1. The Prince, by Machiavelli: for exemplifying the strictly instrumental approach to politics, and reminding me that it's valuable because good policies are useless unless you have the power to enforce them.
2. Some Versions of Pastoral, by William Empson: for the notion that "life is essentially inadequate to the human spirit, yet a good life must avoid saying so" -- as Empson said elsewhere, that "life involves maintaining oneself between contradictions that can't be solved by analysis" -- which is at the heart of Empson's sense of the importance of literature. There's an internal paradox in this, I suppose, as Empson also declared elsewhere that "Critics, as barking dogs, are of two sorts: those who merely relieve themselves against the flower of beauty, and those, less continent, who afterwards scratch it up. I must, I confess, aspire to the second of these classes." The Pastoral book is the most important because it quite directly addresses the question of propaganda from a literary perspective, and once -- like me -- you've decided that there aren't objective moral truths, the study of propaganda becomes terribly important.
3. Collected Essays by George Orwell: especially the ones about Lear and Gandhi, which raise an important issue:
The essence of being human is that one does not seek perfection, that one is sometimes willing to commit sins for the sake of loyalty, that one does not push asceticism to the point where it makes friendly intercourse impossible, and that one is prepared in the end to be defeated and broken up by life, which is the inevitable price of fastening one's love upon other human individuals. No doubt alcohol, tobacco, and so forth, are things that a saint must avoid, but sainthood is also a thing that human beings must avoid.This is a dangerous idea to take seriously -- it seems clear that there are at least some ways in which human beings leave room for unambiguous improvement -- but it identifies something that I've always considered a bit whiffy about the saints.
4-5. The Dyer's Hand and Collected Poems by W.H. Auden: for a more-or-less worked out attempt, though ultimately a flawed one, to create a sensible contemporary ethics. Auden's essay on "making, knowing, and judging" is a classic; so are a lot of the famous -- and facially silly -- distinctions between Europe and America in "The American Scene," which periodically give way to passages like this:
As the issue between virtue first and liberty first becomes clear, so does the realization that the cost to any society that accepts the latter is extremely high, and to some may seem prohibitive. ... But if the principle is accepted, it means accepting this: it means accepting a State that, in comparison to its Roman rival, is dangerously weak (though realizing that, since people will never cease trying to interfere with the liberties of others in pursuing their own, the State can never wither away. Tyranny today, anarchy tomorrow is a Neo-Roman daydream); it means accepting a “Society,” in the collective inclusive sense, that is as neutral to values (liberty is not a value but the ground of value) as the “nature” of physics; it means accepting an educational system in which, in spite of the fact that authority is essential to the growth of the individual who is lost without it, the responsibility for recognizing authority is laid on the pupil; it means accepting the impossibility of any “official” or “public” art; and, for the individual, it means accepting the lot of the Wandering Jew, i.e. the loneliness and anxiety of having to choose himself, his faith, his vocation, his tastes.And of course "In Praise of Limestone"
6. The Penguin Book of Everyday Verse, ed. David Wright: for a good introduction to the folk poetry of the Middle Ages, the Renaissance, and the early 19th cent., which leaves one at least somewhat conscious of the limits of "progress" and of the extent to which human life is a zero-sum game that cannot be raised very far above the level of farce, regardless of how much technological progress one makes.
7. In search of lost time by Marcel Proust: for its brave attempt to argue that life is worth living because the pleasant recollections that pile up over time are enough to justify the drab interstices between them. (This offers an indirect resolution to the "lifespan dilemma" -- if your average utility per moment is proportional to how long you've lived before that moment, then average and total utility are the same thing and a long life is worthwhile on either count. I'm not, btw, convinced that this is the case, but Proust's way of reconstructing a life from its sensations makes it seem at least possible.)
8. Ulysses by James Joyce: for refuting the solipsists by example. You can stub your toe on Bloom.
9. The Canterbury Tales: for offering a reasonably complete portrait of what might be considered a harmonious "beehive" society; for making it seem a beautiful whole despite the lack of adequate plumbing; and for, in a somewhat limited sense, his defense of human existence as at least pleasantly vigorous if not dignified.
10. A Tale of a Tub, Gulliver, etc., by Jonathan Swift: for offering, through his unremitting and entertaining misanthropy, a credible case for the prosecution (contra Chaucer, that is).