This essay provides an analysis of the literary development of the genre of detective fiction in accordance with the critical insights of Leonard Meyer. We see how the postmodern mystery evolved out of the earlier “locked room” and “hard-boiled” mystery formats. We then examine the critical offerings of Jeffrey Nealon and Leo Strauss for hypothesizing a new post-postmodern esoteric mystery form. Two examples are offered by Agatha Christie and Vladimir Nabokov. However, this essay’s conclusion results in the posing of paradoxical problems for just such a hypothetical social-satirical and hoax-like construct. Indeed, my own mind’s desire to depict the post-postmodern mind may lead to this essay becoming a kind of post-postmodern mystery hoax itself.