People often ask me to recommend books to them; I never know what to say in reply. This is obviously a strange quirk of mine, because I see others recommending books all the time, fully and freely. Why is the task such a puzzler for me?
I think it's because, as I see things, there are very few books that anyone and everyone should read. Maybe there aren't any. But any books that would be on such a list — the Iliad or Hamlet or Dante's Divine Comedy — are already universally known. So presumably people who ask for recommendations are looking for less obvious additions to their reading lists.
But in that case, I really don't have a reliable way of knowing — except perhaps in the case of good friends — whether a given person would enjoy and benefit from a given book. Readers (people) are so different from one another: they have such widely varying experiences, educational backgrounds, aesthetic preferences, and personal needs. I just don't have any confidence that a book I happen to like, or have learned from, would be well-suited for someone else. So in the past when I have provided recommendations on request, I have felt that I was just pulling marbles out of a black bag, that my choices were pretty much completely random and that on another day I might have mentioned completely different books.
The result is that now, when I'm asked for recommendations of books to read, I end up just thinking about it for an unconscionable length of time, and not really coming up with anything. Weird, huh? Nevertheless, that's the situation.
And besides, I am a big, big believer in reading at whim.
Nevertheless, as a token offering, I can direct you to a blog post I wrote about the books that were most important to me at different stages of my life. I have also tried to make a case that Rebecca West's Black Lamb and Grey Falcon is one of the greatest books of the twentieth century — perhaps the very greatest. Surely nearly everyone should read more Auden. The most profound guide to Christian sanctification I know is Dante's Purgatorio. Two novels I would love more people to read are Anita Desai's Clear Light of Day and George Garrett's The Succession. Few works of history are more profound than Charles Norris Cochrane's Christianity and Classical Culture, which was a particular favorite of Auden's — he read it "many times," he said. If I could get my fellow Christians to read only one recent book it would be Lesslie Newbigin's The Gospel in a Pluralist Society — a lifetime of missional wisdom condensed into one book.
I learned a great deal about writing biography from studying the two major biographies produced by Walter Jackson Bate: Samuel Johnson and John Keats. If I had had time to go back and re-read and study those two books before writing my biography of C. S. Lewis, its quality would have been much improved, I am sure. (Maybe someday a second, revised, expanded, and improved edition. . . .)
I may add things to this list later.