What are the top ten or twenty books you feel a young, black man should be reading?

What are the top ten or twenty books, you would suggest, a young black, fourteen year old man should read that provide engaging, opposing view points on the identities of race, gender, orientation, poverty, prison, addiction, single motherhood, fatherhood, marriage and respectful relationships, consensual sex, feminism, religion, culture, politics as well as being an adult, in America, in the twenty-first century community accosted by all the issues of our time?

The perspective I want to approach this question is that the titles I am looking to collect should address the groups of young men who do not care to read, do not read or are readers who are challenged by their skills or education. I am not looking to preach to the converted, I am looking to influence the ones who need to be reached. I am looking for books that guide readers to address conflicting philosophies so that they might develop their own ideas based on opposing viewpoints.

I am looking for books that will help a Christian young man see through to eyes of Muslim. I am looking for books that will open the eyes of a people who are troubled by or promote bias, in their community, because of darker and lighter skins tones, physical appearance, sexual orientations or mental health.

The initial motivation is that the holidays are soon and I am looking for suggestions of books to buy. I would prefer to not just buy¬†The Autobiography of Malcolm X and The Invisible Man, I want to build a broader perspective of a collection. I realize that this could be a very engaging topic that could grow, on its own, into something more important than consumerism. Do you feel that compiling a list of books is worth the time? Would you care to point out things or issues that I haven’t addressed or that you feel should have been addressed in a better way? Thank you for taking the time to respond.