How Jack Skellington Is the World’s Most Lovable Problematic Skeleton

A picture of Jack Skellington with the words,

Athena ScalziIt’s that time of year again when The Nightmare Before Christmas is finally socially acceptable to watch, and thankfully it will remain in season until Christmas, because it is a wonderful film that doubles as both a Halloween and a Christmas movie. Though if you’re anything like me, you watch it far more often than just around the holidays.

You may remember I did a post about The Nightmare Before Christmas back in 2018. However, that post was only to express my adoration of the movie and tell you all it was my favorite. So, with the knowledge that it’s my favorite, let’s explore why my favorite character in my favorite movie of all time is actually kind of dick. And of course, spoiler warning (but it’s been almost thirty years since it came out, do you really need a spoiler warning after like, ten?).

Jack Skellington at the Halloween Town town hall.

Let’s talk about the fact that throughout the movie, it’s made very clear that Sally loves ol’ Bone Daddy. And she loves his presentation to the town over Christmas! That is, right until he swings back into Pumpkin King mode and describes Santa Claus, or Sandy Claws, as the monstrous ruler of Christmas Land. You can see the admiration and wonder on her face be replaced by a disturbed look.

So when the town starts getting ready for Christmas, Sally has some concerns, and tries to talk to Jack about them, but the boney biatch doesn’t listen. She tries to warn him of her vision, but he’s too obsessed over giving her a task to make his suit. He dismisses her worries about his “grand” ideas and then talks over her the entire time, until he basically says “okay I’ve given you your task now leave and get to it” without taking the time to hear her out. He never asks, “why do you think this?” or “what makes you feel this way?” He’s just so adamant about what he wants that he doesn’t give her the time of day.

I’m not sure about etiquette in Halloween Town, but Jack literally had three children kidnap someone. Verbatim, just straight up snatch and throw him into a trash bag. That’s pretty messed up! Spooky skeleton or not, you can’t just nab someone (even the music for that scene is called Nabbed). But, Jack feels literally no remorse about it, and you can tell by the way he steals Santa’s hat right off his head before the kids shove him back into the bag after presenting him to Jack.

It’s only after he ruins Christmas, gets blown out of the sky, and saves Santa and Sally that you can tell he feels bad. Jack apologetically hands Santa’s hat back to him; Santa yanks that hat out of Jack’s hands, then reprimands him for not listening to Sally.

(Also why do the kids just get off scot-free even though if they hadn’t given Santa to Oogie Boogie none of that would’ve been an issue? Jack specifically said to “leave that no good Oogie Boogie out of this!” But whatever, this isn’t about the kids, and their song about kidnapping Santa was fantastic, so I’ll let it slide.)

Jack Skellington in Christmas Town.

So, obviously, the big glaring problem with Jack and what makes him such a dick is that he tried to take over an entire other holiday, simply because he was bored and discontented with his life, and he felt he could, and even should, as seen in the quote from the song “Jack’s Obsession,” “And why should they have all the fun? It should belong to anyone. Not anyone, in fact, but me!”

It started out with a child-like wonder, and then grew into an admiration and love of everything Christmas Land had to offer. He loved the colors, the gifts, the decorations, the tree, everything about it. And then he tried to take it, and do it all himself, and just erase Santa out of the picture entirely and make Christmas his. And that’s what we call appropriation.

Being the ruler of one holiday wasn’t enough for ol’ Jack, the selfish skeleton wanted another one, but still wanted to keep his, too. That’s like the worst part, it wasn’t even a trade, he didn’t offer Santa Halloween, he just took Christmas and kept his own holiday on top of that. That’s a dick move.

Of course, by the end, Jack realizes his mistake and feels bad, and defeats Oogie Boogie and apologizes to Sally and everything, so he’s not a total dick. He was just misguided. At least that’s what I tell myself so I can still love Jack and The Nightmare Before Christmas as a whole.

Jack Skellington and Sally at the end of the movie.

Let me know in the comments if you think Jack was a total ass (and that Sally deserved better), or if Jack is just a lovable scamp, or somewhere in the middle. And have a great day!

-AMS

31 Comments on “How Jack Skellington Is the World’s Most Lovable Problematic Skeleton”

  1. Hi Athena — great essay and I love when we see people casting an eye over things they love to see if they hold up. NBC is a lovely movie — I’ve loved most of Burton’s reperetoire — but yeah, Jack is a jerk for much of the film!

    I find I’m tiring of “misguided” characters in media… it feels like the writer wants it both ways: they want us to be able to revel in the bad behavior that we all wish we could get away with, then in the end excuse them (and ourselves!) that they (we) are really good and meant well. Even in this case, saying “misguided”… guided by whom or by what? If it’s our own internal desires and whims, then it’s more “I made bad choices”, isn’t it.

    Good writing, good thinking… keep it up!

  2. “…do you really need a spoiler warning after like, ten?).”

    Yes, because there are still people out there that don’t know that Darth Vader is Luke’s father. Oops! Sorry! SPOILERS! :)

  3. I entirely agree that Jack is an appropriative jackass. I also think the movie can be a comment on the benefits of shared culture. Jack is improved by his exposure to Christmas (once he realises that it’s not his to take over entirely) and also develops a new appreciation for his own.

    This is a half-developed thought, I realise, but I’d like to think that the answer to the dubious appropriation is something about multicultural appreciation.

  4. Yes, I agree. I like that Sally is feisty and keeps on going despite the odds. It does have a bit of the female trope of being smarter than the man and cleaning up after him. At least, it’s not as bad as the fantasy that a good woman can change a bad man into a good one. Jack was a really big jerk here and luckily, forgiven.

    I still find it charming and think that it isn’t as bad as some other cultural norms expressed in movies (Twilight?). It’s one of our family classics, anytime of the year we please. Totally fantastic soundtrack.

  5. I wholeheartedly embrace the thought of redemption and forgiveness by loved ones when we do majorly frack things up. I hope that’s what my kids get out of it.

  6. TNBC has been one of my favorite movies since I saw it in the theatre as a teen.
    The Jack and Sally thread was always my least favorite part. I felt like why does she even like him? Is this pseudo-romance even necessary to the story? It irritates me when movies directed at kids force romance.
    The main themes are redemption and self acceptance. So, yeah, Jack acts like a jerk when he wants to be something he’s not but when realizes that he is fine the way he is he is able to undo his mistakes. It’s a beautiful messages and why I love this movie!

  7. I love Christmas. I love Halloween. But never got the movie. Tim Burton is an aquired taste that I never got.

    I also thought he sold out to Disney on Dumbo. For fans of Burton, it didn’t strike me as Burton.

  8. Spoiler alerts are relevant forever because new people are born every day, and everything is new to them. It’s only respectful to grant them their spoiler warnings, even for old, obvious things.

  9. I’d go with somewhere in the middle. Misguided, absolutely. The question in the end is, does he see the err of his diabolical ways? Sally is obviously in love with the man but does she deserve better? Ultimately that’s a question for Sally to answer. Love is a funny thing.

  10. I’m always irritated when a relationship is completely one-sided and then that character is rewarded for it at the end. Sally spends the whole movie pining for Jack despite him being a) a criminal b) a jerk and c) totally dismissive of her, her feelings, and her affections. Yet the lesson at the end is…keep up the Eponine-in-Les-Mis-style pining, girls, because eventually he will notice you!

  11. I have enjoyed this movie . . .but I only ship Jack and Sally because all her other options seem to be even worse. It is another cautionary tale about men who fail to listen to the women around them. A tale as old as Cassandra, I’m afraid.

  12. From a writing perspective, Sally is the hero of this movie. Jack barely changes. Sally has the clear antagonist. Sally wins the heart of her beloved. (Even though he sucks.) That Jack is the big hero somehow because he goes from bored to less bored drives me up a wall.

    My friend recently called this “Appropriation: The Movie” and I can’t stop thinking about it.

  13. You pretty much nailed all of the reasons that this film did not resonate with me as it did for my college roommates (yes, I am “old”) when it was released, and why I know that I could have been a much better boyfriend for Sally the singing seamstress.
    “No, I think not, it’s never to become, for I am not the one.” {sigh}

    But I digress.
    Oh sure, it IS a fabulous piece of stop-motion animation with the full talents of Danny Elfman and Tim Burton fully on display but the protagonist is as much a Grinchy villain as he is a misguided anti-hero, right down to the lovable dog sidekick. The whole endeavor is about Jack getting his way, completely based upon his vision, without regard for the literal vision that Sally tries to warn him of. It took me a good decade or so to realize that his boredom with what he had and then passionate embrace of this next new thing was just classic juvenile male behavior right down to the risk-taking behavior. Then I was able to reframe the film as a coming-of-age piece where Jack makes some poor decisions, has to live with the consequences, and learns the value of real friendship. After that, I am on board with the twofer holiday classic. I don’t love it, but now I have probably seen it at least as many times as “The Fifth Element.”

  14. Hmmm, I may have to rewatch this. It is old enough that I saw it before I met my wife of, currently, 25 years. My then girlfriend and I went to see it to decide if it was appropriate for her then 6 year old son to see. I was firmly in the ‘no’ category which caused our first big fight (which probably should have told me more than I detected then) Due to that, the movie has always had a certain odd memory for me. My wife knows of this, but has no desire to see it for any reason. Maybe some night when she is out I should rewatch it. Maybe not, but maybe.

  15. I like it mostly for the songs and art. Also the kids-opening-gifts scenes.

    Yeah, Jack is a total dick for almost the whole movie. He doesn’t listen to anyone, and even when he literally comes under fire he thinks it’s a compliment. He makes up a propaganda version of Santa Claus, The Sandy Claws, to justify his appropriation.

    In short, he’s a Republican.

    Favorite songs: What’s This and Kidnap the Sandy Claws.

  16. Thanks for a great post.
    I loved the movie when it came out (30 years, really !?), and still think it’s fantastic.
    I hope to see it again this year.

  17. I spun this to my first grader as “Sally saves Christmas and teaches Jack to let other holidays alone and be with his friends.” So the OogieBoogie scene is “when Sally and Santa distract Oogie so that Jack can untie the magic bag of bugs” and Santa can re-do Christmas.

  18. A major point of the film is that appropriation, done poorly and without dialogue, is wrong. Another is that people in power need to listen to everyone, and especially women, who have been marginalized (Sally is the DOctor’s Angel in the House who becomes a Cassandra figure). It also warns about burnout (because of neoliberalism, exemplified by the prizes the mayor gives out), unexamined lives, and narcissism. The film is a morality tale.

  19. I always hated the movie. Too problematic for me from the start, and I’ve never seen any reason to be an apologist for it. Yes, you sure can write a catchy song about any level of abuse; why does that somehow make it better?

  20. Okay, so this closely correlates with a philosophical discussion I was having with myself. Today, I went to work in Rural Town, OK. It really doesn’t matter which one, they are all a different planet than the city. In the city we are well aware that certain companies are destroying our way of life, and everyone I know in the city including those working for those companies will do whatever they can to slow them down. It is our way.

    I go down to Rural Town, and the rules are quite different. Poverty is a much bigger threat there. People can’t take a moral stand, they might starve, or lose everything.

    So the line that gets me is; “That’s our job, but we’re not mean, in our town of Halloween” and instantly I’m transported to the town I work in. Everyone I have met down there are really loving and kind people in one way or another. They make us city folk look like jerks. They work for people however, who I have no respect at all for. Some of the work they do is terrible.

    That’s my perspective on the company town in Nightmare Before Christmas. The only industry is being scary, kidnapping someone is scary. That’s the whole joke premise of the movie; they don’t know how to operate a purely compassion and candy filled holiday. I think they would know something about Christmas shopping, but the movie skips that.

    TLDR; Any culture can and will look absurd without appropriate context, and in an hour and a half movie, you aren’t getting that.

  21. For the past several years, every time this movie comes up, I spend a bunch of time on YouTube watching Grace Jones videos, because Jack’s walk always makes me think of the staircase climb in “Demolition Man.” As for the movie itself, I both enjoyed and was annoyed by it, and I think you’ve put your finger on why. Meanwhile, off to YouTube…

  22. I think there’s two very different ways to look at Jack.

    One is to interpret him as human, in which case yep, he’s so caught up in his own enthusiasm for the shiny new thing that’s hauled him out of his funk that he acts like an insensitive ass. Or more accurately, he’s so caught up in *himself* – he’s self-centered, everything revolving around his perspective and emotions, even when what he’s trying to do is bring the novelty and joy he felt to others. His hubris and pride go before his (literal) fall, in classic style.

    The other is to interpret him as a member of a town of amoral monsters whose job – and arguably raison d’étre – is to terrorize people. “We’re not mean” doesn’t signify “we have well-developed senses of ethics and restraint”, it just indicates a certain lack of *malice* behind the horrifying acts. (And it’s pretty clear that the lack of malice isn’t universal, given Oogie and henchlings.) In this light, Jack’s actions aren’t beyond any sort of pale, he’s just veered a bit off his usual archetype into something more mad-science-y. Casually kidnapping someone? Gleefully stealing something that others hold dear? Obliviously pursuing a mad scheme over sensible objections? Yeah, that all seems pretty Halloweentown, especially if there’s no intended lasting harm.

    IMO, the movie makes way more sense with both these interpretations kept in mind, rather than just picking one or the other as “the correct one”.

    Given that, Jack’s post-disaster regrets aren’t only a human realizing, “oh crud, I was a total self-centered jerk”, they’re also a monster taking a few steps towards a more human / empathetic point of view, which is, I think, a slightly more impactful / hopeful ending.

    (Oh, and I have no idea why Sally’s fallen for him as of the start of the movie, and if a friend were in a similar situation I’d suggest she… not pin her hopes on the Jack-equivalent person having such a change of nature. But attraction isn’t really under our control, and given that she’s in love, from what I recall she handles it well.)

  23. I think the Halloween Town and its residents can be thought of some kind of Platonic ideal of Halloween and monsters, so being (at least on the outside) mean and scary is what they are.

    However they seem to have agency in what they do and can change. Jack has really no context of what other holidays than Halloween are, and kind of tries to impose Halloween on Christmas. I’m not sure how the different holidays never interacted at all, though.

    He’s misguided and I agree with the idea above that his behaviour is very stereotypical young man: rush into things, don’t take others into account, don’t realize the facts even if they fly in your face. The thing I’m most annoyed is why Sally’s into him – it seems like “she’s the only available woman so of course she and Jack will end up together”, which I don’t think is good storytelling.

    I still don’t hate the movie. We watched it many times with friends when it was newer, and a couple of weeks ago I watched it with my kid who wanted to see it. It wasn’t as good as I remembered, but it was still watcahble.

  24. The movie is amazingly wonderfully visual, which is really all I want in a movie, because otherwise the book is always better. So does the movie say, everything Jack does is wonderful, or does it say, yeah, Jack is a jerk, and how’d that work out for him. I think it leans more toward the latter.

  25. I hadn’t considered the cultural appropriation angle before (why, yes, I am a straight, white, cis male, how ever did you guess?).

    Viewed through that lens, I think the movie is quite anti-appropriation and pro-appreciation.

    Initially, Jack tries to steal Christmas wholesale and apply the superficial trimmings to Halloweentown. He doesn’t understand the meaning behind anything he’s doing or wearing, he just knows that doing the thing and wearing the thing will mean he gets to do Christmas. As expected, this is a disaster for pretty much all involved.

    At the end, Jack finally listens to Santa and starts to appreciate Christmastown’s unique culture. He stops viewing it as “this is new and interesting and must be mine” and sees it as “these are fascinating people, and I want to learn as much about them as possible; maybe they can teach me some things I can use to improve my own situation, too”. Jack starts to appreciate Christmastown’s culture, and becomes a better Pumpkin King (and person, especially with regards to his relationship with Sally) for it.

  26. Analyzing TNBC in ordinary terms seems quite bizarre. It’s simply a trip. You’re supposed to hang on for the ride and let it tickle your senses and mind. Boxing it up in checklist categories means you’ve mostly missed the point.

    As for spoilers and time dates, I’ll refer you to the 1973 Peanuts that spoiled the big reveal of the 1941 megaclassic “Citizen Kane”. That was 32 years later. The cartoon is perfect if you’ve seen the movie, and absolutely despicable if you haven’t. (No link to an online copy provided, obviously.)

    In fact, Shulz revisited his “Citizen Kane” spoiler strip in 1995, and produced a variant that was spoiler-free! https://www.gocomics.com/peanuts/1995/10/08

  27. Agreed 100 percent!

    Even as a kid (I had to have been about nine when the movie came out) I was irritated at the potential and actual consequences of Jack’sactions.

    Christmas gets ruined (even if only temporarily) for everyone and Santa is nearly killed.

    Boo on you, Jack

    And yes; Sally deserves much, much better. Watching her go from a creep of a father to a dismissive jerk would have ruined the movie for me.

  28. I always thought that Jack being a jerk was part of Halloween Town’s general ghoulish vibe. They’re all lovable bad guys over there, not just the Pumpkin King.

    Personally, I find Jack’s unearned leadership privilege and the fact that he bosses around the denizens of Halloween based on nothing but a vague and unexplained hereditary title more problematic. He controls the means of production and puts the labor to work to foist an excess of bizarre and unnecessary consumer goods upon an unwilling populace. Kinda like our own failing late-stage capitalism.

    Nightmare is one of my favorite movies of all time. I watch it every Christmas season.