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.