While living in Paris Van Gogh sold few works and was supported financially by his younger brother Theo, with whom he also shared an apartment. The artist frequented the Cafe du Tambourin on the boulevard du Clichg, near his
apartment, and sometimes exchanged still-life paintings for the odd meal. The proprietress of the cafe, Agostina Segatori, is thought to be the striking woman in this painting of The Italian.
Van Gogh had also staged on exhibition of Japanese prints at the cafe in March 1887, some months before this painting was done, and it is thought through correspondence with Theo that he had embarked on a turbulent affair with Agostina. Relations with her were later cut, though the details surrounding the course of this remain unclear. At around the same time as this painting, Van Gogh had again drawn on his earlier experiences and staged the 'Impressionists of the Petit Boulevard' exhibition at the Grand Bouillon Restourant du Chalet on the avenue de Clichg. Here he displayed a number of his own paintings and also the work of Anquetin, Toulouse-Lautrec, Camille Pissarro, Gauguin, Georges Seurat, and Bernard.