The present paper compares and discusses different illustrations of Roald Dahl’s James and the Giant Peach through a translational prism. For this purpose, two different editions of this story (Dahl 1991; Dahl 1995) illustrated by two different artists (Michael Simeon and James Blake respectively) have been analyzed. After selecting several pictures depicting the same situations, the article intends to explain illustrators’ decisions using theoretical aspects of translation. In this vein, the paper seeks to identify different translation procedures that stem from the analysis of the relationship between pictures and words. Such analysis is aimed at providing solid grounds to subsequently categorize the pictures according to the information they include and transmit, and their interrelation with the text. In order to achieve this aim, a comprehensive study of the chosen illustrations is conducted, focusing on five specific translation procedures: literal translation, omission, explicitation, paraphrase, and transcreation. Thus, the paper seeks to identify the different translation strategies implicit in the decisions taken by the illustrators, and their impact on their drawings. The aforementioned data is eventually used as evidence to determine the type of interaction established between text and illustration, and the implications such interactions may have on the reader.