Since it was first introduced by Jacques Derrida in the late 1960s, deconstruction, as a method of reading, has been applied to literary texts by critics to reveal the hidden messages of texts and provide opportunities to rethink textual and cultural norms and conventions. While the western tradition has always prioritized tragedy over comedy due to its elegance and graveness, this research tends to focus on comedy as an entity in itself. Tragedy, especially in the Shakespearean sense of the word, has been considered by critics as a “construction” that is well-wrought and perfect in nature. Comedy, on the other hand, is notable for laughing at the laughable and mocking the unfit. Put differently, there has always been a latent, freewheeling “deconstruction” within comedy, especially the Shakespearean. There is, thus, an attempt here to prove, on the one hand, how comedy can be put forth not as an inferior genre but as a supplement to tragedy and, on the other, how comedy moves toward deconstruction and how it tends to subvert or deconstruct the constructions. Investigating a selection of Shakespeare’s comedies including As You Like It, The Merchant of Venice, and Twelfth Night, this study compares and contrasts Shakespearean comedy in light of some Derridean concepts. Along with it, Shakespearean ideas and concepts which are interconnected with those of Derrida are introduced and are buttressed through some meticulously chosen excerpts. Bearing in mind that Derrida is in a habit of deconstructing the so-called established creeds, Shakespeare’s texts are exposed to a deconstructive reading to examine how deceptively simple ideas are dealt with in his selected comedies. Also, as numerous enigmas have for years revolved around the personality of William Shakespeare, this study also aims to take up certain critical idioms of the Derridean canon, elaborate on them and then relate them to the selected plays from the Shakespearean oeuvre in order to disclose some personal aspects of Shakespeare’s personality as a historical figure.