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The sitter in Kramer's 'Portrait of a Gypsy' is his sister, Sarah (who married the artist William Roberts). She recalled starting to sit for her brother when she was thirteen, 'usually done up as a Gypsy girl. He did lots of pastels which were bought as they were done by a firm in Bradford called Matthews and Brooke, and the proceeds from these seemed to keep all of us although they were only about a pound a time. Jacob was easy to sit to and the sittings did not last long; but though so many were produced they are now difficult to find' (Sarah Roberts, 'Memories of Jacob', in 'Jacob Kramer reassessed (London: Ben Uri Gallery, 1984), p. 15). The gypsy motif had been popularised by Augustus John, particularly in his studies of his partner and muse Dorelia McNeill, and expressed a longing for the freedoms of a pre-industrial age.

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