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Him and characters in the same trope of unrepentant assholes. Any tips in general would be great.

OOC communication is really important. You might play a dick ICly, but if you don't want people to hate playing with him (and by extension, you) you're going to need to be extra friendly and check in with people a lot. Maybe even a blanket permission post would be good.

That's definitely a given, yeah.

Unlike a lot of other unrepentant assholes in anime, Izaya isn't a genius. His strength lies in knowing more about the situation than anybody else and using that knowledge against others. We see him being a dick to people a lot in canon because that's what's required to move the story along -- but in reality, probably about 90% of his actual time is spent gathering information. You can decide whether he's actually conscious that he's not a super-thinktank or not, but a lot of the time he's not going to be able to be a dick by outwitting other people, and that's fine.

So his dickery actually lies in "I know something you don't", if I'm reading that correctly?

Yeah, but my point was actually that if you're going for someone who's going to be an unrepentant dick in all or even most of his interactions, Izaya may not be your best choice. Izaya in info-gathering mode is subtly parodic (see: Kanra) and passive-aggressive from time to time, but he only gets to be an asshole when he's completely on top of things and can afford to provoke a reaction. (Or if it's Shizuo, but that's its own bag of dicks, so to speak.) Especially in a new environment -- a game, say, where he knows nothing and has all these new humans to study (!111!!!) -- you'll likely find that Izaya's going to be playing around under helpful aliases more than he is under his own name.

Obviously he'll always be an asshole underneath and most of his CR would probably go sour within a few months if you took him to a game, but that's a bit more long-term than immediate "lololol your face/reaction".

Shinra, from the light novels, also describes what anon is elaborating on! Maybe it'll provide some insight:

"He'll appear like a ghost every time something happens, and act as if everything's happening in the exact way he has expected but he is actually as clueless as everyone else beforehand. Everything is obvious with the benefit of hindsight.

Just like those self-proclaimed prophets, all he does is talk about things that have already happened as if he had expected them long in advance. What's unusual about Orihara Izaya is that he can make such talks very convincing.

If you analyze his talks with a cool head, they probably won't be enough to take you in...but he'll always make sure to arrive on the scene at the best time and say the worst possible thing into your ear, so that you can't help but be unnerved." http://anni-fiesta.livejournal.com/40061.html

while i want to agree and say you can play it this way, this is not a god-given fact either. it's definitely implied that izaya has a very high IQ in the novels (he rarely makes mistakes, he learns languages as a hobby, he's been clever enough to work as an informant from age 17/18) and that may or may not mean he fits the term genius, but not being able to constantly outsmart people is not necessarily a sign to the contrary either even if i agree that he also may think he is much smarter than he actually is. or not. but my point is that these things are also interpretable and this opinion reads a little like doing otherwise would be doing it the wrong way.

that said, i do agree that he is more practical than to make an outright show of being a dick to people. it happens when it's warranted, which is actually also a sign of his intelligence. op's characterization of him as an "unrepentant asshole" is not wrong even if it is not always visible.

I should have been more specific. When I say 'genius', I mean actual genius, not "MENSA qualifier". So, Light Yagami-levels, capable of adapting and processing new information for use at high speed. Based on your examples, Izaya's intelligent and clever, but that doesn't mean he adapts quickly -- see the way he gets curbstomped the one time he tries extending his influence outside of Ikebukuro, and the reasons that led to his ultimate fate. He's quick in specialized fields when he puts his mind to it, but that's about all.

My advice was based on things that struck me as off in other Izayas in the past, which is a general tendency to focus on how ~ amazingly brilliant ~ he is and/or trollololololing along. I also threw in a note against playing him as an openly unrepentant asshole because, in my experience, when people ask for unrepentant asshole characters, they want someone they can play as rude, manipulative and bastardlike a lot more than Izaya tends to put out on a regular basis. I figured it was worth warning, because I've tagged one-note Izayas and they're tedious as hell.

OP: obviously any advice given to you should be taken with a grain of salt, but I still feel you'd have a hard sell for an Izaya who could rival the Death Note cast. Up to you.

Ah, no. No. If I wanted someone to play as rude and bastardlike... no. That's not my trope, just to get that point across. I did see him as the sort who doesn't really have any sense of being unrepentant for what he does but yeah, obviously any advice I'll take note of but that light novel link will be more of a bible.

Thanks you guys!

with this kind of character, it's always a good idea to app to a game that has something they'd get invested in, if only to try and completely fuck it over. you can really make use of the info-gathering trait here, and the ways he tends to do that, because if he's new to a "world" then there's a lot of stuff he'll want to know, and if he singles out particular people to study/manipulate, he'll want to know what drives them and their "contexts," so to speak.

izaya has a sharper, more practical intelligence, and very likely a good memory for small details about people. he's good at pretending to be nice and friendly (although even in canon some characters get a sense of something being a bit "off") to get at what he wants to know. very rarely is he outright a dick, or insulting, which is an unfortunate thing i've seen with a lot of izayas, and it just doesn't work.

also, he has the emotional maturity of the average seven year old.

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Izaya Orihara | Durarara!

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