Gertrude Stein was a key figure in Modernism, one of the most volatile and experimental periods of Western visual arts. There are very few common links between the visual artists associated with the Modernism, and this is partially due to the movement’s emphasis on experimentation between the 1890s and the 1930s. The period marked a deliberate break from artistic tradition, and many artists attempted new styles simply because they differed from what came before. Pablo Picasso, for instance, went through six distinct styles between 1901 and 1929. These include the Rose Period (1904-1906), during which Picasso painted his portrait of Stein, and Picasso’s Analytic Cubism (1909-1912).

Analytic Cubism has a massive influence on Stein’s work. It continued to influence her even after Picasso moved on to Synthetic Cubism (1912-1919) and Neoclassical works (1919-1929). Analytic Cubism is a style developed by Picasso and Georges Braque that attempts to take apart objects and analyze their shapes and individual components. Stein took up this Cubist approach in her literary portraits. Stein aimed, in part, to make literature a spacial art. Though Stein cannot use colors or shapes to depict her subject in “If I Told Him,”she uses words to a similar end.