A High School kid told me that ze wanted to read: Dr. Zhivago Essays by Joan Didion The Power Broker Umberto Ecco Swann's Way Ayn Rand War and Peace Pushkin Dead Souls (Gogol) Lolita Don Quixote Catch-22 Toni Morrison Joyce Carol Oates so that ze would be smarter (ze is currently in the middle of Crime and Punishment and then moving on to War & Peace. I gather the list came from zir head and is sort of a "books literate people have read" list. Apart from the futility of the task and the oddity of the list already compiled, what books would you suggest? My approach would be not to focus on "books literate people have read" which is near endless, but rather choose books that would be mind expanding and introduce new ways of thinking. So apart from the various Dialogues, I would suggest something like Taleb's Black Swan and Hofstader's Godel, Escher, Bach. Especially since the kid is already pretty well read in the humanities from what I can tell.