I have a 1966 RiddleBat question o/
Riddle me this, how do you think the two would describe eachother with/without the other present? Would it be the same or different :D?
That's a good question, and we can actually see examples on this IN the show itself! A lot of it boils down to hiding how much they respect each other lol
(Sorry this took so long to get to, my original plan was to re-watch everything with Riddler in it and analyise all their interactions, but the closer I watched, the more I realised it'd be more interesting to someday do in-depth analysises of each Riddler appearance, so we'll just be going over the major ones here).
We'll notice that for example Batman, wanting to stay in character in front of the criminal, will usually stay on path with the law, which usually comes in the form of authorative tones or criticism when he's particularly peeved at Riddler. We'll see him rattle off variations of "tricky devil"/"fiend" and comparing him to more stereotypically sly/evil animals, like "venal viper" and "rat" brought up a lot in the first episode (indicating Riddler listens to him, his very next scheme is teaming with The River Rats). He'll actively disapprove of Riddler's plans to his face, but will consistently praise his intellect when he's not around, intentional or not. Take S1E1, where he says Riddler has an "artistic compulsion" - he considers Riddler's riddles an art form. Or the countless amount of times something like this happens in which someone suggests something RIddler may be up to, and Batman will shut them down because obviously only he knows Riddler well enough to predict it, or simply talks as though he has him figured out:
Image 1 ("Hi Diddle Riddle", S1E01):
[Batman]: Not so fast, men, wait - the Riddler's up to something tricky. Better let us handle this - it smells like a trap.
Image 2 ("A Smack in the Middle", S1E02):
[Dick Grayson]: Got him, Bruce. The blast of that laughing gas, it must've got him.
[Bruce]: Who knows, Dick? The police never found a body. The prince of puzzlers may well have escaped underground...
Image 3 ("A Riddle a Day Keeps the Riddler Away", S1E11):
[Robin]: A chess king, the international chess tournament tonight! $25000 in prize money!
[Commissioner Gordon]: Boy Wonder, you've done it again!"
[Batman]: I think this thing is much bigger than that. The Riddler goes after millions, not thousands. He loves to dazzle us with his fancy footwork.
Image 4 ("A Riddle a Day Keeps the Riddler Away", S1E11):
[O'Hara]: Now we're getting somewhere! I'll have that place blocked so tight-
[Batman]: On the contrary. I think we should let the Riddler steal the tiara.
Image 5 ("A Riddle a Day Keeps the Riddler Away", S1E11):
[Batman]: A riddle a day keeps the Riddler away.
[Robin]: What?
[Batman]: Once, a long time ago, the Riddler made the mistake of telling me that. It means as long as he dishes out riddles, he's not finished with his plot. When the riddles stop, that's when he's ready for his final caper.
Image 6 ("The Ring of Wax", S1E23):
[Batman]:There's always some definite connection between the answers to his riddles and his nefarious plans.
There's many more examples than that, but you get the idea.
On the praise, we also get moments like this in S1E23:
[Batman]: If only the Riddler's inventive mind could be channelled for good... what a better world this would be.
Which is a really interesting one, because he really does not often wish reform to this extent on many criminals. He wants them to stop their ways, yes, but that's to restore order to Gotham City. In contrast, he genuinely believes Riddler could make a difference if he was good. He respects him.
On the same topic, he also tries to talk him out of things, which is also an interesting thing because he rarely tries to do this for anyone else; think Penguin or Joker, he generally criticises them, but doesn't try and appeal - notice in episodes like "Give 'Em the Axe", he will go for this angle with Riddler.
[Riddler]: And it's worth millions! Millions! Do you hear me, Batman?
[Batman]: Remember Riddler, you can't buy friends with money.
Really intriguing that he goes for the friends angle here. Combined with everything before about knowing him so well, it means he's thought a lot about what makes Riddler the way he is. And despite it all, the ego, the cool nature, the crime, Batman's come to the conclusion that Riddler is lonely. And wanting him to reform means he wants to be the person there for him. They both know each other better than anyone else, after all - think how many times they get perfectly equally matched by outwitting each other, or how Riddler can predict exactly what Batman is going to do. The surprise attack in S1E11. The entirity of most of his schemes relying on his knowledge of what Batman will do. Kidnapping Robin so often ebcause he knows it throws him off. Knowing he needs Robin to solve the riddles, tailoring them specifically to be easier for Batman when he's alone. Predicting it down to the exact time it will take Batman to do something:
"Batman's had time to solve the clue." (S1E1) // "Quickly, Moth, Batman's had time to solve my clue." (S1E23)
True, Batman tri,es to get characters like Newmar's Catwoman to reform, too, and this is for love interest reasons (though poorly-written ones; Stanley's episodes were... weird, and as such Newmar's doesn't come across as a very good Catwoman in comparison to Meriwether's and Kitt's who were better choices in my opinion), but even then it's never for that reason regarding change. Catwoman herself brings it up, but Batman never does. The belief he has in Riddler is on a higher level.
It's a constant battle of wits between the two, and they both respect each other to such a high extent despite it all. Take Riddler's monologue in S1E12: "So many people have tried. The Penguin, Mister Freeze, the Joker. All masters of their craft, granted… but I, only I, have triumphed in ridding Gotham City's criminal kingdom of the Dynamic Duo."
It's twisted toward his ego, yes. But if Batman wasn't a great threat, he wouldn't consider it such an achievement. It's exactly how Batman is - critical to each other's faces (though more teasing on Riddler's part), and praising whilst apart. They both mimic each other so well and their patterns are reflected in each other's behaviour. They're a direct contrast from each other, and they couldn't be without one or the other. When a henchmen mentions that with Batman dead, the other villains "will have no-one to outwit anymore", Riddler's face immediately falls - he won't either. And that's the real point of it. He loves the ego boosts, the attention, the riddles, the crime, but above all that, he loves outwitting Batman.
That one quote from the film confirms it:
[Riddler]: Oh, outwitting Batman is my sole delight, my joy, my heaven-on-Earth, my very... paradise!
Batman was right. Riddler is lonely.
And he wants his attention.
A lot of other versions of the Riddler are written to be obsessed with leaving riddles and have a genuine compulsion. That's not the case for 66 Riddler, which I have a better analysis on HERE. His "obsession" is Batman's attention.
Every other criminal has a similiar concept each time. Joker's goons are generally dressed the same, as are Penguins, Freeze's are always cold, etc., etc.. They have a constant. Riddler has something different every time, and even Frank Gorshin in an interview once said it was important for Riddler to always have a different approach.
His only constant is Batman. Batman is quite literally the closest thing to a friend he has besides maybe some of the other villains (most likely Joker & Sanders!Freeze).
Also whilst I'm here, Riddler canoniclly said Batman was handsome.
("The Ring of Wax", S1E23):
[Moth]: Aw, he looks so handsome beneath that mask.
[Riddler]: A diamondback rattlesnake is a handsome creature, too, but dangerous and deadly. Remember, Moth, Batman is our sworn enemy. We can ill afford such emotions as pity.
Handsome creature "too"? Okay, buddy, sure thing. And the talk about pity almost sounds like he's trying to remind himself. He doesn't regard her with eye contact when saying this, he just looks like he's thinking hard about something. But I'll get way more into these moments when I decide to do an episode-by-episode deep dive (please LMK if you guys would like to see that!).
In the 1979 special, both Batman and Riddler even say the exact same sentence in regards to Riddler's intellect: "If Shakespeare had had [my/The Riddler's] mind, there's no telling how far he would've gone!"
So, this was a lot, and that's all canon.
In an actual relationship? I do think he could eventually convince Riddler to reform (read: not do crime; a lot of his stances on things do not change) - I have many AUs on that, and Riddler would be clingy. He'd be dating Bruce "rather" than Batman, but he most definitely knows they're the same guy already, and would get sulky when he has to go to meetings, etc. Really good at flirting but absolutely awful because he won't shut up either outwardly or telling him in riddle form. Bruce would compliment him a lot on what he's doing well and just do an over all job to make him feel seen and special. If people didn't know they were dating, it'd soon become a suspicion just because Bruce would accidentally not be able to shut up about him, but not that Riddler minds.
After all, he likes the attention.
Thank you so much for reading all this and thanks for your patience in getting an answer! I hope this clarifies a few things lol, and please let me know if you want anythign elaborated on or have more questions! I love talking about this show and these idiots, thanks so much for the ask! <3
I don't know why this ship isn't more popular to be honest (specifically the 60s versions of them).