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First principles. Simplicity. What is at the core of any given character's identity?
If that character is Edward Nygma, the Riddler, then the one trait that's remained constant, throughout all of his many writers and years of existence, is that he wants to prove that he's the smartest person in any given room simply by virtue of entering it.
More than a few folks have accused me of this same trait, and there's probably more truth to it than I'd care to admit, so it's little wonder that I've always had time for the Riddler, in much the same way that thehefner has a soft spot for the Riddler's fellow Batman foe, Two-Face.
I was actually pleasantly surprised when DC decided to reform the Riddler, simply because it fit his concept that much better - after all, there's a limit to how smart you can consider yourself, when every scheme you hatch results in Batman forcing you to eat pavement - and I think his current status quo as a private detective is rich with untapped potential, but unless his new character concept gets utilized a bit more heavily by DC, I'm afraid that the character regression clock might already be counting down the moments before he gets turned back into a bad guy, because more traditionalist writers will start to feel like his reformation represents too much of a loss to Batman's rogues gallery to let it stand.
The problem is, the Riddler is a supporting character in a corner of the DC Universe where the primary character is already treated by canon as the world's greatest detective, so the Riddler can't just be the world's second greatest detective, or else his sense of vanity will steer him back onto the road toward villainy. As another detective, the Riddler really needs his own thing, not only to set him apart from Batman, but also to make him a worthy primary character in his own right.
So, Batman and the Riddler are both based out of Gotham City, but while Batman is an avenging figure who strikes fear into the hearts of criminals (and more than a few average citizens), let's let the Riddler build up a bit of a rep of his own among Gotham's overlooked underclasses - if you're a mostly decent person who nonetheless happens to be on the wrong side of the law, you might not necessarily want Batman to suddenly swoop in and solve your mysteries, for fear that he might decide to bring you to justice for your own transgressions, but fortunately for folks like you, Edward Nygma is here to help. He doesn't care about whatever crimes you may have committed, except out of curiosity, and he's willing to take your case for a very low fee, or maybe even for free, depending on how much it interests him, because the money is never really what's mattered to him - it's always been about showing off how smart he is.
So, Eddie's got a guaranteed clientele, and he might even have his office down by the docks to serve them better, since that's where so many such moody, atmospheric noir stories tend to take place anyway, but he's also got a built-in source of conflict - everyone outside of his client base hates him. The cops don't trust him because he's an ex-con with a rap sheet a mile long, so they're certainly not inclined to lend him any aid while he's working his cases. His fellow Gotham villains see him as a sell-out and a turncoat for going straight, and their regularly recurring responses range from hate mail and death threats to not-at-all-infrequent assassination attempts (this last one could even become a running gag). And Batman? Batman HATES the Riddler, now more than ever before. Batman hates the Riddler more for trying to be a GOOD guy than he EVER hated the Riddler back when he was still a BAD guy - not only because he distrusts the Riddler as much as the cops do, but also because there's enough of a selfish, greedy asshole inside of Batman that he doesn't like one of his former foes trying to show him up at his own gig, on his own turf.
Of course, Eddie does nothing to diminish this animosity. In fact, he deliberately fuels the fire of Batman's resentment, every chance he gets, because Eddie's more than a bit of an asshole himself. He had his choice of anywhere in the world to base his detective business out of, and yet, he chose Gotham, where more people know and hate him than anywhere else, and he did it to piss them all off, but Batman especially. Every time Eddie solves a case that Batman or the cops overlooked or dismissed or just plain weren't able to crack, he mails copies of the news stories to them, just to bait them. Again, Eddie's all about proving his smarts, and what better way than by not only surviving, but also succeeding, in the worst place possible? As for Batman, even though Eddie is reformed, he still wants Batman to hate him, because their feud has been going on for so long now that Batman's hatred actually feels like validation to him, to the point that he'll even leave false clues implicating himself for crimes that he didn't commit, just to prove himself innocent in the end, thereby proving Batman wrong in the process, as well as to draw Batman's attention and fuck with his head in the meantime.
If this doesn't sound very heroic, it's because the Riddler really isn't a hero yet, as much as he is an exceptionally competent asshole who just so happens to be doing the right thing for once. To my mind, this makes more sense from the standpoint of his character arc - after all, the guy used to be a GANG-LEADER (he had henchmen and everything!), so he's not just going to go from that to being a Captain Silver Age-style superhero, in terms of his morals. Even his switch to the side of the good guys is simply another way to feed his ego. At the same time, this is precisely what makes Eddie so dangerous to the bad guys' side now, because more than any morally righteous hero can, he knows how villains think from the inside. No, he was never on the same level as the Kingpin, or even the Penguin, but he was still a gang-leader, and how many guys that high up on the totem pole of organized crime make the switch to the good guys' side (and make it stick)? The Riddler knows all the mistakes that working-class bad guys make, whenever they try and pull off their capers, because he's already made all those same mistakes himself, and likewise, if there's any fracture-points to be found in a team of such bad guys, he'll be able to spot them. He's had enough experience that he can see which villains will have personality conflicts with each other, or which henchmen will fuck up or fold under pressure. He knows that sick, sinking feeling that seizes up in the pit of a would-be criminal mastermind's stomach, when they start to realize that their schemes are turning into a cascade of failure, and if he's facing down a bad guy, he will TAUNT them with that shit, just to psych them out and break down their nerves.
Along the way, he's going to grow a conscience, as he discovers, for the first time, that it can actually feel good to help people just because you know that you've made their lives better, but it's going to be a slow road to get to that point. In the meantime, he'll need some help, which is why I'd have him hire an assistant - a street-smart, working-class gal who needs a paycheck too much to complain about any halfway reputable job, but isn't too terribly impressed with Mr. Nygma to start out with, and becomes even less so once she realizes that he was the Riddler (at the risk of resorting to a cliche, I'm thinking that she or someone she cares about has been a victim of costumed crime in Gotham, and maybe she only took the job because it's the only way she can afford to put herself through law school). Over time, her barely tolerant disdain is transformed into amazement at the Riddler's mental ability, with a gradually building respect for the number of lives he's changed for the better. Yes, he'll still drop plenty of uncomfortable reminders about what sort of man he used to be ("Why would you expect them to commit their crime this way?" "Because that's how I would have done it."), but as time goes by ... yes, it's resorting to yet another cliche, but who knows? Even more than being his possible friend or love interest, though, she'll give him someone to show off his smarts to, and even serve as a point-of-view for the audience in those moments when the story requires the Riddler himself to act as a suspect or unreliable narrator (there should always be a tension about whether he might eventually "revert to type").
How would I open the first issue of the Riddler's solo series?
"So, you're Edward Nygma - the Riddler - and somebody actually hired YOU to investigate this case? You always left CLUES behind, when you committed your crimes!"
"Everybody leaves clues behind, officer. I was the only one who did so intentionally."
"Yeah, my point exactly! What would YOU know about catching crooks, when you're the guy who made it so EASY for people to catch you?"
"Even though I intentionally handicapped myself by leaving clues behind, my crimes were no more or less successful than those of any of my Gotham peers, so riddle me this, officer - what does THAT say about how much SMARTER I am than all the other crooks in this city, much less how much smarter I am than the COPS and the BAT who tried to catch me?"
Anyhow, those are my thoughts. And yours?
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I'm not sure you're quite right about the Riddler wanting to be the smartest man in the room - nearly but not quite. It's not about him wanting to be one-up, it's about him wanting to put the other guy one-down. It's about making the big guy look stupid. He's the kid in the class who pins the note on the back of the bully.
Dr Doom wants to be the smartest and has to prove it. The Riddler just wants to fool the smartest to show they have feet of clay. He's got "little man" syndrome even worse than the Penguin, except he doesn't want to climb on top of everyone else, he wants to trip everyone else down into the mud - a pratfall to prick the elite.
And let's not overlook that his need to riddle has been presented as a pathology. He wants the thrill of teasing the tiger. He wants the rush of "nearly got caught". It's a form of mental extreme sport.
Riddler as detective feels a bit wrong to me. The Riddler's not about SOLVING riddles as much as SETTING them. He's the DM, not the player. He constructs webs to tangle others, he doesn't venture into others' webs himself.
A "legit" Riddler solving crime does it by setting traps. He's the security consultant catching the Shadow Thief when STAR Labs gets targetted. He's the consultant Waller uses to snap the trap back the other way when HIVE's trying to infiltate Checkmate. He's the guy who sets up the scam to convince Luthor of Superman's secret identity being Hal Jordan. And in every single instance he's building in a chance for his adversary to get away if only they're really as good as advertised; he never believes they are.
I think the Riddler's not about the solutions, he's about the mysteries. He doesn't give the answers to his own riddles. Why would he give away answers toother people's puzzles? He might find them out for his own personal satisfaction but then he might just walk away and leave people wondering.
Finally, there's a big streak of childishness in the original conception of the Riddler. He's about "I have a secret". He's about "I know something you don't and I'm going to tease you with it". He's about "Nyah nyah can't catch me!" Maybe that's why in the oldest Riddler stories it's always Robin (Grayson) who's so good at decoding the Riddler's clues. That's not a criticism of the Riddler (after all, Joker is another villain whose earliest behaviour was slapstick childish) but it does mean that any really serious backstory for Ed Nygma has to tell us what made him like that.
IW
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