The subjects of the painting are Jacques Lipchitz and his wife Berthe. Jacques Lipchitz was a Lithuanian cubist sculptor and a close friend of Modigliani.
Lipchitz and Modigliani first met in France at a young age and were both of Jewish descent so naturally formed a close friendship as they moved in the same circles within the Paris art community.
Modigliani and Lipchitz were some of the first artists to move to the Parisian neighbourhood of Montparnasse which gradually became the epicentre of artistic activity in the city until 1939 and the outbreak of war.
Lipchitz commissioned the painting to commemorate his wedding to the Russian poet Berthe Kitrosser whilst also knowing that Modigliani was struggling financially. Lipchitz saw it as a way to help out his friend Modigliani and agreed on a sum of ten francs for each sitting along with any alcohol he wished to drink whilst working.
The sittings for the painting took place at the Lipchitz residence at 54 rue de Montparnasse, a flat previously occupied by the artist Constantin Brancusi. Modigliani made several sketches prior to the first sitting and on the first day produced twenty drawings of which a few survive to this day. The pose in the painting was inspired by a wedding photograph of the newly wed couple.
Modigliani actually claimed to have completed the work after the first day, but Lipchitz encouraged him to keep working so he was able to pay Modigliani a higher price for the completed piece. The painting took two weeks to complete which for Modigliani was an unusually long time for once piece of work.
Following the death of Modigliani to tuberculosis in 1920, Lipchitz had to trade the painting for the return of some of his own sculptures from a dealer. The piece sold in 1922 and found a home in the Art Institute of Chicago as part of a collection assembled by Frederic Clay Bartlett in memory of his wife Helen Birch Bartlett.