I feel like there's something that goes unmentioned beneath the surface about the way Kendall is so much less charismatic than his siblings, than Connor who gets a fanbase all riled up after a few bad videos, or Roman who fucks around and finds out a lot of people are into that, or Siobhan who knows how to talk her way into just about any room long enough to get a foothold, and how it's so obviously because he doesn't know who he really is. Despite the fact all of them are plotting, scheming, little move-makers looking to simply climb another rung in the ladder, Kendall's almost always literally clawing his way into the same places his siblings got without having to flex those muscles at all, despite having the most advantages. The other three use their natural abilities, their personal charms, their inherent tricks that come easy, and Kendall always seems to be playing catchup in that field. He's all sweaty hands and awkward pauses, waiting to see if what he just said, what he just did, actually hit its mark at all.
There's so much distinctive personality between Connor, Roman, and Siobhan that they never back off of, never second guess, never change in the moment to try and appease a crowd, and yet that seems to be all Kendall ever does. He's constantly trying to be something he's not, constantly trying to meet a standard, hit a mark, sell a look - fit. His oscillation between identities is unlike anyone else in the show, it's frenetic and disjointed, an up-down of artsy sneakers he kicks off within minutes of perceived judgement and glitter-cast UFO jackets he, ironically, wears whilst saying he doesn't want to look like an asshole, in a tone that sounds so disappointed in himself - Because he is.
Connor is okay with being niche, with being the odd-one-out of the company life, with living in a world that none of his family understand or really want to at all, and when somebody pushes him on it he doesn't try to rework it for them to view as respectable because it's what he wants. Roman is okay with being the sick puppy, with being detestable but endearing in a slightly unsettling way, with living a life that directly offsets his own views, and when somebody insults him for it he just doubles down because who gives a fuck? Siobhan is okay with being the black sheep of her family, with being the one who's views and identity don't quite fit the Royco way, with constantly butting heads about the slightest difference in words even when she gets laughed at, and when somebody pushes her on it she stands her ground because she believes she's right, or at least deserves the space to argue that. Kendall, though? Kendall is not okay with any of those things being applied to him, and when pushed on almost any aspect of his identity that is viewed as a flaw, or a fault, or a weakness in his character, he does just about everything in his power to "correct" it. Even his pure beliefs get diluted beneath this slanted view of other's perception, like his genuine belief that women shouldn't be pressured into precarious positions by their bosses gets diluted beneath the fear that he'll be perceived as one such boss to the point he directly contradicts the woman's wishes and puts her job in danger to try and save face, or his belief that lackluster pushback against his corporation's neo-Nazi news anchors and sanctioned presidential candidates is a dangerous slope in threatening the lives of many, including his own family, gets diluted beneath the fear that he'll be seen as a weak businessman if he doesn't go ahead and sign off on that sanction anyways. He can not find his natural charisma or charm, his innate likability, because he's too busy clawing it up at the root any time it gets questioned by those trying to keep him down. His attempts to perfect his personality, his identity, his innate state of being, is exactly where he fails. It's an impossible task. So much of his charm, to me, comes specifically from his flaws and those little glimpses of how he actually feels, who he actually is, what he actually wants ... But, instead, most of the time he simply comes across as being unable to be anything at all, because he's too focused on perfecting something that can never be perfect.
Even cousin Greg with his awkward, people pleasing little misquote-esque behavior isn't as fragile in his identity as Kendall. He manages to make it through the whole show without ever changing who he is at the core or masquerading as someone else, he's always got that distinctive awkward demeanor and those naive tendencies, even when he's fucking people over, that not only give him an up on the competition but make him appealing in a way that, again, Kendall doesn't seem to be. This goes for Tom too, who manages to not only be rather liked and respected by Logan near the end of his life, but who also goes on to get the entire company, despite never really changing the fundamentals of his identity. Everyone in this show sacrifices certain aspects of themselves, or their dignity, for what they want, precisely because that is what this world requires, but Kendall's constant shapeshifting is so clearly different ... It's personal. Siobhan believing she's a feminist, and a liberal, and a forward thinking modern woman, whilst simultaneously fighting tooth and nail to be the face of Neo-Nazi News And Sex Abuse Cruises (TM) is an example of her imperfection, of her acceptance of that hypocrisy, whereas Kendall's belief that he's also forward thinking and an example of a safe "fuck the patriarchy" type of guy crumbles, in his own mind, when he's actually critiqued on it, or pushed on it, or asked to step away from it, because he knows he's directly contradicting himself and giving that up. Siobhan has no problem being both, she can work it, she can say one thing and be another, but Kendall can't because Kendall's giving up one or the other and he knows it. It's why they're juxtaposed across the table as the numbers roll in. It's why he's the one always looking for someone to tell him he's good. It's why he asks her. He wants to be good. He's not, and he can't be, but he wants it so badly. He wants to be good, but more than that he wants to be perfect, and despite the way they should, they don't actually coexist within the world he lives in.
