The financial crisis and economic recession that hit Europe and the U.S. after 2007 has made financial affairs a topic of considerable interest to writers and filmmakers alike. This paper is a first step toward a comparative analysis of a number of novels and films that have addressed the theme of finance in Italy, Great Britain, and the U.S, obtaining high cultural visibility. The provisionary corpus of this study includes: Resistere non serve a niente, by Walter Siti; This Bleeding City, by Alex Preston; The Wolf of Wall Street, by Martin Scorsese; and The Big Short, by Adam McKay. Through a close reading of the texts, the paper highlights their respective discursive strategies, and assesses the representation of finance that each of them might generate in the mind of a lay reader. The ideas that emerge from the texts are then compared and contrasted with those of professional debates, from newspaper columns to economic blogs and journals. Aside from the predictable choices of characterizing stockbrokers as ferine and arrogant people, and employing redundant—and sometimes cacophonous—financial technicalities in which readers/viewers are likely to get lost, all four texts show an earnest intention to raise awareness about the concrete shortcomings of modern finance.  The final outcomes, however, greatly differ from each other. In short, Preston’s This Bleeding City and McKay’s The Big Short give intelligible clues on the workings of contemporary financial markets, Siti’s Resistere non serve a niente only echoes a series of subjects that already populate public discourse without adding new insights, and Scorsese’s The Wolf of Wall Street presents a caricature of finance verging on the farcical.