Due to the nature of live theatre, drama has persistently been used to explore postmodernist concerns throughout the years, since the inevitable boundary blurring in theatrical performances makes drama the perfect medium to examine such concerns. According to Brian McHale, “insofar as postmodernist fiction foregrounds ontological themes and ontological structure [...] it is always about death,” drawing a tight link between postmodernism, death, and drama. The postmodern preoccupation with death, then, becomes an interesting phenomenon to investigate when it is examined through drama performances, especially when death is portrayed in ways besides the conventional. Using three plays from three distinct periods, Molière’s The Hypochondriac, Luigi Pirandello’s Six Characters in Search of an Author and Tom Stoppard’s Rosencrantz and Guildenstern Are Dead, this paper will attempt to show how these plays are, first and foremost, concerned with postmodernist themes, especially in the case of Molière, a French Neo-Classical play that is, on first look, anti-postmodern. After that, this paper will also analyze the ways death is portrayed in each play, showing how the staging of death is used to exemplify the breaking down of ontological boundaries. Keeping in mind McHale’s assertion that [p]ostmodernist writing enables us to experiment with imagining our own deaths, to rehearse our own deaths,” this paper proposes that, although theatre is used in attempts to experiment with the notion of death, it still potentially fails to capture death successfully.