This chapter aims to examine the representation of Prince Charming from fairy tales to Disney products over the years. The depiction of female characters in Disney films has undergone a major shift over the years: since the 1990s, animated films have—at least apparently—generated a new strand in which female protagonists have been able to find new spaces of action and existence compared to the fairy-tale canon. This new conception of princesses, and of female characters in general, has been the subject of numerous international studies that have emphasised the need for a change with respect to past works, while at the same time highlighting some persistent critical points in the gendered representations proposed by Disney. However, less attention has been paid to masculine portrayals. Princes and male characters have undergone a transformation that has yet to fully deconstruct the canon of masculinity and offer new identity models to young viewers. Starting from the characterisation of Prince Charming in fairy tales, the chapter will analyse some case studies in order to outline and historicise some of the transformations that have affected the concept of masculinity in Disney works. In this way, Prince Charming’s perspective will be taken to point out some sexist elements in the construction of the character, who is often pigeonholed into toxic and harmful masculinities or used as a mere resolver of the narrative, rather than exploring his characteristics in depth and opening them up to new forms of identity. The chapter will draw on Gender Studies, Fairy Tale Studies, and Film Studies to propose a comparative analysis between different works and to outline some recurring or changing trends within the Disney universe.