The Road to Destiny: Books for the Graduate

What books would you give to a young person just stepping out into the world? I started thinking about this as my seniors get ready to discover the world and themselves. Could I come up with a list of books that might help them carve a path both in the great world outside themselves and into their own souls? I'm a high school English teacher, so I know about short attention spans. The books I offer to the eager graduate must be compelling. My list can't be long: a long list evokes the specter of giving up. Ten is my arbitrary limit; I came up with a list, similarly arbitrary, that might help the graduate imagine the worlds without and within. The books on this list include fiction and non-fiction.  Many of the books on this list involve a main character struggling with issues of identity and formation of self.  A couple of the books on the list I simply think are irresistible for younger readers (or any readers).  Tell me what you think--I'm sure I left something off my list that you think is absolutely essential....

1. The Inferno by Dante Aligheri:  Dante was in the middle of his life when he found himself in a dark wood, but this spiritual journey all the way to the ninth circle of Hell never fails to capture the imaginations of my high school students.  I find that most have spent very little time thinking of sin and their souls, but the vivid imagery of this poem is irresistible, and young folks love to think about the larger ideas of good and evil.
2. The Narrative of Frederick Douglass:  this is one of my all-time favorite books.  If it were simply about the evils of slavery I wouldn't come back to it again and again, but Douglass shows how perfectly nice people are corrupted by the evils of an unjustifiable and criminal system.  The narrative also has a powerful lesson of the importance of literacy, and the ability of one man to form himself through the power of reading and writing.
3. Frankenstein by Mary Shelley:  what does it mean to be human?  What do we owe to those who love us?  This amazing novel has nearly everything in it:  monsters, both human and inhuman; the inhumanity and arrogance of power over others; an exploration of childhood and learning; and vivid, powerful imaginative writing.
4. East of Eden by John Steinbeck:  I know this book is long, but people from every walk of life claim this as a transforming book, a favorite book.  A powerful, primordial, mythical story about sibling rivalry, love, and the absence of love.
5. Persuasion by Jane Austen:  what happens when the one person you could love slips away from you because you were too young and too impressionable to think for yourself?  Is it possible to change a life-altering decision?
6. Black Boy by Richard Wright:  this is a classic novel of the journey from innocence to experience.  Set against a background of social injustice and suffering, the novel is also the story of a writer's intellectual self-education.
7. The Heart is a Lonely Hunter by Carson McCullers:  for the small-town misfit, a beautiful and evocative exploration of loneliness and belonging.
8. Rule of the Bone by Russell Banks:  this is the story of a child marginalized by a family and a society which all too easily abandon him as incorrigible and not worth saving.  The main character, Bone, finds a mentor and takes a spiritual journey against a disturbing backdrop of neglect and exploitation.
9. A Prayer for Owen Meany by John Irving:  another long book that draws the reader in and compels completion.  The question is, does each of us have an irrevocable destiny? 
10.Into the Wild by Jon Krakauer:  I was going to put Walden on this list, but this book is one that asks some of the same questions that Walden does, but with a different sort of urgency and more tragic consequences.  Christopher McCandless was a wealthy college graduate who walked away from everyone and everything he knew.  Why did this young man drop out of society, and what were the tragic errors that led to his death by starvation.  This non-fiction book reads like a novel, and asks more questions than it can answer.

I'm eager to get your feedback, dear readers.  What books would you hand to the recent graduate (high school or college) to help them navigate their inner and outer roads to destiny?