Good question! I'd say Winston awakes muttering "Shakespeare" because of three reasons. First, Shakespeare is a representative of that old culture that the Thought Police are trying to stamp out. Second, his language is the complete opposite of Newspeak, making many things possible. Third and most specifically, there is a line in "Hamlet" that sums up the attitude of this new society: "Why then 'tis none to you; for there is nothing either good or
" This society claims they can rework the world by controlling what people think, as the "mad" Hamlet suggests.
Early in the novel, we learn that Winston has a recurring dream about being in a "Golden Country" complete with elms and a meandering footpath, a pasture, a stream and willow trees: a rural idyll. A dark-haired woman is part of the dream. In this particular version of the dream, she tears her clothes off with a disdainful gesture. Winston doesn't feel sexual desire, but does appreciate her casual defiance:
What overwhelmed him in that instant was admiration for the gesture with which she had thrown her clothes aside. With its grace and carelessness it seemed to annihilate a whole culture, a whole system of thought, as though Big Brother and the Party and the Thought Police could all be swept into nothingness by a single splendid movement of the arm. That too was a gesture belonging to the ancient time. Winston woke up with the word ‘Shakespeare’ on his lips.
Shakespeare definitely represents that richness of language and thought, in all its nuance and complexity, that the Party is out to destroy. Shakespeare is a symbol of the old world of complicated emotions and ideas that the government is obliterating. As Syme says (convincing Winston by this utterance that Syme will soon be vaporized):
The whole literature of the past will have been destroyed. Chaucer, Shakespeare, Milton, Byron—they’ll exist only in Newspeak versions, not merely changed into something different, but actually changed into something contradictory of what they used to be.
The self-assertion in the dream woman's gesture, a gesture lacking the fear, anger, vengefulness, and aggression that are the common emotions of Party members, is to Winston a speech act reminding him of the independence and self-assertion of Shakespeare's characters and Shakespeare's writing.