Jack Skellington, Pumpkin King, even though he is a skeleton who lives in a graveyard and doesn't have any discernible ties to pumpkins at all, is adored and admired by all of Halloween town. He is a leader in his community, The Best at The Thing everyone loves. He also has an excellent dog. I mean, all dogs are excellent, but Zero's a good ghost dog. He knows to bring back the bones they play fetch with, none of this having to hunt it down yourself nonsense. He also has a jack-o-lantern nose.
Pictured: Happy ghost dog with jack-o-lantern nose who just wants to be your friend, Zero
Jack knows he doesn't quite understand Christmas since it isn't his culture, and when he can't "crack the code", he decides the solution is simple! He gave it too much credit and depth to start with! He rewrites the bits he doesn't understand with his own culture and preference. With the confidence of a white guy, he barges in starts trying to take over, ignoring the one person (Sally) who is trying to tell him "No, nothing about this is a good idea". He forces out people native to the culture he's stealing (Santa) and takes over, harming others in the process. Most of those toys attack and have teeth; people are getting hurt. Sally, being the smart one, goes to try and free Santa from Oogie Boogie because shit is hitting the fan. Because Jack is the hero and not Sally, this ends with both of them in danger.
When the military is called and are actively trying to stop Jack, his first response is to assume people are celebrating him, and he's confused and wounded that they don't like his take on their culture. Jack doesn't even think "Wow, I hurt people". He thinks "Well, I messed that up, but I had fun and everyone got a cool story out of it!" Then, after he reaffirms who and what he is, he thinks of getting Santa back so he can fix what he messed up. Better late than never, I suppose? This is the closest Jack comes to learning a lesson, realizing he's not good at a thing and should leave it to the people who are. He does not realize that he can't be good at this thing because it is not his culture, and he never grew up with it,of course. Just that he has his own that he's better at so might as well stick with that one!
He rushes home, finds Sally and Santa being menaced by Oogie Boogie, saves the day, Santa goes off to save Christmas--and I want to note here that it is Santa, on his own, who saves Christmas. Jack doesn't get to help. Jack realizes, now that he is alone with Sally, "Oh, she's been helping me and being sensible and not just worshiping me this whole time. Maybe we should date." I have no idea how ragdoll/skeleton sex would work, but we know Sally is at least somewhat modular, so... I guess it would be kinky?
Let's talk about Sally for a moment. She and Jack are apparently good friends. We see her looking out for and taking care of Jack repeatedly, and yet he doesn't listen to her or notice her home life is incredibly abusive. She has to drug the Professor to ever get out of the house. This is played off as "haha typical teenagers" but the Professor scolds her for this. He wants her around to take care of him and gets emotionally abusive when she wants to have her own life. The thing is, she's happy to take care of him! She is, by her nature, a caring and nurturing person! She just wants to do her own thing too. Not content to let Sally do her own thing, and realizing it's not just a phase, he literally locks up Sally. Jack goes to see the Professor he doesn't think to try and say hi to Sally, which means he is ignorant to the fact she is literally locked up just down the hall. We see her rip off limbs to get away from the Professor, and eventually she runs away. Which leads to her living on the street as she tries to hide from the Professor. Again, Jack remains ignorant to, even while having her sew for him and hanging out in his home.
I don't know what about any of this is supposed to be counter-culture, or why so many kids latched onto it as such. Aesthetics, I guess? Which was certainly the depths of "counter-culture" for most of the people I knew who were latching onto it. I still love this movie, but let's be honest: Jack is a self-centered, self-absorbed dude whom everyone worships for reasons that aren't totally clear and faces no consequences for his actions because there is a whole system in place to continue worshiping him. All he has to do is be moderately friendly and