Maddonnas' 1991 film Truth or Dare, based on her 1990 “Blond Ambition” tour—itself a combination of pop music and performance art— defies easy categorization. It is a “docudrama” of sorts: part documentary, part concert film, part dramatic enactment. By combining various filmic styles and traditions. Truth or Dare recreates certain long-standing cultural dichotomies between, for instance, onstage and offstage, public and private, reality and appearance, or truth and artifice. The film replicates such oppositions only to then question their continuing validity. Binary distinctions in Truth or Dare prove more apparent than real, more fleeting than differentiating. Ultimately, I believe, the film finds such categories irrelevant, at least as far as they concern this particular cultural icon and individual. Madonna. The collapsing of long-held cultural dichotomies is a central tenet in recent formulations of postmodernism. An examination of Truth or Dare within the framework of postmodernist theorizing, in particular Jean Baudrillard’s version, indicates that Madonna, in this film, can be viewed as a contemporary application of that body of thought. Moreover, discussion on this topic highlights current and often troubling concerns for feminist film theory, in the face of postmodern formulations, surrounding concepts of subject-object polarity that have played a fundamental role in theorizing the Other.