There are many reasons for taking an academic interest in both Nabokov's 1955 novel, Lolita, and its 1962 film adaptation by Kubrick. Not least of these is the interest per se of their work, in their quality (in both senses of the word) despite any controversy due to the theme chosen. Both works are growing in prestige. Their artists have a gift for provocation, but that alone is not enough for them to emerge as giants of literature and film-making. The point of interest here is the humorous nature of their work, and how that relates back to the nature of humour, and how all of this is relevant to translation studies, as illustrated in the examples presented. A useful measure for this venture is Adrian Lyne's own 1997 film version of Lolita, claiming as it does to be a more faithful rendering of the book than the 1962 one. Kubrick and Lyne both reflect much of Nabokov's novel, but only Kubrick's is (classified as) comedy. All other things being equal, mostly, this provides unique insight into the nature of humour (at least in comedy) and the benefits of translating it to be funny and, to fit the genre of comedy. We find that sex and taboo are alluded to by Kubrick in words and images, whereas Lyne is more visually explicit. The aim of this paper 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.