Charles Baskerville Jr. was born in Raleigh, North Carolina, but moved with his family to New York as a child when his father (and namesake) was hired as a chemistry professor at the College of the City of New York. After high school, Baskerville enrolled at Cornell University in hopes of becoming an architect. There, in addition to his major studies, he gained practical experience as the art director of both the university’s yearbook and its satire magazine, The Cornell University Widow. Though his focus eventually shifted to painting, Baskerville would routinely turn to book and magazine illustration as an artistic outlet throughout his career.

Baskerville’s studies were interrupted in 1917 when the United States entered World War I. In July of 1918, the young lieutenant was injured in combat, resulting in a brief hospital stay. During his convalescence, Baskerville passed the time by making sketches that were later published in Scribner’s Magazine. These drawings included images of his comrades at rest, injured troops, and scenes of soldiers in the midst of the very conflict that had resulted in his own injury, according to the magazine. Twelve days after his initial injury, Baskerville was exposed to gas in a separate skirmish, which left him shell shocked and incapacitated, resulting in an honorable discharge that earned him a Silver Star for gallantry in action.

After his graduation from Cornell in 1919, Baskerville pursued work as a commercial artist and portrait painter in New York. As a contributor to The New Yorker, he wrote and illustrated a popular nightclub column under the pseudonym “Top Hat,” resulting in widespread recognition throughout the city and increased portrait commissions. As a portraitist, Baskerville was sought out by an elite clientele that included an impressive roster of influential citizens, from business executives and socialites to actresses and foreign leaders.

Baskerville was also extremely prolific as a muralist and a painter of still lifes, such as Yellow Apple. His mural work surely benefitted from the connections he made as a portraitist, because the commissions were often located in the kinds of spaces that his patrons—especially wealthy women and military officials—frequented. For instance, Baskerville was commissioned to paint the murals in the first-class lounge of the ocean liner SS America, the conference room used by the Joint Committee on Military Affairs at the US Capitol in Washington, DC, and the pool house at the Long Island estate of businessman and philanthropist Cornelius Vanderbilt Whitney.

Military service in World War II took Lieutenant Colonel Baskerville abroad as the official portrait painter of the United States Air Force. In that position, he created over sixty portraits of officers and soldiers that were exhibited widely during and after the war, and are now on permanent display at the Pentagon. These portraits, Baskerville said, “are what I am proudest of.” Paintings by Charles Baskerville are held in the collections of the Metropolitan Museum of Art and the Smithsonian American Art Museum.