I believe in bibliotherapy, that reading something you can relate to can help you heal, grow, and learn.
The boy loves skateboarding, likes video games and hip-hop, and is madly in love with his girlfriend. He makes friends easily and can show compassion. He likes sports, plays in the playground, but hasn't joined any teams. He's a C student, but could be a B student with some effort. He can read and write, and has shown good insights into literature. However, he lacks some common world knowledge, such as where Rome, Italy is. He hates to read.
He's a virtual orphan: his mom died of cancer nearly two years ago, and his dad abandoned the family years ago. His uncle, a musician and a former teacher with a genius I.Q., takes care of him. The two clash a lot. When he was younger, the boy would watch movies or TV and speak the dialogue along with the show. Sometimes he still does. He's African-American, with other things thrown in. He lives in an ethnically-mixed, working-class neighborhood. He had an incident with the law, and had to do community service. These days he'll say "I don't care" to a lot of things, but I think that's just a defense.
I think learning to love reading--at least sometimes--would open his mind and soul to many good things. So, what titles--books, novels, plays, poetry, what have you--might be good for him? What might engage him, interest him? I'm also open to suggestions aside from reading. Thanks for listening.
Answer on How to interest a 16-year-old boy in reading...?
I teach middle school students and we have a reading program in which each student is expected to read at least an hour daily. It's tough to get a lot of the male students to read, but if you can find the right book or series, I've seen kids finish books in a week and then go to the library asking the librarian for the next book in the series.
A book that never fails to interest my students is SE Hinton's The Outsiders. There's a lot of themes that relate to young boys- loyalty, being a social outcast, class conflict, love, etc. If he likes that, he can read SE Hinton's That Was Then, This is Now, and Rumblefish.
Also, Walter Dean Myers is a great author who has a lot of books that would relate to a young man.