In his painting, Guy Pène du Bois presented witty and mocking views of New York society. Born in Brooklyn, N.Y., Pène du Bois showed a talent for drawing during high school and in 1899 enrolled in the New York School of Art, where his teacher was William Merritt Chase. He later trained with the realists Kenneth Hayes Miller and Robert Henri. Pène du Bois went to Paris in 1905, where one of his paintings was shown in the Salon, but returned to New York following his father's death in 1906. It fell to him to support his family, so he found a job as an illustrator and as a music and art critic for the New York American, his father's former employer. Pène du Bois advocated for the new movements in art, including publicizing the 1913 Armory Show in a special issue of Arts and Decoration magazine, which he edited. Throughout his career, he both painted and wrote about art and was regarded as an astute critic. He was a member of the Society of Independent Artists, where his work was frequently included in exhibitions, and the Whitney Studio Club, where he had his first one-person exhibition in 1918. To supplement his income, Pène du Bois began teaching in 1920 at the Art Students League, and in the 1930s he founded an art school in Stonington, Connecticut, where he spent his summers.
Early in his career, Pène du Bois abandoned the dark palette and quick, gestural brushstrokes of his teachers Chase and Henri and developed a style dominated by simplified and stylized figures, depicted with a laconic eye and sharp awareness of the pomposity and artifice of social encounters. His paintings were critically acclaimed, and Duncan Phillips praised him as "an irrepressible mocker of human absurdity and a clever satirist of types familiar to our modern world." Phillips also appreciated Pène du Bois's gift for color and "flair for good painting," referring to the artist as "A remarkably able draughtsman, he is also a fine painter with a deft and confident plastic power. ...There is a clearness and a resonance in his pinks, blues, scarlets, and blacks." Duncan Phillips not only admired Pène du Bois's paintings, having purchased four canvases for the collection, but also was a fan of the artist's criticism and essays on modernism and modern artists.