Jacques Lipchitz, born Chaim Jacob Lipschitz in Druskieniki, Lithuania, in 1891, moved to Paris in 1909 with his mother's support to study at the École des Beaux-Arts and the Académie Julian^[1]. He formed friendships across the international School of Paris, including Brancusi, Modigliani, Soutine and Archipenko, and it was his 1913 encounter with Picasso that pushed his sculpture towards Cubism^[1]. From 1916 he was represented by Léonce Rosenberg's gallery, the same dealer who showed Picasso, Braque and Gris. Modigliani's own list of close friends in this period is recorded as beginning with Max Jacob, Lipchitz and the Portuguese sculptor Amedeo de Souza Cardoso, later widening to include Soutine, Utrillo, Pascin and Kisling^[2]. The two men moved in overlapping Montparnasse circles for years before Modigliani painted this portrait.

The bulk of Modigliani's surviving paintings date from 1916 to 1919, following several years in which he concentrated almost entirely on carving stone heads and figures^[2]. His portraits of this period typically combine two viewpoints in one face, a frontal pose for the body merging with a lateral view of the features, a device the artist used consistently and one that echoes the multi-angle approach of Cubist portraiture without adopting its fragmentation outright. It was around this same year that Modigliani painted friends and acquaintances directly, working quickly and often in a single sitting, a practice that shaped the informal, close-quarters intimacy of his double portraits.