Nothing in this self-portrait identifies the thirty-five-year-old Jean Dubuffet as an artist—neither the trim haircut, the white shirt, nor the brown jacket that blends into the background. Only the intense gaze of his narrow green eyes points to the deep preoccupation of the artist, then at a crossroads in his life.

One year later Dubuffet stopped painting for the second time and returned to his wine business. Dubuffet had tried various careers. In 1918 he enrolled at the Académie Julien, in Paris, yet left after six months. Subsequently, he studied art history, languages, philosophy, literature, and music. In 1923–24 he served in the military as a meteorologist and in 1924 worked as a technical draftsman in Buenos Aires. He then became a wine merchant, first in his parents' business in Le Havre (1925–30) and then independently in Paris (1930–34 and 1937–42).

In 1942, when Dubuffet resumed painting, he repudiated his earlier style. He adopted a seemingly untutored style that defied the categories of "ugly" and "beautiful" in conventional art and that he called art brut.

Dubuffet gave this only surviving self-portrait to Jean Paulhan (1884–1968), a French writer, critic, and editor. In 1946 Dubuffet again celebrated their friendship in his remarkable portrait of Paulhan also in the Metropolitan (acc. no. 1999.363.20).