Vladimir Nabokov’s Lolita and Pale Fire are exemplary works of art that continue to push the boundaries of aesthetic and ethical literary theory. Critics and theorists alike once strove to categorize these tenets so central to Nabokov’s work, but in current reviews many have chosen to defer a deterministic analysis of the novel’s themes and instead relegate the philosophical and artistic value of his texts to the realm of “potustoronnost” (“otherworld”). This paper argues that the artistic puzzle that motivates such a critical assessment is in fact more complexly related to Nabokov’s strong opinions about art, aesthetics, and ethics, and ignoring a finer analysis of these themes renders a general term such as “otherworld” unsatisfactory. My research explores two principle motifs—reality and imagination—in an attempt to join Nabokov’s artistic mechanisms with his well-established aesthetic and ethical axioms. Additionally, I invoke the preceding work of Gustauve Flaubert, Madame Bovary, in order to demonstrate how Nabokov has, almost a century later, complemented Flaubert’s negative representation of art’s integration into his characters’ average realities (via a literary critique of interested aesthetics) with a positive, humanistic perspective that invokes moral sentiment. This essay strives to show how beauty and morality connect reality and imagination to aesthetics and ethics; and ultimately, how these interrelationships provide a dimensionality to art that invites the thoughtful reader to an elevated state of “aesthetic bliss.” I offer a refreshing perspective on Nabokov’s artistic priority of attaining “aesthetic bliss” that synthesizes and expands upon the current dialogue.