First meetings: Wolfwood and Vash
ID: Wolfwood in his introduction chapter pinching a protesting Vash's chin with interest and exclaiming that people are stupid for not immediately recognizing Vash.
One thing I noticed while rereading the manga, is the nature of Wolfwood and Vash's first meeting; that is, Wolfwood isn't targeting Vash as his next mark, nor does he likely know that Vash is his next mark. As a result, I thought it would be interesting to look at how that shapes their relationship with each other in the beginning, especially in comparison to the differences in the anime adaptations. Just a fun lil tidbit to sink your teeth into.
Proof of Unknowing
For the case that Wolfwood wasn't yet targeting Vash, my first point is that it makes sense logistically; if Wolfwood was targeting Vash to kill him as Legato had originally told them to in the manga, it would be assumed that he would have tried to kill Vash. However, instead he doesn't try to at all, although one might chalk that up to Vash saving his life by spotting him while on the bus or some other plot gimmick for Wolfwood to not immediately try to kill Vash.
Secondly, and more obviously, Wolfwood hasn't met Legato yet. This is seen clearly when Legato asks Wolfwood if he's Chapel, who Wolfwood is (later shown to be) impersonating, which means that Legato has never met Wolfwood. As well, Wolfwood is only shown to know the location of his next job- when he mutters about the chapel on the top of the rock- and doesn't seem to know nothing else, making it highly likely he doesn't even know any other details. In fact, Vash actually warns Wolfwood to not get involved with Legato, giving Wolfwood his description, to which Wolfwood when recieving the info doesn't seem to know the man; and upon arriving, and meeting Legato, Wolfwood actually parrots the description from Vash's warning in wariness, recognizing him through Vash's warning.
ID: Collection of three manga pages.
First page: Legato comments, "'Chapel' seems to be missing... Well, no matter. Our target... Has yet to arrive." His words fade into Wolfwood exclaiming, "Huh?! A skull attached to his left arm?" Vash says, "Yep, yep! That's right. And a raised, needle-like torture device on his right shoulder." After a pause, Vash says, "You don't know him? Well, if you see him, let me know."
Second page: Vash tensely remembers a blood spatter and thinks, "Like a shadow, he came. And like a shadow, he killed and slipped away. If he... If he can move in and out of a crowd like that, people can be killed easily..." Wolfwood and Meryl look curious, and Wolfwood asks, "Well? If I see that guy, what should I do? You got a message for him?" Vash makes an exclamatory sound and shouts, "No! No! Never-mind!! Do not get involved. He's a very, very dangerous man. I swear!" Wolfwood laughs, "But I heard you were the most dangerous man in the world!" Vash sighs.
Third page: we see Legato and Wolfwood standing across from each other at their first interaction. Legato says, "That cross... I've been waiting for you. You're 'Chapel,' correct?" Wolfwood's expression is wary, and he says, "The skull... The torture device... I know you..."
Since Legato hasn't met him yet, this also means Legato's precious half-coins which he gives to each of the gung-ho guns hasn't been given yet to Wolfwood, which Legato has been previously shown to inform the gung-ho guns who their target is when he gives it to them (as with the first gung-ho gun). This again makes it unlikely that Wolfwood even knows his mark is Vash.
ID: A panel of Legato touching a broken coin in front of Monev the Gale, the first gung-ho gun and saying intensely, "Do whatever it takes. For twenty years of your master's benevolence, it's time to repay him."
Lending further support, when Legato mentions that they specifically may need to deal with--ie, kill--Vash, this is the moment when we are privy to Wolfwood thought processes, where he desperately rages against his life as a assassin and how he wants to escape this life that causes him to kill. This is especially understandable under the context of Wolfwood just being told that he is supposed to kill a man that he had just somewhat befriended, a man who had just saved his life and payed for his lunch, who clearly has a good heart.
ID: Two subsequent manga pages. Legato (off page) says "We're entering unknown territory here. You must be ready to handle any situation. Especially... Vash the Stampede. By no means may you fail!!" Wolfwood's frowning face is shown as Conrad comments that Vash is coming and that he understands why Knives chose that location. There's a close-up of Wolfwood's narrow-eyed expression before a cut to his shoes stomping up a mountain. He angrily exclaims, "Shit! What the hell was with all th' training?! Once again I'm staining my own hands with blood. God..." He thinks, "Once it's gone full-circle... where will it end?"
Basically, manga Wolfwood and Vash's beginning of their relationship starts with them forming a camaraderie before Wolfwood learns that he needs to kill/betray Vash. This makes it in a way more bittersweet, because their original interaction never had that tension of knowledge that Wolfwood is there since the beginning to betray Vash, and instead, they are simply existing together and form a what might tentatively be called a friendship--at least something where the both of them seem to have made a positive impact on the other-- outside of Wolfwoods mission. As a result, the question of how much of the camaraderie in the beginning of their relationship is Wolfwood having to get close to his mark is removed; you realize the camaraderie they share is honest and organic. In a way it's more tragic, because Vash even warns Wolfwood to remain away from Legato, but Wolfwood is already inevitably heading towards meeting the man, and learns to his horror that his next target is actually Vash. For Vash it also it's bitter because when Wolfwood finds Vash, Wolfwood mentions Knives for his reason of finding Vash; showing that even against Vash's warning, Wolfwood has clearly been entangled in some manner in the fight between Vash and Knives.
Anime adaptions
All this gets cut from Stampede, as Wolfwood is pretty explicitly following Vash to babysit him since the beginning. As Stampede has considerably condensed the story this makes sense since it would take time they don't have to add it in; but I think that cuts out an interesting extra dimension to Wolfwood and Vash's relationship, but so many things have been cut that I'm not surprised, and it's so changed that this being cut is not a big deal to me (compared to other things they cut which were more important).
From what I remember of the 98' anime, it's left a bit open to whether or not Wolfwood already knows from the beginning. However, as Wolfwood appears before Legato appears, it may mean that Wolfwood doesn't know during their first few meetings, like in the manga, but we aren't given a specific scene that shows Wolfwood being told to follow Vash, so we don't know where in the timeline he knows (we are only given the scene where he's told to kill Vash, later in the series). As well, Vash warning Wolfwood about Legato was removed in '98, which then lacks that bittersweetness of the realization that Wolfwood has become entangled in Vash and Knives fight. However, I haven't finished rewatching '98, so I don't have a more confident answer for whether or not Wolfwood knows, so take this part of the analysis with a grain of salt.
Conclusion
TLDR: In comparison to Wolfwood seeking out Vash to betray/observe him since the beginning, Wolfwood not knowing, (as shown by Legato not knowing who Wolfwood is when they meet) makes their whole first interaction in the manga organic, and adds a whole extra dimension of tragedy to their relationship, especially with the way Vash tries to warn Wolfwood away from Legato, which ultimately fails. As a result, the darker parts of both of their lives, which they don't acknowledge in their first meeting, end up intertwined, against their will. This actually serves as part of a huge thematic resolution of monstrousness and rejection but that's not the point here, that's another thing for another day.
Btw! If u wanna read more rambles from me, here's a masterpost of em :)
Edit (Apr. 2): Added photo ID, written by @princess-of-purple-prose
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