In Portrait of Picasso as a Young Man, Mailer attempts to make sense of the life of a painter he deemed one of his greatest influences. In Advertisements for Myself, he included a short piece called “An Eye on Picasso,” and had also planned to pen a biography of Picasso as early as 1962. Moreover, Mailer himself also dabbled in the visual arts, producing a number of sketches that invoke a Modernist aesthetic in their relative abstraction. This chapter traces these connections, and illuminates the role that Cubism played in determining the shape and dimension of Mailer’s literary canon during the second half of the twentieth century.