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Bring on the tough stuff - there’s not just one right answer.
What is a totalitarian regime? How does such a regime attain, maintain, and increase power? What is its main concern? How does it compare with other political structures? Democracy, for example?
What role does technology play in this book? In what ways does the Party employ technology? In what ways does technology make the overall themes of this book possible?
Which is worse: mind control or physical control? In what sense are they one and the same?
Think about Newspeak. Does language shape thought? Action? Is language necessary for either thought or action? Without language, does reality exist? Does perception?
What role does Big Brother or Emmanuel Goldstein have in the book? Do they exist? Must they exist? How do they affect Winston? Is Winston’s obsession with Big Brother really the same as his obsession with Goldstein?
So someone somewhere said that one who controls the past also control the present, and therefore, the future. True, or not so true? What role does memory play in an accurate account of history? Can history ever be objective, after all?
Winston says at one point that he "understands the how, but not the why" behind the Party. This is before he is apprehended, tortured, and converted. At any point during this marathon of unfortunate events does he get to know the why? Do we, the readers, get to know the why? If so, what is it?
What is the effect of having the story broken into three, distinct parts?
Take a look at the three Ingsoc mantras: war is peace, freedom is slavery, and ignorance is strength. The first two are natural opposites (at least last time we checked). But what about that last one? Orwell seems to be saying that ignorance is the opposite of strength. Why not say "weakness is strength?" Does 1984 make a successful argument for ignorance being the same thing as weakness?