A greater awareness of how Pinter’s early experiences as a Shakespearean actor have influenced his playwriting gives us considerable insight into Pinter’s playwriting strategies. Four different approaches are used to examine multifarious Shakespearean resonances in Pinter’s plays. Pinter’s portrayal of Iago on stage may have been a contributing influence to some of the language games in Pinter’s plays. Metadramatic attributes shared by Shakespeare and his character Iago are extended to Pinter and his character Robert in Betrayal.A Jungian reading of Hamlet is juxtaposed with Pinter’s political plays, Ashes to Ashes and One for the Road, to examine how manipulators in these plays attempt to obliterate individual identities and reduce individuals to pawns by foisting national and paternal identities onto characters. Hamlet’s and Rebecca’s resistance to such threats are examined in terms of their endeavours to unite opposites in their quests for individuation. This study sheds light on the strong antithetical structures and open-endedness in Shakespeare’s and Pinter’s plays.