This paper will deal with Nabokov’s screenplay of Lolita as well as two cinematic texts—Kubrick’s and Lyne’s versions of Lolita—in the context of translation. Alfred Appel effectively demonstrated in Nabokov’s Dark Cinema that cinematographic allusions and references are omnipresent in Nabokov’s fiction. Lolita, however, is a special case due to Nabokov’s involvement in 1959–1960 in the “cinemazing”,to use his own term, of his famous novel. The result of his collaboration with Kubrick was the acclaimed motion picture Lolita. Nabokov was first to discuss this film adaptation in terms of translation: in the foreword to the script, Nabokov, grappling with the modifications and omissions of entire scenes in Kubrick’s film, speaks of the film in terms of translation’s fidelity and freedom in regard to the original and compares it to Robert Lowell’s “unfaithful” translations from Rimbaud and Pasternak. The paper will discuss what happens to the text of the novel as it undergoes a Heideggerian “Umschreibung” of sorts—the passage from the literal to the figurative—and the rhetorical implications that open up in the process. Incorporation of some of the previously unpublished materials in the possession of the Berg Collection, including three different versions of the script Nabokov wrote for Kubrick, enriched my attempt to unravel the “mechanics” of Nabokov’s transformational strategies. Finally, I would like to examine the “Umdeutung,” Kubrick’s and Lyne’s reinterpretations of Nabokov’s screenplay and novel. This form of translation, according to Heidegger, constitutes the transition to a different domain of experience; the difference in this case is not rhetorical but hermeneutic.