Modigliani and the influential Parisian art dealer Paul Guillaume became acquainted in 1914 through Max Jacob. 1914 was an important year for the artist: he had just met Beatrice Hastings, an English poet with whom who he had a stormy love affair that corresponded to a highly creative phase in Modigliani's career during which Paul Guillaume installed the painter in a Montmartre studio. Novo Pilota was done at Beatrice Hasting's place on Rue Norvins, in a house in which Emile Zola had once lived. Two oil portraits painted in 1915 show similar Cubist deformations in the face, one of which also represents Guillaume, portrayed bareheaded before an upright piano that cuts off contact with the background of the composition.
On a background made up of broad colored sections, the artist has sung the praises of the great collector of African art, aged barely twenty-three, represented as the youthful guide and guardian of contemporary painting. His last name, written in capital letters, moves out of the frame in the upper left; in the lower left are the words "Nova Pilota;" on the right, "Stella Maris." These formal inscriptions are integrated into the portrait. The signature, in small letters and carefully affixed on the lower right side, evokes the beginning of a list of artists who might be taken in hand by the young dealer. His eyes barely open to acknowledge the outside, but the gaze within them betrays his self-assurance and vitality. The Cubist nose, the half-open mouth, the well-groomed moustache, and the forward-jutting chin are all meticulous touches that contrast with the solid, polyhedral shape of the head and with the forehead partially concealed by his casually-worn hat. The sloping shoulders blur out the presence of the bust in favor of the faintly effeminate gesture of the crooked arm and of the guiding right hand.
This portrait is revelatory of Modigliani’s comfort with Cubism as well as his emphatic, assertive depiction of both the art dealer and Modigliani himself as an artist. It expresses the meeting of two contrasting personalities who nevertheless shared in the cult of modern, living art.