This chapter introduces the main topic of the study: the importance of advertising and translation in defining culture and identity, and the way the two disciplines interrelate. The question of brands in literature and literature in advertising is cross-culturally examined, highlighting the dynamics of localization and translatability into other languages. Great Britain and the US have paved the way to the global advertising culture. Selected case studies based on brands and products are thematically compared (coffee, chocolate, Coca-Cola, hamburgers) in original texts and translations. The impacting factors and circumstances are analysed in terms of cultural translatability. There is a correlation between aspects of “translatability” and “advertisability,” a key factor determining the freedom of expression in a free market. Translatability broadly extends to intertextual and multimodal aspects, such as film adaptations and product placement. Most importantly, it sheds light on deletion, manipulation, and censorship. Items selected feature British lifestyles and literary icons (London, James Bond, and Willie Wonka) juxtaposed with the American iconography of advertising in literature and films (Texas, California, New York, Alabama, Mississippi, the West, etc.). It also contextualizes the use of brand names in literature, film adaptation, and product placement and features diachronic variation in translation and advertising in literature and films (e.g., Fascism in Italy) and Italian product placement in Hollywood. Translation and advertising studies have for a long time been denied academic status, but the integration of the two areas is a vital link to monitor and survey the dynamics of cross-cultural communication and globalization.