What. A. Fucking. Quote. His undying passion to save people, even if it means doing the impossible, is both his greatest trait and his biggest doom. You can't save everyone. He knew he couldn't save Rollo, but he made the promise because it was the singular, strong act he was left with in that moment. For him to not even try would have meant he gave up, but it is because he tried that he will carry the guilt for not succeeding forever.
I'd vouch this scene shows the exact similarities and differences between Vash and Wolfwood. They both know Vash failed.
Vash looks back at his failure with bitterness and guilt. Wolfwood, with guilt and blame, because the promise was "made empty".
They both know it would've been impossible to succeed, but neither of them gives it importance to even mention it, because reality is too confusing and cruel to accept
The parallels between how they call out in agony towards their loved one at the end of the road...
Vash's "行かないで!", an emotionally overwhelming plea. Nai's contrasting "行くんじゃない!", an expression of disbelief, a selfish "How dare you leave me?", a desperate grasp to manipulate Vash, to have control one last time.
Vash's emotions towards Wolfwood are very important in this scene. There are probably many ways to interpret it, but this is how I see things :
While Wolfwood doesn't follow Vash's policy that all lives are worth sacrificing for, he does have certain lives he'd risk something precious for. Not many people would do that. Vash is in awe about finding someone who does, he sees his good traits in Wolfwood, but Wolfwood fights back with his title ("The Punisher'), highlighting that he's not doing this because he's 'good'.
Because someone who bears his history, his title, his identity is not someone who will ever be captured as good, no matter his intentions to sacrifice more than others ever would (in this case, the person he loves - Vash), and Vash understands what it's like to be labeled as bad and to fight regardless. It's an unrewarding, mortifying ordeal, but it's his way of life, and he's no longer alone through it.
Dropping my list of all the characters I strongly headcannon as transgender since no one asked
If anyone is actually interested, I also have a list of reasons for each of them :
There are many different reasons why a character would be headcannoned as trans. Personally, I usually hc characters as trans because their narrative reminds me of the trans experience on a very personal level. (There are also instances of "RAFHHH they just give me the vibes" but I didn't add those to the list)
Let's expand by putting characters in categories based on how the headcannon came to be:
#1. They are "weird" and neurodivergent coded
(Hunter, Luz, Laios, Nene Kusanagi, Huo Huo, Ash Fox, Randy Cunningham, Juwan Park)
It's pretty common for trans folks to also be neurodivergent. Sometimes you just can't have one without the other ( ◜‿◝ )♡
In Luz' and Laios' case, there is also the "shunned by other people for their traits" part to add to the equation :/
#1.5. they're weird and they simply do not give a fuck
(Alhaitham, Anaxa. I could even add Dr Ratio If I felt brave enough)
I had to add them to a different category cuz they hold a special place in my heart. Its that sort of positive trans headcannon. They all know theyre weird as hell but they appreciate themselves for what they have (knowledge) rather than what other people deem as "lacking". I fucking love them for it. I aspire to be like them. To see them through the trans lenses motivates me.
#2. They are never satisfied with themselves despite being a hard worker
(Stark, Dipper, Izuku Midoriya)
Trans folks are more likely to push themselves to "make up for what they lack" because they feel like their identity makes them less.
For example, with Dipper it's how he always tries to prove himself as manly, and with Deku it's how he hurts himself in the process of using his powers to save others because he doesn't want to dissapoint the people who have faith in him becoming the n1 hero.
#3. They look up to their male partners a little too much
(Reki Kyan, Akito Shinonome)
They obsess with comparing themselves to them, with pushing themselves to make up for what they naturally lack. It's very usual for trans folks to compare their gender journey to one of a cisgendered person. It's unhealthy, but it happens more than one would think.
#4. Their best friend/lover is trans so Im making them trans too cuz I dont want their best friend to be alone/cuz I like to think they can motivate each other on their trans journey.
Durin (for Scaramouche) - I like to think of him as Scara's parallel and it brings me joy to think Scara would have someone to both teach & learn from about the trans experience.
Yong-Mi (for Hyun-Ju) - "You're beautiful too, unnie" she said and I was then shot 57 times.
Rui Kamishiro, for Mizuki Akiyama - Just because! Also, he's very ND coded so ig that goes for category #1 too!
Todoroki Shouto, to Izuku Midoriya - I think Shouto can be considered a trans coded character easily because of the way he supresses his nature to spite his family, but another big part of my headcannon comes from what Deku said to him about his power being his. Afterall, Deku genuienly believed it when he said it because, he, too, has been power that he didn't expect, that he doesn't have under control, but that he wants and loves. From this scene, the two of them continously remind each other to treasure their powers and strive to be the best versions of themselves. It reminds me of the euphoria and sense of belonging of a trans friendship, so... there it is!
Serizawa Katsuya, to Reigen Arataka - there's just... so much text about Serizawa being manipulated and taken under the wing of someone who "understood his powers" and "saved him from being a hikikomori", but who turned out to be an asshole who only wanted to use him. Then, Reigen saved him, offered him a real job because he genuinely had faith he could stop being a hikikomori, because he genuinely believed his powers could be used for something good. If Reigen Arataka wouldnt do a wonderful trans role model, I don't know who would.
David, to Tabitha and Courtney. It makes me happy to think the girls helped him explore his identity when they became friends. They're all weirdos together and I adore them.
Sunny, to Kel. Just because :)
#5. They have a history of being shunned down/abused/abandoned by their family
(Max, Teruki Hanazawa, Marie Kim, Sunday)
Unfortunately, many trans people go through abuse,e even from their own families. As I like to say, If we don't have representation, then we'll make it ourselves (。・ω・。)ノ♡
Im also just comforted to see how all these characters found their happy ending despite the trauma.
In Sunday's case, it's the whole "trapped in a cage" ordeal. You oughta let the bird free, twin. Sometimes you oughta be a he/she/they, twin. Tim should perhaps be added to this category too because of the neglect :/ i see myself in him cuz of his anxiety disorder, also, so thats my reasoning for adding him to the list. He would probably fit more in the "I just hc him as trans cuz I feel like it" category, now that I think about it.
#6. Trans family/found family crumbs
Trigun poly - in Vash's case, it's quite accurate to hc him as trans because he's a plant and plants are genderless. The others are kinda just based on the vibes honestly. Wolfwood's extra yummy to hc as trans cuz of the religious guilt, the orphanage life, and cuz he always looks out for other orphan kids since he sees himself in them. The insurance girls are the epitome of feminity to me and it brings me joy to think of two trans women being that. Especially if it turns the polygon into a nice, warm trans blanket.
Seirei & Teruki Hanzawa - we've already established my reasoning for trans seirei. Teruki is a hardworker who always looks out for others despite being hurt and abandoned by the people who were supposed to love him. With this in mind, like to think of Seirei as parental figures/trans role models to him (*˘︶˘*).。*♡
Astral Express trio, Kel & Hero - just because it makes me happy :)
#6.5. t4t crumbs
Leorio & Kurapika, Yunli & Yanqing - yummy t4t (its not just this, though. I would actually be able to make a list of good reasons why I hc as them as trans but I don't rlly have the resources or brain power rn)
#7. I could literally write a 20 paged analysis on my headcannon. There is SO much material to work with with them
(Furina, Scaramouche, White, Yoshiki & Hilkaru)
Scaramouche and White are the ones who I'm most obsessed about. They got abandoned by their parents for not "being to their liking", they literally juggle with identities like its nothing, they canonically, changed their names, there's found family subtext, literally how could I not headcannon them as trans.
Theres this l post explaining Furina's transgender coding that I totally recommend if u wanna see good insight on that.
Im gonna come back to write about t4t Yoshikaru another day because BOY do I have a lot to say.
#8. Snufkin
I can't exactly say its just "based on the vibes" with him, but I can't say I have an elaborate list of reasons either. I guess it just brings me comfort to think of Moominvalley, a place full of acceptance, even created by a queer woman, to have no problem including a trans character. Basically : it just brings me comfort to think of him as such.