You'd think that as a combination OCD-haver/comics blogger I would have more interest in The Riddler as possibly the most popular obsessive-compulsive or at least OCD-coded character in cape comics but for some reason it's never quite captivated me that much -- which is weird, because especially growing up, I did always love The Riddler a lot. I do think that when writers lean into the why and the must of leaving riddles, it does a significant amount of heavy lifting to get him out of the "discount Joker" role he can occasionally fall into. Furthermore, it's a lot more interesting than arrogance plain and simple -- like, Eddie can be arrogant, but so are a lot of characters and not all of them have to leave riddles specifically to prove their point of superiority (and I think some writers have tried to write the Riddler with a comic book writer's understanding of a narcissistic personality disorder, but let's stay on topic).
I think that where a lot of "The Riddler has OCD" writing loses me is that they only go one layer into it. The Riddler is obsessed with riddles so he has to leave riddles to his crimes or else he loses it, and he's obsessed with riddles because he has childhood trauma from his dad not thinking he was smart enough as a kid or whatever. There's a couple different origins kicking around but I haven't read any Riddler comics that make it particularly compelling.
But that's the thing, isn't it? OCD in my experience doesn't have a particularly compelling origin story in someone's life, usually. It creeps up on you before you even know it's there. It's some kind of specific discomfort that you find a specific way to alleviate, and that pattern entrenches itself in your brain through repetition until all of a sudden you'll go insane if you don't do your Special Thing. But OCD feasts on pattern recognition and personal significance. So it's only in retrospect that you eventually sit back and think, ah, of course, this is when I developed my obsession and compulsion, this is how it affects me, clearly. It's only in retrospect that you solve the riddle.
And that's what I want to get at. The Riddler, to me, shouldn't be a character obsessed with riddles, he should be a character obsessed with answers. He should be a character so discomforted by the uncertainty of the world around him, of the falseness of meritocracy (and the very high place that he is so sure he should have in it), of the complete lack of control that he actually has, that he is compelled to force certainty, truth, and control in every place possible. Every scenario, every situation, every interaction is a puzzle with a clear and fair solution -- he just has to find it. In this sense, I don't think that the riddles he leaves for Batman or other heroes should be the compulsion in and of itself. I do think he does it to be arrogant, but I do think he also does it because that is how he sees everything he already does, whether it's a criminal caper or not -- as a riddle to be solved, and as a solution that should be rewarded. He's giving those pursuing him the same game that he's constantly playing himself but on what he believes is a much lower difficulty. To bring up the Joker comparison again, if the Joker is the, yknow, "chaos guy," chaos of any kind should make Eddie so nervous and sick that he wants to throw up and shit himself. He needs everything to be in order because he solved for this. He solved for this because the only way that he couldn't have solved for this would be if there's no actual perfect solution at all, and that just can't be true. It can't. (in this way, he's someone who probably thinks of himself as a logistics expert, a la Clock King, but he's actually far too unwilling to accept unpredictability for what it is to truly excel at that line of thinking.
But unfortunately, a guy who writes brainteasers for the world's greatest detective is already difficult enough to write stories for when his character is reduced to having a hissy-fit if Batman beats his little challenge. I think this is why I like those stories or those eras where the Riddler isn't a villain and is doing P.I. work or other brainy stuff besides crime, because without the leash of needing to leave calling cards, you're forced to explore what actually makes him "The Riddler" in a much more vulnerable way -- a writer would, ideally, show how this shit affects him in other tasks in daily life. If he's really got obsessive-compulsive disorder and not just an affinity for riddles, then he's not the kind of guy who "clocks out" of thinking things through this way!
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