You can consider this as my Riddler tribute.
A lot of Batman's enemies either were more combat or mental theme with Bane representing both very well. I strongly felt none of the mental villains represented the theme more perfectly than The Riddler. Obviously among Batman's smartest enemies. Possibly the most mysterious than The Joker which is quite an achievement.
I know to some people they see the character being more of a joke. To be honest it's not difficult to see why either. He often wears green outfits with question marks. He leaves behinds riddles for Batman to solve like some sick game. Also some of his famous portrayals are more comical. He's among the worst combatants among his regular enemies as well.
Personally I always enjoyed Jim Carrey & Frank Gorshin performances myself. Paul Dano went into a rather unique direction with the character in The Batman movie. The live action Batman movie not the cartoon show of the same name. Which also had it's own movie that had Dracula. I also enjoyed Cory Michael Smith as the character on Gotham show too.
I also enjoyed Batman: The Enemy Within Riddler too. I just wished he was more into the game. Although it still was a great Batman game. Over the years, there's a lot of interesting variations of the character. We seen him being a much lighter character to an incredibly dark one. Somehow, people has so many ideas what to do with him.
The Riddler often kidnaps people to force into death traps. This forces Batman to go search to rescue em. He's always been great with technology rivaling Batman to a degree. Regardless which Batman story, he's always a difficult character to predict. You just never know what scheme he's about to unleash onto Gotham City.
He's also among the most realistic of his enemies too. I wouldn't be surprised there were people like The Riddler exists in the world. What I love so much about the character is he simply creative with his unique skill set. You never know if he's keeping an close eye on you or not. He's so obsessed trying to out wit Batman, he often loses over that arrogance of his.
Everyone knows The Joker always been Batman's arch enemy. But I have seen some rather convincing arguments why some of his other villains fits the bill more than The Joker. I actually had a friend that believed Bane was his nemesis. To be fair, Bane is a great choice challenging the dark knight beyond most of his enemies.
Some could also argue how it should be The Scarecrow. Whose actually my second Batman villain. In some aspects he does more directly come off as being the chaos to Batman's order. Yes I know that's what Batman/Joker should to represent as well. The Scarecrow does go big on causing chaos with his specialty fear toxin.
The Riddler could match Batman's intelligence. Batman among the smartest in the Justice League. Like Batman, The Riddler can be quite resourceful when he needs to be. His unique skill set already makes him more dangerous than most of his enemies. He often operates in the shadows. In order to take surprising opportunities away from other notable villains.
On the surface, he seems like an easy character to figure out or simply not take seriously at all. Deep beneath the surface, we got a truly in depth character. His obsession trying to out wit Batman became a major drive behind many schemes. He's always coming up plans b to z on the fly. Things are never simple with The Riddler.
Not only that, he easily could cause hell without having to directly get his hands dirty. Characters like Jigsaw in Saw series are inspired by The Riddler. He always had a unique perspective of things with some being incredibly deep. Some of which you really gotta take time to think about. The Riddler is secretly among the scariest Batman villains.
Some of his big enemies like Two Face or The Penguin. Batman has ways to know things from their henchmen or some business partners. Usually forcing that information out of them not quite The Punisher style but close enough. Also there's more obvious signs they are involve. The Riddler easily could not left any riddles behind to cause more confusion.
The other major reason he lefts em behind is simply buy himself time to continue his plans. He knows most people in Gotham aren't as intelligent as him and Batman respectively. He's actually smart enough to carefully make it appear as if another major Batman villain done it. Which is kinda scary to think about.
Not even The Joker would do that. The Joker is willing to do virtually anything horrific to get what he wants. The Riddler doesn't want chaos but rather his view of order. He already knows the corruption Gotham had for years. He simply believes anything he's doing is for a greater cause. Which kinda makes him a little similar to Ra's al Ghul in a few areas.
Whose got some of The Riddler's skill set. Now throw in being an legendary assassin that commands most assassins in the world. Plus having connections with powerful people. We got a man who could easily claim a lot of the world. Now what if The Riddler somehow forced him over Ra's al Ghul. In a way he couldn't be killed?
I'm talking about what if The Riddler had a deal with him. Basically if he does several things. Ra's al Ghul must give his word assassins won't attempt to kill him. Of course, you can't trust either of these villains. The Riddler can easily black mail some powerful people. Just as easily to go off grid while hiding from Batman.
Sometimes you just never know how truly involve The Riddler truly is in things. Batman: Arkham series is a great example of this. He operates in the shadows while aware of everything going on with Batman. At the same time, he couldn't resist giving Batman a lot of riddles to solve. The Riddler is a character that's quite complex that nearly everyone has their own unique take of the character.
What also makes him terrifying to have as an enemy? Sometimes people close to you either willing or being forced are working for The Riddler. The fact he operates in the shadows this well. You can't simply trust anyone knowing he's involved in some way. This goes to show how determine he truly is. He often prefers to avoid confliction with The Joker for many reasons.
Virtually no where is truly safe when he's around. What might appear as people rampaging might be more going on than you think. You could even be his best friend, he still could force you into doing something horrible or kill you. In other words, you simply have to do whatever he tells you or die. Now to be fair, this is technically better than a lot of Batman villains.
For example, if it were Two Face. He simply flips a two sided coin into the air. You better hope the unscratched side lands upwards. The Penguin wouldn't waste time killing em either. The Joker could either kill you on the spot or force you into a trap that's not pleasant. The Scarecrow likely gas you causing fear that could kill you too.
The Riddler has a little humanity unlike most of his enemies. This doesn't mean he won't do such things to people, you bet he has before. He's a man that wants to be rememberable for his greatness. There's no question he brings creativity to his line of work. He greatly makes up for not being a good fighter. For him, he rather test people mentally to truly see who they are.
Therefore, he lacks interest in actual combat. He prefers doing twisted games as well as leaving riddles. He also tests Batman's determination a lot. There's no sugar coating it, he's a major pain in the buttlocks for the dark knight. The Riddler is a character that embodies a gifted person going to the dark side. But doesn't fully lose his sanity in the process.
There's plenty proof he remains some of his sanity. He's actually among the most sane Batman villains. Despite all the stuff he's done over the years. He's a master strategist that always has tricks up his sleeve. He wants to put on a great show. At the same time, his own arrogance usually the main reason he loses to Batman often.
In my mind, The Riddler truly deserves respect among the Batman villains. Eventually I may do another Batman villain I loved a lot as well. For the present, this felt long overdue. The Riddler is a great Batman villain that tests Batman mentally unlike most of his enemies. The world simply isn't the same without him, it might become boring.
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