Books (there are many dozens)
Varied Types
What’s Wrong With the World
The Crimes of England (1916)
Fancies versus Fads (1923)
Heretics
I consider this the greatest book of essays ever written. And probably will until another of Chesterton’s books seems greater.
Orthodoxy
William Blake
The Everlasting Man (1925)

Autobiography
Robert Louis Stevenson (at least 2 different books by that title)
George Bernard Shaw
St. Thomas Aquinas

Quotes

++++His unique, his capital genius for illustration by parallel, by example, is his peculiar mark…. No one whatsoever that I can recall in the whole course of English letters had his amazing—I would almost say superhuman—capacity for parallelism.
++++Now parallelism is a gift or method of vast effect in the conveyance of truth.
++++Parallelism consists in the illustration of some unperceived truth by its exact consonance with the reflection of a truth already known and perceived….
++++Thus if some ass propounds that a difference of application destroys the validity of a doctrine, or that particulars are the enemies of universals, Chesterton will answer: “It is as though you were to say that I cannot be an Englishman because I am a Londoner.” … Always, in whatever manner he launched the parallelism, he produced the shock of illumination. He taught.
++++He made men see what they had not seen before. He made them know. He was an architect of certitude, whenever he practised this art in which he excelled.
++++The example of the parable in Holy Writ will at once occur to the reader. It is of the same origin and of similar value. The “parable” of the Gospels differs only from pure parallelism in the artifice of introducing a story in order to capture the reader’s mind. But in essence a parable is the same thing as a parallelism.
++++Let us remark in conclusion that parallelism is of particular value in a society such as ours which has lost the habit of thinking. It illustrates and thereby fixes a truth or experience as a picture fixes a face or landscape in the mind. – Belloc, quoted in Bloom’s GKC

++++Language is not thought, and thought is not reality, any more than figures in a ledger are money, or money is human wealth. Yet one must always use language and thought, as the book-keeper must always use figures and coins. One can never, in short, escape parallelism; and we never speak but in parables.
++++“I doubt whether any truth can be told except in parable,” Chesterton makes one of his characters say; and the proposition is accompanied by its Chestertonian corollary: “I doubt whether any of our actions is really anything but an allegory.” That these observations were self-evident to him in the light of his metaphysical intuition of being may be guessed from the central lines of the poem Ubi Ecclesia:
++++++ Where things are not what they seem,
++++++ But what they mean.
++++– Hugh Kenner, quoted in Bloom’s GKC

False religion…is always trying to express concrete facts as abstract; it calls sex affinity; it calls wine alcohol; it calls brute starvation the economic problem. The test of true religion is that its energy drives exactly the other way; it is always trying to make men feel truths as facts; always trying to make abstract things as plain and solid as concrete things; always trying to make men, not merely admit the truth, but see, smell, handle, hear, and devour the truth. – GKC, Alarms and Discursions, p59

If you say, “The social utility of the indeterminate sentence is recognized by all criminologists as a part of our sociological evolution towards a more humane and scientific view of punishment,” you can go on talking like that for hours with hardly a movement of the grey matter inside your skull. But if you say, “I wish Jones to go to gaol and Brown to say when Jones shall come out,” you will discover, with a thrill of horror, that you are obliged to think. The long words are not the hard words, it is the short words that are hard. There is much more metaphysical subtlety in the word “damn” than in the word “degeneration.” – GKC, Orthodoxy, p229

If all things are always the same, it is because all things are always heroic. If all things are always the same, it is because they are always new. To each man one soul only is given; to each soul only is given a little power—the power at some moments to outgrow and swallow up the stars. If age after age that power comes upon men, whatever gives it to them is great…. We who do the old things are fed by nature with a perpetual infancy. No man who is in love thinks that anyone has been in love before. No woman who has a child thinks that there have been such things as children…. Yes, oh, dark voice, the world is always the same, for it is always unexpected. …
++++Men live, as I say, rejoicing from age to age in something fresher than progress—in the fact that with every baby a new sun and a new moon are made. If our ancient humanity were a single man, it might perhaps be that he would break down under the memory of so many loyalties, under the burden of so many diverse heroisms, under the load and terror of all the goodness of men. But it has pleased God so to isolate the individual human soul that it can only learn of all other souls by hearsay, and to each one goodness and happiness come with the youth and violence of lightning, as momentary and as pure. And the doom of failure that lies on all human systems does not in fact affect them any more than the worms of an inevitable grave affect a children’s game in the meadow. Notting Hill has fallen; Notting Hill has died. But that is not the tremendous issue. Notting Hill has lived. – GKC, The Napoleon of Notting Hill, V,iii pp193-200

Further reading

Two renowned books I want to read but haven’t managed to get a hold of yet:
Paradox in Chesterton – Hugh Kenner
Chesterton: Man and Mask – Garry Wills, 1961

“Etienne Gilson…[w]hen St. Thomas appeared…said to a friend of mine ‘Chesterton makes one despair. I have been studying St. Thomas all my life and I could never have written such a book.’ After Gilbert’s death, asked to give an appreciation, he returned to the same topic—‘I consider it as being without possible comparison the best book ever written on St. Thomas. Nothing short of genius can account for such an achievement. Everybody will no doubt admit that it is a “clever” book, but the few readers who have spent twenty or thirty years in studying St. Thomas Aquinas, and who, perhaps, have themselves published two or three volumes on the subject, cannot fail to perceive that the so-called “wit” of Chesterton has put their scholarship to shame. He has guessed all that which they had tried to demonstrate, and he has said all that which they were more or less clumsily attempting to express in academic formulas. Chesterton was one of the deepest thinkers who ever existed; he was deep because he was right; and he could not help being right; but he could not either help being modest and charitable, so he left it to those who could understand him to know that he was right, and deep; to the others, he apologized for being right, and he made up for being deep by being witty. That is all they can see of him.’” – Maisie Ward, Gilbert Keith Chesterton, 1943, p619–20