This chapter is dedicated to a designated moment of philosophical discontent: a discursive instance in which three philosophers—Noël Carroll, Carol Brownson, and Jack C. Wolf—confronted head-on the monumental “hard problem” of the meaning of Documentary by deploying analytical tools that had thus far been unexploited in making sense of the luring nature of documentariness. By 1983, questions concerning the meaning of documentary films—as it became evident that they bear and induce cultural, social, political, artistic, and intellectual curiosity—became a significant challenge for the emerging academic debate within a new generation of thinkers who were about to shape the discourse for the coming decades. The chapter studies the four-step conversation among the philosophers, beginning with Carroll’s “From Real to Reel” and moving on to Brownstein’s reply entitled “Objectivity and Nonfiction.” Her response prompted, in turn, a reply from Jack C. Wolf, addressing both her and Carroll. His reply was entitled “Carroll’s ‘From Real to Reel’” (1983). Wolf’s reply led to Carroll’s concluding reply, this time to Brownson and Wolf, entitled “Reply to Carol Brownson and Jack C. Wolf” (1983).