Els Quatre Gats, a tavern and cabaret opened in 1897 and consciously modelled on the artist cafes of Paris, became the meeting point for Picasso's generation of Barcelona artists, drawing in painters such as Ramon Casas and Santiago Rusinol, the sculptor Manolo Hugue, the writer Jaime Sabartes, and Sebastia Junyer Vidal himself^[1][2]. At the crossroads of that cafe, Picasso, still a teenager, developed both friendships and rivalries with older, more established artists, many of whom had already trained in Paris^[2]. It was in this setting, during the city's 1900 festival week, that Picasso staged his first one-man show, just three months past his eighteenth birthday, hanging dozens of cheap charcoal portraits that sold quickly alongside a handful of his more ambitious paintings^[2].

Before Picasso's move to Paris, he produced a substantial body of portraits of the friends, fellow artists and acquaintances who made up his Barcelona circle, a practice consistent with his documented habit of trying out different styles and subjects across this formative period^[1]. His painting Last Moments was selected to represent Spain at the Paris International Exhibition of 1900, giving the nineteen-year-old Picasso his first real reason to travel to the French capital^[2]. That October, dressed as, in his friend Jaime Sabartes's recollection, a flamboyant Spanish artist, Picasso and Carlos Casagemas took the train to Paris together, both of them well-to-do young artists from the same Barcelona milieu that produced portraits like this one^[2].

Picasso's first exhibition, in Barcelona, took place in 1900, the same year he and Casagemas first travelled to Paris^[3]. Casagemas fell into a troubled, one-sided infatuation with a model named Germaine during that Paris stay, and returned to the city alone after a period back in Barcelona, determined to win her back^[1]. In February 1901, while Picasso was in Madrid working on the short-lived art journal Arte Joven, Casagemas shot himself in a Paris cafe after Germaine rejected him again^[1]. That death, on top of the earlier loss of his own younger sister, marked Picasso deeply and became the direct catalyst for his melancholy Blue Period, the phase of his career that followed immediately after this Barcelona portrait period closed^[1].