This chapter discusses the creative playfulness in the screenwriting process of Ingmar Bergman’s filmmaking. The process of writing from notes and drafts to finished screenplays is examined from the perspective of genetic criticism in combination with perspectives on screenwriting as an intermediate process across media and in stages. The notion of play refers both to Bergman’s method of creative writing and to the playful dimension of the finished artwork, i.e. the films and screenplays. Play is understood in terms of transcendence between the fictional and the real on various levels. Most importantly, the chapter focuses on play in the ambivalence of agency in Bergman’s notebooks—that is transgressions between author, narrator, and character—that continues in the aesthetics of self-reflexivity and auto-fiction in the screenplays and in the films. The Ingmar Bergman Archives, where his notes and screenplay drafts are collected and digitized, allow such an examination of the writing process. The archive consists of the donation of Bergman’s personal collection of notes, drafts, letters, and other documents—personal and professional—from his early career in the 1930s until the last productions in the early 2000s, across several media and art forms.