This paper examines the depiction of Jews, particularly the character of Shylock, in William Shakespeare's The Merchant of Venice in comparison with those of two adaptations: Arnold Wesker's play The Merchant and Michael Radford's film The Merchant of Venice. Shakespeare's original work has been the subject of much scholarly discussion, with some perceiving it as perpetuating negative stereotypes and others as offering a nuanced and complex view of the character. Wesker's adaptation reinterprets the portrayal of Jews to challenge the negative representation in Shakespeare's play, highlighting themes of love, family, and relationships. Radford's film, on the other hand, offers a more nuanced and dynamic portrayal of the Jewish community than we are used to seeing in representations on film, and sheds light on the impact of anti-Semitic prejudice. It focuses on highlighting the Jewish/Christian disagreement and the extent to which Jews are victimized in Shakespeare's play, using filmic techniques to create a powerful representation with a deeper understanding of justice, discrimination, and dehumanization. Both adaptations offer a more nuanced portrayal of the Jewish community and challenge negative stereotypes perpetuated by Shakespeare's original work.