Culture  /  Art History

How a Maverick Hip-Hop Legend Found Inspiration in a Titan of American Industry

When LL Cool J sat for his portrait, he found common ground with the life-long philanthropical endeavors of John D. Rockefeller.
Portraits/Smithsonian

The rapper spoke with the museum’s director Kim Sajet and the renowned British art historian Richard Ormond joined in the discussion, sharing his thoughts as part of the podcast series, Portraits. The segment is entitled “The Rockefeller Pose.”

As the foremost portraitist of his time, Sargent painted Rockefeller in 1917, about seven years after he had turned away from portraits to concentrate on painting landscapes. Ormond, who is Sargent’s grand-nephew and an expert on his work, says Sargent made the shift from portraits because of “the strain of being at the top of the tree. . . . Each time, you’ve got to go one better, one better.” However, when a Rockefeller son sought a portrait of the man who turned Standard Oil into an empire, the artist reluctantly agreed because he considered Rockefeller a visionary. In his portrait, the corporate czar sits in a chair with one hand splayed and the other clenched. Sajet suggests that one represents the tight-fisted businessman, while the other is open as if in the act of giving through philanthropy, and Ormond agrees. Sargent gave his $15,000 commission for the portrait—equivalent to more than $300,000 in 2020 dollars—to the American Red Cross as soldiers fell on the battlefields of World War I.

Wiley depicts LL Cool J in a similar pose; but there the similarity between the two images ends. While the elderly Rockefeller appears against a dark field, the middle-aged rapper and actor is pictured before an eye-catching pattern. Ormond says that Wiley’s background “leaps out at you” and “causes my eyes to vibrate.” Nevertheless, Ormond sees the portrait as “a power image.”A family crest, which Ormond calls “a very witty touch,” is topped with a Kangol knit cap, one of LL’s trademarks. It also contains boxing gloves to represent his hit, “Mama Said Knock You Out,” and his family’s history in boxing. (His uncle, John Henry Lewis was the first African American light heavyweight champion.) Centrally located is the image of a boombox, which LL says “symbolizes all things that hip-hop was and is. The music that came out of the boombox was timeless and classic.” This is not “a faux European crest,” says the rapper. “That thing is very real.” It represents both James Todd Smith, the artist’s original identity, and his pseudonym, which he adopted when he was 16. It stands for “Ladies Love Cool James,” and over the years of his career, women have remained the heart of his fan base. “Men are little more than chaperones” at an LL Cool J performance, the New York Times has reported.

Ormond, who had never heard of LL Cool J before seeing this painting, says that “it’s only recently that I really got hip with rap.” After viewing the portrait, he sees the work as Wiley’s “challenge across time” to Sargent. He credits the young and successful artist with “appropriating the great tradition of portraiture, which is what the Rockefeller comes from.