I'm in the process of writing (for my high school seniors and juniors) a short Guide To Becoming a Civilized Human Being (alternatively, Self Help For Southern Californians). Basically, I'm trying to find disquieting alternatives to the inspid coming-of-age piles-o-poop normally read by that age group. Ideally, this will be a compedium of approachable works of philosophy, theology, poetry, and literature, as well as notes on how to read such works effectively. My goal is to select works which don't present too much of a language barrier, are more or less comprehensible on a strictly literal level, and which are likely to resonate with kids who are (albeit haphazardly) trying to fight the system, stick it to the man, and so forth. Here's a rough sketch of some of the initial prerequisites...

groundwork:

St. Augustine's Confessions
G.K. Chesterton's Everlasting Man
Antoine De Saint-Exupery's The Little Prince
Norman Juster's Phantom Tollbooth
C.S. Lewis' Till We Have Faces, That Hideous Strength
Plato's Symposium, Apology
Tolstoy's The Death of Ivan Ilyich
Evelyn Waugh's Brideshead Revisited

umm. Any other ideas?