This study highlights the problems of translating Shakespeare's food and drink-related insults (henceforth FDRIs) in (Henry IV, Parts I&II) into Arabic. It adopts (Vinay & Darbelnet's:1950s) model, namely (Direct& Oblique) to highlight the applicability of the different methods and procedures made by the two selected translators (Mashati:1990 & Habeeb:1905) .The present study tries to answer the following questions:(i) To what extent the FDRIs in Henry IV might pose a translational problem for the selected translators to find suitable cultural equivalents for them? (ii) Why do the translators, in many cases, resort to a literal procedure which is almost not workable with such expressions. (iii)What is the main reason behind the high percentage of inappropriateness in translating FDRIs from English into Arabic? As for the main conclusions that the study has come up with, we can sum up them in the following points.(i) Most of the FDRIs are culturally bound expressions with cultural peculiarities making them very hard to be deciphered and translated even by experienced translators.(ii) Most of the FDRIs used by Shakespeare in his tragedy Henry IV, are very old and were his own inventions, a fact that makes them very difficult not only for the non-native speakers of English as the case with our translators (Mashati &Habeeb) but also for the native speakers. (iii) Finally, one can say that all the wrong and funny renditions were due to the wrong adopted procedures by (Mashati &Habeeb) , while the other successful renderings were as a result of their well-selected procedures  that consider the cultural difference between the two languages.