Tom Stoppard’s theater is particularly concerned with the evasive and illusory nature of truth. Drawing upon the prominent tenets of chaos theory and pertinent postmodern concepts, the present research aims to offer a new reading of three of Stoppard’s major works, namely, Indian Ink, Rosencrantz and Guildenstern Are Dead, and Arcadia, suggesting that in their concern with the very concept of truth and reality, their celebration of the chaotic and the orderly as inseparable and integral components of ontological and epistemological modes of being and knowing, their endless cycles and repetitions and their emphasis on the postmodern uncertainty, these plays are open systems which allow an incessant flow of information, thus depicting the realities of the contemporary time. As such, through implementing such concepts as intertextuality, multiple concepts of language, noise and information, historical representation, deterministic chaos and unfixity of truth, Stoppard’s defamiliarization of the concept of the truth, demonstration of the suppressed possibilities, and revealing the (in)accuracy of historical documents are foregrounded. It is argued that through an informed projection of the fluid concept of reality and truth, Stoppard reflects the fallacy of belief in order, fixity and determinacy.