Batman is one of the major superheroes since 1960s, having its commercial peak with Christopher Nolan’s film trilogy in the 2000s, as well as an artistic renaissance with the psychological spinoff drama Joker. The current chapter examines Batman from a personality psychological point of view, as well as with regard to the character’s persona. This perspective is supported by a transformative understanding of Batman as a masked persona. Other masked characters in the Batman universe such as Joker, Two-Face, Catwoman, and Bane are also highlighted. The analysis suggests that Batman shares features of both a conventional hero, an anti-hero and villain, and therefore his mask and costume might be seen as floating signifiers. The complexities of supporting characters show a similar pattern in the case of Selina Kyle, A.K.A. Catwoman, whereas Two-Face, Bane, and Joker manifest more unambiguous villain elements.