This paper examines how men and women have been conventionally portrayed in gender stereotypes in various genres among different cultures through centuries in world literature, with reference to the classical Shakespearean play Macbeth (1606) by the British playwright William Shakespeare, the Hollywood road movie Thelma and Louise (1991) directed by Ridley Scott and A Doll’s House (1879) written by the Norwegian dramatist Henrik Ibsen. The research will explore the common themes embodied by the notion of gender almost in all literature work in the world which include patriarchy and order, masculinity and femininity, fabrication of identities, and binary opposition with the close textual analysis of the process of self-discovery and empowerment by the female protagonists, Lady Macbeth in Macbeth, Thelma and Louise in Thelma and Louise and Nora in A Doll’s House through the eyes of the male authors, namely playwrights and film director. By comparing the fates of aforementioned female protagonists in the three endings, the actual autonomy that women can take the lead in their life or act outside the normalized gender binaries is further studied. With the analysis of the literary devices and the depiction of the female characters’ psychological change with the visualization of symbols and attires in the texts, the relationship between form and content is also investigated. There is also the discourse analysis on the use of gendered language through soliloquies and dialogues, implication of gender roles in society and culture and the consequences of these females in transcending the gendered roles.