This chapter traces the intertextual genealogy of adapted versions of Patricia Highsmith’s The Talented Mr. Ripley Novel by Patricia Highsmith with a focus on the most recent adaptationadaptation: Steven ZaillianZaillian, StevenZaillian, Steven’s Ripley. TomRipley, Tom Ripley is a protean character whose amoralityamorality and sexualsexuality blanknessblankness provide successive generations of adapters with an opportunity to remodel him for their times. However, it can prove difficult for audiences to connect with such blank characters because audiences are tutored by more conventional cultural products to take pleasure in identifying with protagonists. This means ZaillianZaillian, Steven, who has expressed a desire to be faithful to HighsmithHighsmith, Patricia’s original conception, faces the difficult task of translating his complex opacity to the screen while eliciting audience engagement with him. In this context, the chapter introduces Eric LeakeLeake, Eric’s concept of “difficult empathyempathy, difficult,” by means of which the spectator is encouraged to align with characters who breach the social contract, such as antiheroesantiheroes (Leake, 2014, 2024). It also asserts that the governing aesthetic of Ripley is forgeryforgery, which extends not only to Ripley’sRipley, Tom own impostureimposture, but also to the act of adaptation itself. The series engages in postmodernpostmodernism “complicitous critiquecomplicitous critique” of late capitalismcapitalism and also reflects post-postmodernpostmodernism and metamodernmetamodernism sensibilities (Hutcheon, 2002 p. 9).