Hugh Hewitt asks apropos a Tom Wolfereview, for recommendations of books to read moe than once. Somehow he omits then entire field of Science Fiction, which has more re-readable books than you could shake a neutronium plated stick at.
So if you haven't read any Heinlein or Le Guin or Arthur C Clark or Andre Norton then the short answer is why not? but because these are well known I'm going to recommend two more modern authors. Once better known than the other.
The first and better known is Lois McMaster Bujold - in particular the Vorkosigan series which is strongly recommended from first to last and is chock full of juicy epigrams and thought provoking concepts such as:
Reputation is what other people know about you. Honor is what you know about yourself.
As for which one to read - just follow Alice's advice and start at the beginning with Shards of Honor or Cordelia's Honor, the omnibus book that contains both it and its sequel.
The second and less well known author is Michael Z Williamson. He has only published one SF book on his own so far so the choice is simple - Freehold - which I raved on this blog about a couple of months ago.
PS Many of the book links link to the Baen website which contains free downloadable books and parts of books and is almost as addictive as crack cocaine. I have no connection with Baen other than as addictconsumer.