The movie. With Kurt Russell?
I made you watch it.
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The movie. With Kurt Russell?
I made you watch it.

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married in every cinematic symbolic and alchemical language
castiel. tombstone
🫣🫣 i always say cas (and sam too) would strongly dislike a lot of the casgirl (and samgirl) opinions, especially regarding dean. but i’m thinking now that jack would also hate to see jackgirls dismissing his autonomy and absolving him of accountability and insisting he should just hate dean completely. when, canonically, jack has never wanted any of that.
💯 Jack doesn't hate Dean at all. He idolizes him (and I think Dean knows this and I think he's thinking, "Don't" because he doesn't see himself as a role model, but that's one of those things you don't get to decide). Jack understands Dean and only three days after he's born, is trying to emulate Dean's mannerisms, which is especially interesting given how angry and riddled with grief Dean clearly is. You'd think that'd be a turnoff for Jack, but it's not. Some people think Jack was afraid of Dean, but I don't. I think Jack was able to sense that Dean was a good man going through a hard time. He gravitated more toward Dean even though Sam was being "nicer" because he sensed that Sam was being insincere about his motives in the first few episodes and Dean wasn't. Dean was also showing and feeling his grief. Jack was grieving his own mother (just like Dean was) and Cas (just like Dean was) while Sam was trying to emotionally detach. Sam explains to Jack how hunter funerals work while they burn Kelly and Cas's bodies, but Dean is standing there feeling—hollowed out and lost. Jack knows better than to mirror Dean's grief 1:1, but his example shows Jack that feeling it is acceptable, and that Dean cares about Jack's dad (Cas) and the loss of his own mother, whereas Sam is doing his best to numb himself and ends up not being relatable to Jack because of that.
Jack overhears Sam and Dean's shouting match over Sam minimizing Cas's death/pretending it didn't happen so he can invalidate Dean's grief and I think things make a lot of sense to Jack then. Jack doesn't remember what happened before he was born— when he (or something pretending to be him) was communicating with Cas and Kelly. He's able to piece together a lot from Sam and Dean's fight about why Dean can't trust him and gets an even bigger picture over how much people mean to Dean. Jack models his mannerisms after Dean because Dean so visibly cares and feels, and Jack identifies with caring about people deeply and feeling so much that it hurts because Jack is also like that!
And I think you're absolutely right. Jack hates having his accountability denied. Even if it's not fair to him, Jack's dangerously explosive power is a reality, and he is ultimately the one who has to deal with it! And I think Jack also (even if it comes out in a largely unhelpful way) appreciates that Dean is more likely to take that seriously and even puts part of the responsibility of Jack's volatility on himself. There's a fight about Jack's volatile powers and his culpability in handling them very early on, after the Dodge City case, when Jack trying to flex his power proudly to Cas ends in a man being dead. Jack is already upset in the car ride home with Sam and Cas, but starts talking again when Dean comes back and reveals that he covered up Jack killing someone, and Sam says, "good".
SAM: How'd it go? DEAN: Usual. Killed the bad guy, saved the girl. SAM: What about the, uh… DEAN: Took care of it. SAM: Good. JACK: Good? How is that good? I killed someone. What was his name? The guard? Did he have a family?
Jack cares so much, and Sam says covering it up is "good", and Cas tries to tell him to ignore it—to put what he did out of his mind, but Jack isn't having it:
CASTIEL: Jack, don't do this to yourself. JACK: No, did he?
Dean is the only one who answers him instead of encouraging him to just not care.
DEAN: Yes, he did.
Dean knows denying that the entire thing happened or that the loss of that man's life and that it likely had broader impacts on his family won't make Jack feel better. Jack needs to be allowed to wrestle with the actual weight of his mistake and can't just compartmentalize it. Dean knows this, because Dean is exactly the same way. THEY GET EACH OTHER.
I think it's appropriate that this is where Dean tells Jack he was wrong about him and that Jack isn't a monster. But that isn't the only thing Jack needs to hear from someone (he's hearing a lot of that, actually!). The thing is for all Sam, Dean, and Cas might give reassurances in this episode that Jack's intentions were never to harm anyone and he isn't a monster, Jack knows that ultimately, lack of control of his powers still presents a danger that ultimately starts and ends with him. While that may present him with a burden that is unfair to him (because other people don't have to deal with what he's dealing with in that sense), it is nonetheless a burden he is forced by reality to bear, and denying the weight of that reality and how it weighs him down doesn't leave him feeling supported. It leaves him feeling unheard and alone. He doesn't want to be treated like a child with no culpability. He wants someone to take the dangers of what he can do seriously.

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DEAN WINCHESTER in one random episode per day ‣ 174/327 13.06 TOMBSTONE
I think you hit the nail on the head with 'gender non-conforming.' I think Dean feels compelled by the way John raised him to perform gender in a way that isn't authentic to him; that while there are so many different ways to be a man, he has been forced into the one that fits him badly. I don't read him as trans or woman-coded or whatever (and yeah, 'woman-coded' is so often just a slide into straight-up misogyny), I read him as being a man who is not 'stereotypically masculine,' but knows how to wear that mask.
Because, you know, men can like sexy pink satin, cook, care for people, be intuitive and emotional, admire and relate to women, and desire men. All those things are things a man can definitely do. And Dean does. I think he would love to not comply with gender, but he doesn't have time for himself in that way. He's too busy being god's favourite toy.
aww thanks! of course i agree about john's expectations of dean's behavior when raising him. but i think that's complicated by john both wanting dean to act in ways that are stereotypically masculine (teaching him how to use a gun at a very young age (1.18, 2.06, 11.08) and also saying things like, "that's my man" to an elementary schooler (1.18). but he also expected dean to do very stereotypically feminine things: frequent primary responsibility for feeding and caring for a child (i literally cannot cite all the examples of this godbless that is the whole show (to meeee)).
and i think that from what we've seen of dean's personality, the second is the one that comes much more naturally. he LOVES to cook and feed his family (and anyone). and while i definitely don't like the forced parentification or repeated forced responsibility dean experiences over the course of the show, i genuinely do think if given the choice, he would chose to care for and cook for and clean for his family in ways which are extremely stereotypically feminine.
and i think the way that that came naturally to dean and the amount of laundry, cooking, dishes, and sam's school-prep he did as a child probably made john lean a little harder on all the ways he wanted dean to still "be a man" etc. it can't have been easy for john, who already felt he was semi asking his kids to pause their lives so he could do his Hunt, to see dean to some extent pausing his growth into manhood by having to fulfill these feminine roles. i mean in 14.13, john emphasizes the normative hopes and expectations he had for dean. of course john wanted him to listen to rock music and was pleased when it seemed like dean was starting to sleep around.*
and of course dean learned to put on that mask.
i think it really is beautiful as the show goes on to see him let the mask go more and more. from little things like cooking lots in the bunker and wearing his special apron to his comfy purple pajamas - and in general more whimsical home clothes (noodle socks, scooby-do boxers, hot-dog pajama pants). to feeling he can express fear and discomfort with more ease ("always am" [scared] (15.16), not wanting to go in the tunnel (13.06), spiders (13.08), "never said i wasn't scared" (14.12), "hot bread" (15.20**). to his self confidence ("i'm good with who i am" (14.13), "lady, i'm tolstoy" (15.11), talking about retirement (13.23)) beyond his assigned role as value through self-sacrifice alone.
all of those signs lead me to believe that as time passes, as his life is less fraught with danger and conflict and death around every corner, he will have the time and space to heal and to bloom into more of the person he wants to be. and all signs point to that person being very different from the person that john, chuck, alastair, amara, gabriel, michael(s), zachariah, cain, crowley, even sam, and certainly anyone who values rigidly defined gender differences would expect.
(also your line about dean admiring and relating to women is SO spot on. i just have to shout that out. i just watched 2.18 and the way he is so impressed by tara's acting (speaking of acting and masks etc!!) is so charming to me. i said more about how dean sees and respects women's performances here. but yeah i loved how you said that!!)
*okay that one is from john's journal im sorry. but it tracks for me.
** this one makes me genuinely ill
look at how mindblowingly beautiful sam is in the cap they used in their thumbnail. from 13.06 i believe