Little is known of Modigliani's early years in Paris, except that he lived for sometime at the house of Ortiz de Zarate. The two were sitting one day on the terrace of the Café de la Rotonde, their habitual haunt in Montparnasse, when Picasso walked by, "Ortiz pointed him out as the man who had painted the startling canvases Modigliani admired. Dedo was not impressed by this fellow walking his dog - this short, squat man. Picasso was well-built for his size with full, strong features and thick, shiny black hair. One thick lock of hair cascaded from under his ugly workman's cap over one eye. He looked nondescript in his patched and faded blue overall." (P. Sichel, Modigliani, London, 1967, p. 79)

By this time Montparnasse had been discovered by artists from all parts of the world. It had superseded Montmartre as the centre for intellectual life. The Closerie des Lilas, as well as the two famous cafés, La Rotonde and Le Dôme, were the meeting places for painters and poets who often engaged in heated discussion with political exiles such as Trotsky. Artists returning from the front could find their friends in those café terraces. Writing about the atmosphere, Roland Penrose recalled, "The company was widely international, those in uniform such as Léger, Raynal, Braque, Derain, Apollinaire and many others mixed again with painters, sculptors and writers such as Modigliani, Kisling, Severini, Soffici, Chirico, Lipchitz, Archipenko, Brancusi, Cendrars, Reverdy, Salmon, Dalize. There was no lack of talent among them and such encounters were welcome contrast to the ceaseless roar of cannon and the stench of death not more than fifty miles from gates of Paris." (Picasso: His Life and Work, London, 1958, p. 193).

Carol Mann (Modigliani, London, 1980, p. 92) also writes, "The mood in those cafés during the war was a very particular one, as Vlaminck noted: 'The done thing was to be or at least look abnormal or strange. Everyone smoked opium, consumed hashish (hashish pills only cost 25 centimes each but few people restricted their consumption to one a day) took alcohol and ether...painters, poets, would-be writers were all poor, but it did not matter, it was not a question of who made the most money. The one thing you had to have was a ferocious sense of humour.' Modigliani was not naturally witty; he may have been too involved with expressing his own emotions to acquire the necessary distance to be able to laugh at himself. Instead, he created "un personnage", a character, recognisable at the distance by outrageous conduct - a Bohemian of the grand manner. 'It's odd but you never see Modigliani drunk anywhere but at the corners of the Boulevard Montparnasse and the Boulevard Raspail', Picasso remarked."

Despite a certain personal coolness, Picasso and Modigliani both had a great respect for each other's artistic abilities, Modigliani referred to Picasso as "always being ten years ahead of the rest of us." This awe of Picasso's perceptive and innovative artistic psyche perhaps accounts for Modigliani's inscription 'savoir' (knowing or knowledge) on this portrait. Werner Schmalenback writes, "As a rule, what he wrote on the painting was the sitter's name. Sometimes, however, he jotted down one of more words, related in meaning to the subject, as with the word savoir - 'to know', 'knowing', 'knowledge' - that he put on his portrait of Picasso.

"Here, as in many of his other paintings, Modigliani has set down the sitter's name in capital letters alongside his likeness. It may be that this habit of inscribing paintings is another sign of Cubist influence, as it is the work of such other contemporary artists as Robert Delaunay and Paul Klee. The incorporation of lettering as a stylistic device also appears in the work of some older artists, including Vincent van Gogh and, especially, Gauguin. In Modigliani it also has overtones of 'popular culture': it recalls the imagerie populaire, the woodcuts sold from foreground booths, or the broadsides sold by the street balladers still common in his native Italy. There were also precedents in so-called 'high culture'; the inscriptions on ancient Egyptian and Mexican paintings and reliefs, those on Greek vase paintings". (op. cit., pp. 29-30.)

This portrait of Picasso is one of a series of portraits of his fellow artists Modigliani painted in 1915. Following the 1914 portraits of F. B. Haviland and Diego Rivera in 1915, he also painted Henri Laurens, Leon Indenbaum, Celso Lagar, Chaim Soutine, Moïse Kisling and Juan Gris.