This article aims to explore the extension and evolution of Shakespeare’s The Merchant of Venice through Michael Radford’s 2004 cinematic adaptation. By investigating the concept of adaptation and the significance of intertextuality, Shakespeare’s source text is considered alongside Radford’s twenty-first century recreation to reimagine and redefine the construction of Shylock as both a comic and tragic device utilized across film and play. Issues of racial and religious prejudices alongside anti-Semitic views were particularly prominent in Elizabethan England and, by concentrating on recontextualisation, this article looks to expose Shakespeare’s characterization as a reflective commentary concerning societal discriminations at the time of the play’s performance. By focusing primarily on Shakespeare’s Jewish Usurer, Radford is able to reconstruct and reestablish the dramatic devices and characters within the cinematic version, metaphorically converting Shylock from comic villain to tragic victim. Finally, it argues that this dynamic shift inevitably metamorphoses Shylock from a spectator’s perspective and provides Michael Radford with an opportunity to offer a social commentary on social inequality in the twenty-first century.