There are numerous reasons for taking an academic interest in both Nabokov's (1955/2000) novel, Lolita, and Kubrick's (1962) film adaptation. Not least of these is their work per se, its quality (in both senses of the word) despite any controversy due to the theme chosen. Both works are growing in prestige. These artists have a knack for provocation, wittingly or unwittingly is beside the point, but provocation alone is surely not enough for them to emerge as giants of literature and filmmaking. The point of interest for the present study is the humorous nature of their work, and how that relates back to the nature of humor, and how all of this is relevant to translation studies, as illustrated in a handful of examples. A useful measure for this quest is Adrian Lyne's (1997) film, claiming as it does to be a more faithful rendering of the book than Kubrick's. Kubrick and Lyne coincide in much of Nabokov's novel, but only Kubrick's is (classified as) comedy. All other things being equal, by and large, this provides insight into the nature of humor (in comedy) and the benefits of translating it comically, to fit the genre of comedy, and as an element of other texts. We also find that sex and taboo are alluded to by Kubrick in words and images, whereas Lyne is more visually explicit. The aim is to show a case study of how censorship, taboo and ideological misconceptions of an author's work can affect its perception by the public, so that it becomes unclear whether popular images of Lolita as a fictional character are a cause or a consequence of certain translations and new film versions such as Adrian Lyne's.