with Benton’s name underneath. Throughout his career, Benton had a longstanding relationship with Hollywood and the film industry. In 1937, he was commissioned by Life Magazine to paint his famous work Hollywood (1937). In the next decade, he visited Los Angeles many times and was commissioned by studios to create works that were used as film advertisements. One of the best-known examples is the lithographs he created in 1939 for the film The Grapes of Wrath (1940). The Kentuckian was Benton’s last major Hollywood commission, and it quickly achieved the iconic status that extended beyond the film industry. The image proved a commercial success and was reproduced on labels for Bean’s Choice whiskey bottles. It was also satirized in the American animated sitcom The Simpsons in which Mr. Burns is reimagined as the Kentuckian frontiersman. The painting was exhibited for the first time at the film’s premiere in Washington D.C. After that, it was not exhibited in public until 1978, when it was donated to the Los Angeles County Museum of Art.