In an alternative discursive universe, the protagonist of this chapter, Donn Alan (Penny) Pennebaker (1923–2019), might have been acknowledged, as odd as it might sound, either as the foremost advocate of the eighteenth-century Prussian philosopher Immanuel Kant, or, conversely, as his least-effective spokesperson. Such an unorthodox evaluation of one of America’s most original, fecund, and consistently productive and hailed documentarians for over six decades (1953–2016) and beyond is seemingly brittle: first, because it relies solely on a peripheral anecdote written by Pennebaker in an introductory paragraph to his lengthy conversation with G.R. Levin in September 1970 at his office in New York City (published in 1971), and second, because contrary to expectations, there is nothing in Pennebaker’s outspokenness, the profilmic and narrative layers of his rich oeuvre, or the extensive scholarly research on his work to suggest that Kant played a pivotal role in establishing a significant evaluation of his contribution to the history of Documentary. I’m even willing to go so far as to admit that, prima facie, the contrary would seem more plausible, namely, that it matters not at all, surely for him. Yet the chapter’s analysis of his definition of Documentary begs to differ.