No, I don't have a 16-year-old myself, however, I was the problem-teen in my family and then went on to take child and family studies classes in college and learned some basic principles that I wish my parents had known when I was acting out. I hope these help.
1) Know you can't change your child (or your husband for that matter), but the ways you change your own behavior can result in your child (or husband) changing theirs. That said. . . .
2) Does your child *really feel like* he is loved by you? I'm sure right now you are incredibly frustrated/angry with him, and it probably shows in every look, word, and conversation (or lack thereof). It takes FIVE positive experiences (a smile, a kind word, etc.) to make up for ONE negative experience. (John Gottlieb's research on marriages) That's a lot, but try to start small. When you get up in the morning and meet him at breakfast, talk to him cheerfully and kindly. (Teen boys tend to like their space, so maybe a hug or kiss goodbye would not be the best idea, so stick with your conversation and the way you ask him to help out around the house. (do you order him, or do you ask him politely?) Start focusing on the good things he does and point them out, rather than focusing all the time on the bad. Thank him for helping out his sister, or any other tiny good thing you see him do. However, beware over-doing it!!! Start out slowly--one comment in the morning, one in the evening and work your way up--so he doesn't think you're just being weird or something.
Oh, I just remembered. There are five "love languages", ways that we recognize love: time, touch, service, kind words, and gifts. Typically we show love in our own love languages. Watch how he usually shows affection to others and try to show him love in those same ways.
If your child doesn't feel like you love him, he's not going to trust you. If he doesn't trust you, he's not going to listen to you. Additionally, he may go looking for love in the wrong places, as it sounds like he may be doing already.
3)Apologize to him. Yes, this may sound crazy, but teens are amazing at noticing and magnifying any adult misbehavior. Forget about all the ways he's misbehaved and consider yourself. Have you lost your temper at him? Did you say you'd give him an allowance if he did his chores and then not followed through? Think long and hard to see if there's anything that you may have done that could be upsetting him. Then, sit down with him, and apologize for whatever it was. Don't try to justify your behavior, but it's fine to show your concern for him. (e.g. "I'm sorry I've been really harsh on you. I've over-reacted a lot, and I shouldn't have. I guess I'm just really worried about you. I hate to see you making decisions that will really hurt you in the long-run.") Sincere apologies go a long way in helping a situation. However, you also have to commit to changing that behavior, and believe me, he'll expect you to keep your word. If you do, though, that will start building the necessary trust between the two of you.
4) Avoid lecturing and nagging at all costs. If you taught him when he was younger or have lectured him many a time before, he already knows full well when he makes choices you disagree with, so there's really no point in bringing them up again, unless you really want to continue arguing with him, which is not recommended. Nagging and lecturing are the first way to de-motivate your child from doing anything beneficial. If there's something you'd like him to do for you or someone else, be sure to ask him politely.
5) After he starts to seem more relaxed around you, start finding out what his dreams and ambitions are. What is he passionate about? sports? art? drama? science? Find ways to support him in these things. Has he made the connection between needing good grades--in all of his classes--and making it to college? If it doesn't seem like he has, find a moment to point it out in a very matter-of-fact way, not accusingly! Let him know you'd be glad to help him out in the subjects he's having trouble with or help find him a tutor or someone he can study with. If he's having problems with teachers, work out with him ways to solve those problems or help him get into different classes. Ask him if he'd like for the two of you to get together with a teacher to work something out.
Hope this helps!