Essential books for a school library

In a comment on the Otherbound review, Robert asked:

Suppose you could recommend 100 books for a high school library (ages 14-18). What books would you want the librarian to buy, and why? (Fiction, non-fiction… whatever you think it important for teenagers to read.)

I’m not sure I could answer this on my own, so let’s throw it out to everybody. What would you recommend as books that should be in any (American) school library? And why? What YA fiction would you want everybody to read, or which history or science books should a clever fourteen year old encounter? Anything slightly subversive that’s essential to becoming a well rounded adult?

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