This is a tough age, for this generation. So many in authority in many public places our youth go (like school & malls (neighbors etc) are breading and promoting anger. Many times our youth are labeled and thus give up. Ask questions? But don't drill him. Observe different attitudes and behaviors when around certain friends.
I have a 22 year old whose friends parents were giving them alcohol and leaving them home alone when they spent the night together. There was a teacher that lost his license to teach for five years for providing alcohol to minors. He even dated a girl the day after she turned 18 so they say. I know this because my son liked her went all this took place. He and this teacher had real problems. To the point the teacher came to my home to fight him.
Do not think that everyone in authority is a good person or influence. Keep praying, and What ever God tells you to do, do it! Your son needs to know the end of the road he is traveling. If you have opportunity to get him to see the end results of dropping out of school, not having a GED. Etc. Look up statistics on Dropouts and jobs. 
See if he can visit inmates through county programs (as in do a walk through the jail). Not getting to know them personally.
I will keep you in my prayers. I appreciate your openness and honesty. I hope this helps.
Kay 

Thank you all for your prayers and thoughts. My (now 16 year old) has moved back to live with his dad in colorado. I talked to him quiet a bit at first now and for the past three weeks, no one answers the phone when I call and no one calls back. I heard from his brother that he was in trouble for not going to school. I am still homeschooling my now 13 year old daughter. The only child left in the house. I do daycare and have a cat and dog. I keep all my children in prayer and very much love my church and church family. Again thank you for all your prayers and thoughts. God is great and keeps my life in check thank goodness. Love always and God Bless. Shawnna