Abstract This thesis attempts to contribute to both intermedial studies and F. Scott Fitzgerald scholarship by studying the text-illustration interplay in two versions of “The Rich Boy”. Intermediality, which pays close attention to media interactions, is a natural method to explore the word-image relations in these texts: the first version, published in Red Book Magazine in 1926, and an illustrated Spanish translation from 2012.             Lars Elleström’s definition of media as a combination of modes and modalities, plays a central role in the analysis, where I study how these interact in each text: For instance, in terms of the material and sensorial modalities, both illustrators try to simulate depth and convey the senses in a flat interface. In terms of the spatiotemporal modality, the anachronies in the time placement of Gruger’s images intensify the nostalgic mood in the text, while Ágreda’s adherence to the text’s time relays a certain autonomy. Both their treatments of space are often symbolic; thus, regarding the semiotic modality, the images are symbolic besides iconic. Each text is colored by the reading of the illustrator, who is also a reader and interpreter.             The theoretical framework also comprises of an approach to nostalgia: While Fitzgerald’s story is nostalgic per se, the illustrators display variations of nostalgia: Gruger’s work mirrors and enhances the nostalgic mood of the text, and while to a certain extent, Ágreda’s also does this, his nostalgia is most manifest in how he attempts to recreate a particular picture of the Jazz Age.