I think with such a short list, you have to think less about 'what are the classics?' or 'how can I be as subtly subversive as possible?' and more about, what is it that I want schoolchildren to learn, and which books embody those lessons best?
I'll go ahead and get my first selection out of the way, because it's so automatic for me: The Giver, by Lois Lowry. I first read it as part of the curriculum in my ninth grade English class, and since then it has been my number one favorite book. Sure, it's for kids - but see, it's not. No other books outside of the philosophy and sociology books in my collection have given me so much to think about. Utopia is a tricky business that can't exist without a dark side, and Hollywood depictions, especially, mainly focus on the dark side ('see what evil lurks beneath the facade?!'); unfortunately that wipes away any chance of wrestling with a concept that we, tellingly, keep coming back to.
As contemporary readers, older schoolchildren can ask, what things in my world were done away with to create the Community, and why? Do I agree that they were negative enough to warrant this, or not? What would the Community be like if they had allowed just this one extra thing, or that one? Is it possible to achieve utopia without prohibiting individuality, spontaneity, choice? Why or why not?
Ultimately I think the world of The Giver opens up the opportunity to think about the realities of today, and what is and isn't good and/or necessary for a society that benefits everyone.
(It's highly likely this book is already on the shelves, but...oh well. Just in case)
My second choice has been more difficult. I've been on a kick lately wherein I'll lament to the nearest person that 'kids these days' don't read books that are even half as difficult as the ones I read growing up, or the ones my parents read; really, the print just gets smaller and smaller as you go back, contrarily the books actually get longer, and the prose is more complicated. George Orwell convinced me years ago that language is the key to human reasoning, and the more complex the language, the greater one's ability to
So I can't very well then go and pick an easy book as my second choice.
It will, then, be Great Books, by David Denby. I ran across this book in a summer college course on teaching literacy in the content area, headed by a great old guy who encouraged us to bring a few books to class each morning to share. This is one that he actually brought, and I borrowed it and devoured it, and then bought my own copy later on.
Succinctly, Denby took two classic literature (Western Civilization) courses at Columbia as research for his book, and his observations coupled with commentary from the actual professors and students make for fascinating reading. The works range from Homer to Sophocles to Machiavelli, to Locke and Hume, to Shakespeare, Nietzsche, and Woolf.
I know earlier I said my criteria was not going to include 'what are the classics?' I will clarify and say that I was not interested in choosing one classic book. With that said, Great Books is a perfect choice for two main reasons: it helps direct the reader toward thinking more critically about not only literature but life, which is my wish and goal for all students; and it's an excellent survey of the classics if you haven't read them and a course is not available. (Also, the print is small and it's almost 500 pages)
All right then. There you have it. Now what two books would you choose?