American middle and high school student must reads?

Ricochet is trying to come up with a Book List, Teen Edition. Ursula Hennessey explains one problem she had:

For starters, I wonder if I’m the only dolt on here who had the following problem: I was asked to read Adventures of Huckleberry Finn before I knew anything about slavery, Animal Farm without grasping the most basic forms of government, The Scarlet Letter without really “getting” adultery, and Romeo and Juliet with only a modicum of understanding of my own English, much less that from 400 years earlier.

Then she poses the question:

What are 5-10 books we should expect middle and high school students to 1) understand, 2) learn some useful history from, and 3) learn a life lesson from?

What say you?