At the publication of Vladimir Nabokov's controversial novel "Lolita" (1958), the author insisted that a girl never appear on the cover. This discourse analysis of 185 "Lolita" book covers, most of which feature a girl, considers the genealogy of "Lolita" in relation to representation, myth, and tacit knowledge construction. How does the content and context of the narrative function to promote and propel erotic girl imagery and reiterate blameworthiness of the girl as seducer? Using visual discourse analysis (Rose, 2001) to analyze book cover representations, findings suggest cultural understandings of "Lolita" are connected to mythic signifiers and popular culture notions of girlhood gone bad. Also described and analyzed, a recent book cover contest that asks designers to create a "Lolita" book cover that does not use a girl. This study encourages art educators and their students to question how culture perpetuates myth, and more specifically, why.