Your son is having fun doing what it takes to “make it” in the popular crowd. Being popular in high school is fun and has a ton of advantages even beyond high school (trust me as someone who was very much so NOT popular). The main issue is balancing belonging to a good clique with risks associated with the behaviors that are “cool”.

Sex is cool until your teen gf is pregnant.
Egging houses is fun until the homeowner comes outside and shoots someone.
Joyriding is fun until someone is injured in a car accident.
Drinking is fun until someone gies way over their limits and ends up in the hospital or worse.

This kid isn’t developing into a shithead or a bad person, but he is taking on some unnecessary risks. The fact that he keeps getting caught shows that he hasn’t learned his limits yet.

1. You need to figure out who his popular friends are. Not all popular kids are created equal. They could be the harmless type that just want to have a few beers and celebrate after the big game, or they could be in trouble with hard drugs because their parents don’t pay attention. If the former, let your kid have fun, but try to be better at supervising it and setting clear boundaries to reduce the risks of bad outcomes. If the latter, you need to coach him on where those kids are going. One self-destructive kid in a friend group can drag the whole clique with them. I had a close friend commit suicide at 15. Before hs was over, several other friends (myself included) had made attempts on our own lives. You are the sum of the 5 people you hang out with most. I needed a change of scenery and friend groups in college, and it helped me to be a better happier person in my 20’s. (Divorce was a big setback, though).

2. He needs punishment because he broke rules that are not arbitrary. I would recommend manual labor. One reason I didn’t get into much trouble in hs was I got caught in middle school. My punishment was manual labor where my dad would take the good tools away. I still had to get the job done, though. So, instead of using a lawnmower or pushmower, I had to use a weedeater to cut 5 acres of grass. Instead of using an electric trimmer, I had to trim all of the hedges with rusty dull shears. Instead of cleaning ditches with shovels, rakes, and a hoe, I had to use a trowel. Research paper for class? I had to go to the library and use encyclopedias and books because I wasn’t allowed to use the internet. These chores were my normal chores, but learning that tools were a privilege that could be taken away was a valuable lesson.

3. Spend time with him. I was scared of my father because he was a harsh disciplinarian, but he also made a lot of time for me and my brothers, both together and one on one. I spent a lot of time with him as a teen attending ball games and camping. I knew I never needed to act out for attention. If anything, I was trying to avoid attention from him and get attention from friends.

4. When I acted out, it was because I was lonely and thought I needed to do those things to make friends. I thought I had to throw parties and drink to make friends, and I was only sorta right. You can get a lot of superficial friends by drinking and partying. Everyone loves you when you’re self-destructive. I have never been more popular than I was last year when I was a barely functioning alcoholic going out and getting hammered every night. As soon as I cut back and started going out less, a whole lot of those “friends” vanished. Your son is probably just trying to fit in and thinks this is what is required. Show him that he doesn’t have to drink to get friends and be respected, and that anyone who’s only your friend when you’re drinking or paying for their drinks isn’t a real friend. It’s easy to mistake your users and enablers for your friends.

5. Explain realistic expectations, goals, and consequences. His social life is important to him, his future is important to him, and consequences follow people now…forever. It is so incredibly difficult to even make it into the middle class these days, and any bump in the road can all but doom one to struggle at the edge of poverty for much of their adult life. Being poor sucks. Show him how his behavior is opening him up to consequences that realistically lead there. Make sure he knows you’re invested in HIS goals, not just in whatever idea for his future you envision for him. Explain that your rules are designed to give him the best odds of reaching his goals, not that they’re meant to control or punish him.