In 1973, Norman Mailer published Marilyn, a biographical profile meant to be a 20,000-word piece, but which Mailer expanded to over 100,000 words after becoming deeply fascinated with Monroe during the writing process. Marilyn would remain such a fixture in Mailer’s mind that he would also compose a fictional account of her life, 1980’s Of Women and Their Elegance, and would turn this into a play, Strawhead, which was performed at The Actor’s Studio in 1986. This chapter explores Mailer’s fascination with Monroe, which likely arises from the various ways in which aspects of his life so closely resemble those of his subject. Like Marilyn, Mailer struggled with a controversial public image that threatened to overshadow his craft and at times led to misunderstandings and reductive assumptions about his personal character.

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.