The purpose of this study is to introduce William Day’s analysis of Wittgenstein’s criticism of Shakespeare as well as to offer a commentary on his analysis, thereby facilitating the understanding of Wittgenstein’s criticism. Wittgenstein left a series of short comments in his personal notes in his last years, which were about the discord of literary taste between him and Shakespeare, about his not-so-celebratory opinion about Shakespeare’s achievements and about his unhappiness with the glittering facade of Shakespeare’s universal fame of his days. Day relates Wittgenstein’s own alleged difficulties in understanding Shakespeare to the former’s philosophical concepts of “aspect-seeing” and “aspect-blindness,” and connects the characteristic ‘condition’ of Shakespeare’s literature leading to Wittgenstein’s uneasiness of understanding to the former’s “dream-like recollections of an indeterminate cause” diagnosed by Wittgenstein. Arguing that, in order to get to the hidden motive of Wittgenstein, it needs to examine the ways Shakespeare and Wittgenstein each respond to the “human threat of skepticism,” Day points out, following Stanley Cavell’s related line of discussion, that Shakespeare’s way consists in turning our relation to the world and to others “into matters of knowing,” and Wittgenstein’s way lies in affirming the thesis, while not negating the concluding thesis of skepticism, that our relation to the world as a whole, or to others in general, is not one of knowing in search of certainty. Day argues that the reason, while capturing the problem running through Shakespeare’s literature, Wittgenstein dislikes the latter’s wildly rendered tragic consequences lies in its “raw motives to skepticism,” its “language gone wild” in absence of “philosophical elaborations and filigrees.” This study further explicates this specialist, elliptical and a little abstruse analysis of Day’s for readers to understand, and not misunderstand, Wittgenstein’s enigmatic barbed remarks on Shakespeare.