In my thesis, I will analyse the gender representations, especially the gender behaviour of the antagonists’ in five Disney princess animations, four of them were produced before 2010; Cinderella (1950), The Little Mermaid (1989), Pocahontas (1995), and Hercules (1997) and one of them were created in the 2010s; Frozen (2013). I will focus on the depiction of characters who have gender-bending attributes and the way that in the earlier films these characteristics were always associated with villainy, while in newer versions the roles of these figures became more diverse. In the following, I will examine how transgender traits are represented in Disney movies which have male antagonist, I will concentrate on Governor Ratcliffe in Pocahontas (1995) and Hades with his henchmen, Panic and Pain in Hercules (1997), then I will contrast them with their female counterparts. In this chapter, I am going to talk about Lady Tremaine and her daughters, Drizella and Anastasia in Cinderella (1950) and Ursula’s character in The Little Mermaid (1989). Furthermore, I will argue that in recent movies, Disney corrected their misconception by analysing the characters Hans, Olaf, and Elsa in Frozen (2013) and by comparing them to the earlier versions.