To re-examine the subject of ＂history,＂ my research attempts to deal with the possibility of re-subjectifying histories via the facets of dramaturgy and theatrical arts. My analysis will focus on the case study of ＂Troilus and Cressida＂. ＂Troilus and Cressida＂ is Shakespeare's reworking of the historical, mythological, and epic poetic paradigm concerning the initiation of a notorious, iconic war and the futile strife between the Trojans and the Greeks due to a certain feminine token (Helen at first and then Cressida next), thereby revealing the playwright's overt endeavor for reshaping (＂ridiculing＂) a literary classic and assuming (＂violating＂) history. By so doing, the writing in ＂Troilus and Cressida＂ aims not only at paradigm shift in a sense, but also at intertextuality, by positioning itself as a self-referential meta-text that welcomes multifarious readings, and generates ＂polyphonic＂ texts. ＂Troilus and Cressida＂ is infamous as a Shakespearean problem play. As a problem play, ＂Troilus and Cressida＂ is characterized by complex structures, cross/ambiguous genres, and moral quandaries; by a blur and a de-canonization of the orthodox dramatic categorizations of tragedy, comedy, and chronicle/history plays. In the first sections, I will quickly go over a number of compelling reasons that identify ＂Troilus and Cressida＂ as an indefinable problem play. My explanation of the play as ＂problematized＂ shall also contribute to re-subjectifying (and representation of) histories. My discussion will consist of the following four aspects: 1) responses of audiences, critics of the stage production, and the trajectory of scholarship; 2) the reflection of dark, satirical, even pathologically absurdist social controversies, together with perplexing, melancholic, disquieting public issues as the play's ＂thesis.＂ My examination will also contain: 3) intrinsic ＂structural problems＂ as dramatic/artistic flaws; 4) ＂problematic structure＂ as a self-reflexive critical stance, which ＂takes a step back＂ so as to allow room for dialectical dynamics. Such problematic structure, essential to Shakespearean problem plays, like ＂Troilus and Cressida＂, thus opens up uncanny spaces and fissures for (post) modern theories to interrupt, intervene and ＂negotiate＂; to violate, ＂deconstruct＂ and remold. On the one hand, heroism, idolization of masculinity, and vanity of militarism inevitably still overwhelm and outshine in ＂Troilus and Cressida＂ (dramatized in, for example, Priam, and above all, Agamemnon's pale, tedious, empty, monologuous metanarratives). On the other hand, I see clearly Shakespeare's intention of the simultaneous juxtaposition of ＂de-machismo,＂ ＂iconoclast,＂ and ＂nihilism＂ through encouraging, igniting, and fermenting the hilarious dialogism of minor narratives in the text (manifested in, for example, Hector, Achilles, Ulysses, Thersites, Troilus, Calchas, Pandarus, and Ajax's anti-heroic pursuits, individual desires, and trivial causes). This is what I call a disenchantment of multiple/micro perspectives on histories that are absorbed and embroiled in macro History and clean-cut, grand narratives. On the matter of research methodology, in addition to close reading of the play, I will employ ideas and texts of Nietzsche, Existentialism, and Post-Structuralism (in particular J. F. Lyotard's concepts of metanarratives and little narratives) that validate the theoretical foundation of this paper.