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Riddle Me This: what’s black and green and purple all over? Answer: very obviously, the Riddler! (Not really a riddle, just simply a description...so sue me.)
After making my list of the Top 10 Mad Hatter Comics, I decided that I enjoyed doing that list so much, why not make a couple more lists devoted to my favorite comic stories involving my favorite Bat-Rogues? So that’s exactly what I’m going to do. The Riddler seemed a good place to start because...well, he’s an interesting case. The character is very well-known, and undeniably one of Batman’s most infamous Rogues...but a lot of people seem split on him. ESPECIALLY in terms of his appearances in the comics. Much like with the Mad Hatter, so much of the good stuff we get out of the Riddler comes not from the comics themselves, but from other media, such as television and video games. However, there are some truly great Riddler stories out there, and they deserve to be recognized. So, let’s waste no more time! Slap on a domino mask and prepare to quiz, quip, and query anything you like: these are My Top 10 Favorite Riddler Stories!

10. Crime’s Puzzle Contest.
Published in Detective Comics #142, 1948. Written by Bill Finger. This was actually the Riddler’s second appearance, after he seemingly drowned in his first. (More on that story later.) Popping up alive and well, the Riddler stumbles upon a “National Puzzle Club,” where an awards ceremony is being given. Being the Riddler, he steals the most coveted award, and flees. However, the idea of a puzzle club and/or contest has given Edward Nygma a fantastic idea: what if he stages a Gotham-wide puzzle contest, leaving riddles and puzzling clues where the entire populace can see? The catch, of course, is the prize: every clue leads to his next caper. It’s basically the Riddler doing what he always does, but on a much grander scale than in some other stories. The idea of Edward Nygma deciding to put on a big contest is also pretty fascinating; on the one hand, it fits in with his ego - he lights up billboards, hacks electronic signs, etc. Everyone’s eyes are on him, and everyone’s left wondering. A need for attention and respect is a big part of Riddler’s character, and always has been, so a story like this works well. But the best part is that it works to his advantage both ways: for example, when Batman & Robin inevitably solve one of his clues, Riddler is able to escape into the massive build-up of cars that have come about due to everyone rushing to try and solve his puzzle. He’s not intentionally using the clues as a distraction, so much as he is taking advantage of the times they do. It’s a clever ploy for the character, all around, and leaves us with a very good, and rather underrated, little comeback story.

9. Remarkable Ruse of the Riddler.
Published in Batman #171, 1965. Written by Gardner Fox. What’s MOST fascinating about this story actually is not the story itself: it’s what later became of it. Because less than a year after this story was published, the famous 1960s Batman series - with Adam West as Batman, and Frank Gorshin as Riddler - first aired. And what story did the creators choose to adapt for their first episode? This very one! Now, admittedly, there are MANY differences between the television episode and this comic (as was the case with a lot of the stories directly based or inspired by comics for the show), so that hardly makes the story itself great on its own...but the story IS very good. After a long hiatus (almost twenty years in the real world, in fact), the Riddler comes back to Gotham City, claiming he is ready to turn over a new leaf. (Spoiler alert: he really isn’t.) For his first act - and in a sequence that wasn’t in the T.V. episode - he actually HELPS Batman & Robin capture a bunch of thieving crooks! From this point on, the Dynamic Duo don’t know what to believe - as time goes on, the Riddler seems to be doing some sort of dastardly deed or another, but each time Batman & Robin get close to catching him, they find themselves foiled as its revealed that the Riddler was doing nothing wrong at all. It doesn’t help that Nygma has apparently inherited a large amount of money from his uncle, which often becomes a major issue. In one famous scene, they believe they catch Riddler stealing a jeweled cross from a man at gunpoint...only to find out that the “gun” was actually a novelty cigarette lighter that resembled one, and Riddler had just purchased the cross. He was just giving his “victim” a light! Aside from its connection to the 60s show, it also makes for another great comeback story...again, especially considering, at this time, the character hadn’t been seen in decades. And, once again, it actually does give you a surprising little look into Riddler’s mind: again, he has inherited a large amount of money in this story. But what does he use it for? Taunting Batman & Robin! It really goes to show you that Nygma doesn’t really care about money. Oh, he’s glad to have it, and he finds all sorts of ways to use it, but the ultimate goal is just using it as a little extra something to dangle over the Caped Crusader’s head. The comic also features one of the most famous Riddler covers of all time (pictured above); this is from another scene that didn’t make it into the show, and exactly what’s happening there isn’t revealed until near the end of the story...but it’s a fine bit of silliness when this strange image we’ve been wondering about finally comes into play. It keeps you going, making you wonder just what’s going on and why, which is what a good, eye-catching image should do. For all these reasons, this story definitely deserves some recognition.

8. Solitaire.
And now, for something much more recent. This was part of the New 52 continuity, published in Batman 23.2, 2013. Written by Ray Fawkes & Scott Snyder. Now, let’s talk about the New 52 for just a second: this was an attempt by DC to try and “reboot” many of their famous characters and universes for a new generation. It was...controversial, to say the least. Many fans felt angered by the changes, especially since not EVERYTHING got totally changed, making the timelines more confusing rather than less. And what things were changed, not everyone felt were changed for the better. And, yeah, the New 52 struck out several times - such as the stupidity of “Death of the Family” (sorry if you like that story arc, but I do not...AT ALL), or the mediocrity of “Mad” (the Hatter’s big story arc) - but when it got something right? By God, did it get something right! And the Riddler was a prime example of that. In this story, the Riddler breaks into Wayne Enterprises HQ to get revenge on a guard who abused him back at Arkham Asylum. You see, in Arkham, there was/is a strict “no games or puzzles” rule for Nygma, apparently, and this guard used that to his advantage, not even allowing the Count of Conundrums to play a peaceful game of solitaire. There’s a twist to Nygma’s plot, however, which connects to an overaching storyline...but I mustn’t say more there, or I’ll spoil the surprise. There are so many reasons this story is great. First of all, it really does let us see the Riddler for what many people sometimes forget he is: a genius and a threat. Nygma isn’t just leaving crazy clues all over the place, he’s breaking into one of Gotham’s most secure buildings, and taking out anyone who tries to disrupt his scheme in even the slightest way, and he’s doing it EASILY. The panic of so many of the other characters in the story - such as the former Arkham guard who now works as a security man for Wayne, and the various employees and other security personnel who are there - are contrasted by Nygma. Through the majority of the story, he is calm, poised, and surprisingly quiet. There is, however, one point where the calm is broken: an indignant woman, trying to make a stand, punches the Riddler in the face. His reaction? He starts beating her with his cane, and then shocking her with powerful electrical charges, raving all the while, saying things like, “YOU DO NOT TOUCH ME!” and “You have to know what you are.” It’s clear to us that the Riddler needs one thing perhaps even more than attention: he needs respect, and more importantly (at least in this story), he needs a sense of control. He cannot accept that anything or anyone can “touch him,” figuratively or literally, so when the control is apparently broken, he lashes out. And if anything or anyone besides his intended target is in the way? Either they stand aside, or they get trampled underfoot. Nygma almost feels like a force of nature in this story...which makes the calm and slick twist at the end of the tale all the more interesting. For giving us Riddler at both his most dominant, and his most vulnerable, all at the same time, this story definitely gets a place on the list.

7. The Riddler.
Published in Detective Comics #140, 1948. Written once again by the great Bill Finger. This (as the title may imply) was the character’s first appearance. The thing about the first appearances of many Batman Rogues in the comics is that they tend to be hit or miss - for example, Joker and Penguin came out practically as fully formed characters, but some other villains (such as Scarecrow and Poison Ivy) took time to develop into the characters we know today. The Riddler, thankfully, came out as one of the former. The story gave us the first take on his origin story (which has not so much “changed” so much as simply been expanded upon over time), and provided some of the most famous traps and clues the character would ever use. This was also another story to inspire an episode of the 60s show; this time, it was John Astin’s two-parter as the Riddler, although, once again, there would be a lot of changes from the source material. There’s not much to say about the plot, mind you - basically, Edward Nygma, a man obsessed with puzzles, word games, and riddles, decides he needs greater intellectual challenges in life. So, he decides to commit puzzle-themed crimes, and leave clues to the police (and more importantly, the famous Batman) to try and solve, just to prove how clever he truly is. The traps themselves are delightfully elaborate, the riddles fun, and for a story from the late Golden Age/early Silver Age, it can actually get pretty brutal: for example, the Riddler cages a man in an elaborate trap that will slowly suffocate him as time goes on, and might even crush him to death. The Dynamic Duo have to figure out how to unlock the puzzle cage before the man is utterly destroyed. But, in keeping with the Riddler, neither money nor random death is really what he’s after: he simply wants to create the perfect puzzle, find the perfect mental match, and he sees Batman as his way to accomplishing these goals. It’s a simple introduction, but also a beautiful one.

6. A New Dawn.
Published in Batman Confidential #26 - 28, 2009. Written by Nunzio DeFilipis & Christina Weir. This three-part story arc is most well-known for introducing the character of King Tut, one of the most famous original villains from the silly 60s T.V. show, into mainstream comics. Much like the original, Tut is a man who believes he is the reincarnation of the great pharoah Tutankhamun, nicknamed “King Tut” in popular culture. The big difference is that he is a serial killer, who tells ancient riddles from old Egyptian texts to warn his future victims of their fate. Tut himself, however, is not so much the focus as the REAL conflict of the story: in order to stop this new, riddling menace, Batman is forced to team-up with the Riddler. “I think in riddles,” Nygma argues, reasoning that no one is better to face such a foe, and making it clear his reason for wanting to help is simply “professional pride.” No one is going to more or less steal HIS modus operandi and get away with it. (...Which makes you wonder why he never bothered the Cluemaster or the Puzzler, but whatever; maybe they have a truce of some kind…) What’s most interesting about this story is the way Riddler is portrayed; he’s funny and eccentric, and never really outright threatening...but at the same time, neither we nor Batman himself are ever sure how much we can trust him. The story is also a great showcase for Riddler’s own mind; for a character who is supposed to be Batman’s intellectual equal, many stories seem to forget this, and depict him as something of a fool - a madman who THINKS he’s brilliant, and doesn’t realize his own self-destructive issues. In this story, Riddler actually tends to figure things out before Batman does, and is actually able to use the fact he ISN’T trusted to the situation’s advantage. He’s cunning, he’s manipulative, he’s tricky, he’s snarky and strange...but at the end of the day, and here’s the clincher: he actually DOES help, and not only that, he doesn’t turn right around and try to cause trouble himself. It’s a bizarre little story, introducing a bizarre sort of villain, with a bizarre team-up to top it all off, and one of the most complex and clever portrayals of Riddler you’ll ever find. I ask you, ladies and gents, what’s not to love?

5. Dark Knight, Dark City.
This three-part story arc seems forgotten by a lot of people, which is a shame. It was published between Batman #452 - 454, in 1990, and written by Peter Milligan. The tale focuses on the Riddler concocting another crime spree...but something is very...different this time. The Riddler behaves more maniacally, psychotically, and downright sadistically than ever before. As one of his own goons points out, “You’re making the Joker look downright sensible!” He hangs people, sets off bombs, and even endangers innocent babies in a variety of rather disturbing ways, to say nothing of the horribly treacherous way he treats his henchmen. But here’s the thing: everyone in the story, in some way or another, acknowledges this is NOT normal for him. The Riddler, after all, while not a villain who will shy away from endangering people or spilling blood, doesn’t actively SEEK IT OUT. His schemes are focused on proving his wits, gaining respect and adoration...not senseless violence or brutal slaughter. As the story goes on, it becomes clearer and clearer that something isn’t quite right, and that perhaps Edward Nygma isn’t totally in control of what’s happening. This story, in some ways, sort of reminds me of “The Mad Hatter Flips His Lids!,” one of my favorite Mad Hatter stories: it starts off more or less like a Gold or Silver age story, but in this case, it proves that under the right circumstances, a villain from that age can cause a lot of problems. The difference is that, much like with another Mad Hatter story, “The Wonderland Gang,” this reckless cruelty is NOT the way that villain usually behaves. It ends up becoming less of a classic superhero tale, and more like a Gothic horror story; think H.P. Lovecraft meets...well...Batman. And as someone who loves that genre...well, how can I not give this tale a place high up on this list?

4. E. Nigma, Consulting Detective.
Also sometimes titled “E. Nygma, Consulting Detective.” Published in Detective Comics #822, 2006. Written by none other than the amazing Paul Dini. This was actually one of the first stories in a many-issues-long run with stories all written by Dini: one of the chief creators of the DCAU, and widely considered to be one of the best Batman writers of all time. ESPECIALLY when it comes to the villains. In this story, the Riddler is released from Arkham, and declares that he’s giving up crime in favor of being a crimefighter himself. With his usual flair, he announces he plans to become a private detective! And...he actually means it! He really does want to turn over a new leaf and try his hand at stopping crimes rather than committing them. He’s not doing it necessarily out of the goodness of his heart, since his motivations are more or less the same, but he’s still trying his hardest to give up all the old, villainous habits. Nygma’s new career actually lasted for quite some time (not TOO long, though), and this was just the first story where he began his new job. But, for me, it’s also the best one. In some ways, this story is a lot like “New Dawn”: the Riddler and Batman have to team-up to catch a criminal, and hijinks ensue. The difference, however, is that Riddler is totally sincere about his plans to go straight, and as a result, the rivalry between he and Batman feels all the more humorous. Not only is Batman constantly trying to prove the Riddler is up to no good, both of them are constantly trying to one-up the other. Heck, the only reason Batman ends up solving the case before Nygma (and no, I don’t think that’s a spoiler, let’s all be honest) is because he decided to he just couldn’t let Riddler WIN. He HAD to prove the man wasn’t right. In a way, this almost makes Batman seem as bad as Riddler himself can be. You really do see why the two are such strong equals, and that Batman really does have competition in the form of his old enemy. And because Riddler IS sincerely trying to go straight, you do feel a bit bad for him when he loses; yeah, he’ll have other cases in the future, and yeah, he was sort of an arrogant git...but he’s trying his hardest, and he has to live with the knowledge that his first real case was solved by somebody else. For someone already obsessed with proving themselves the better brain, that’s a tough blow to take, and it haunts Nygma throughout the rest of his time on the job in future stories. Again, “Detective Riddler” would appear in other stories by Dini to come, but this first try of his will always remain the best in my book.

3. Batman: Zero Year.
Published between Batman #21 - 27/29 - 33, between 2013 and 2014 (part of the New 52 continuity). Written by Scott Snyder & James Tynion IV. As I said before, when the New 52 did something right, they did it VERY right. For many, the massive story arc known as “Zero Year” was almost undeniably the best Riddler story to appear in recent years...indeed, some have gone so far as to say it’s the best ever written, period. And, yes, it definitely is one of the Greatest Riddler Stories Ever Told in my book, too. “Zero Year” was a new retelling of Batman’s origins, and his first foray with supervillains in Gotham. Nothing new there, and the story has its ups and downs (more ups than downs, thankfully). But what people loved the most about it was the Riddler. Not only are his origins pretty good, and not only does he play a HUGE role in the events of the arc (in fact, for the last third at least, he’s the main villain), but this was probably the character's BIGGEST story. Because the Riddler succeeds in doing something few other villains have acheived: he all but CONQUERS GOTHAM CITY. I like to call this story “The Dark Knight of Riddler Stories;” it really is very similar, in a lot of ways. Batman is relatively new to his newfound “job,” and he runs into a villain unlike any he’s ever faced before. Someone who can out-think him, someone who is nigh-untouchable, and someone who has just as much of a sense of theatricality as he does. Anyone who says the Riddler is a “wimpy” or “silly” villain should definitely read this arc; they won’t be thinking that for long.

2. The Riddle-less Robberies of the Riddler.
Published in Batman #179, 1966. (Yep, same year the Adam West show went on the air. Yet they never adapted this story...weird…) Written by Robert Kanigher. This story is unique for many reasons: the biggest one being it’s actually rather ahead of its time. If you look at the Silver Age and its villains, while they certainly had their fair share of fun stories, most of the villains then WERE NOT ACTUALLY outright insane. In fact, most of them were not even that threatening. The Comics Code of the time just didn’t allow for a lot of meat on the bones, so to speak, and kids - the primary demographic - were fine with just a bunch of crazy, nonsensical adventures, and parents were cool with it as long as their kids didn’t try anything too crazy in response. So THIS story HAD to make an impact...because it comes right out and calls the Riddler crazy, and actually, in a surprisingly short amount of time, manages to provide a fascinating little character study. The Riddler decides that he’s tired of his self-destructive riddles getting him caught, so he decides he’s going to commit a series of robberies and leave no clues or intriguing puzzles at all. Sounds fair enough. The only problem is that he can’t seem to do it. He feels he HAS to leave a riddle, make up a trap, do SOMETHING other than just take the stuff and go. Realizing he has a problem, he takes some self-help courses to help control his urges...but when he finally does get back into the crime game, he’s left with the ultimate riddle: can he truly commit a crime without any gimmicks? Having a villain cope with their own mental issues, and still making it a fun story kids could understand, and actually making it a real mystery to top it off (read the story to see what I mean there), were actually really groundbreaking ideas for a Silver Age story. It doesn’t help that this was, believe it or not, only the FOURTH TIME Riddler had even appeared in the comics. He wasn’t the infamous Rogue we all know him for today; he was just a minor maniac in a great tapestry of villainy. I am convinced that this story and Gorshin’s work on the television show that came out at the same time are jointly responsible for why the character became so much more popular in later years; we never really got to see a good view of how JOKER’S mind worked, or Penguin’s, or Catwoman’s. Even today, the idea of the Riddler having to try and keep his compulsions under control is still fascinating, making this old time classic just as good a read nowadays as it ever was.

But as fascinating as “The Riddle-less Robberies of the Riddler” is, there’s one story that’s even better...

1. Questions Multiply the Mystery.
Published in Detective Comics Annual #8, in 1995. Written by Chuck Dixon. In this story, Riddler gives us a self-narrated new take on his origins, going from childhood traumas to modern complications. This is a very simple set-up, but the story, itself, is anything but simple. There has never been a more in-depth look at who the Riddler is and why he does what he does than this comic. Everything from his feelings about Batman, to his reasons for loving puzzles, to his relationship with Echo & Query (his most well-known henchgirls from the comics...actually, perhaps ironically, this is the only story in the top ten where they appear), and so much more is covered here. The origin story itself is really good, too. Nygma’s fears of being forgotten, unnoticed, unloved, etc. are all laid bare. But the ultimate twist is this: he HATES telling us all of it. A riddle is only interesting when you don’t know the answer. So what does that make the Riddler when everyone knows his deepest and darkest secrets? As much as he loves to play to the crowd and flaunt his abilities, there are some things he cannot stand to share...but for reasons we’re not wholly sure of until the very end, he can’t stop himself from telling us every last detail. And the twist about what’s really going on that comes in at the end is simply breathtaking. What more do I need to say? For reasons as obvious as why the chicken crossed the road, “Questions Multiply the Mystery” is undeniably the Greatest Riddler Story of All Time.

Honorable Mentions Include...
The Oldest One in the Book.
Part of “Batman: Gotham Adventures,” a spin-off series based on “The New Batman Adventures” (a.k.a. Season 4 of Batman: The Animated series). Published in Issue #11, 1999. Written by Ty Temptleton. This story, despite coming from a spin-off series, may very well be one of the most famous Riddler stories out there...and for good reason. In it, the Riddler escapes from Arkham Asylum (again), and goes into hiding. Of course, all of Gotham holds its breath in the aftermath, waiting for the Riddler’s next crime spree...but then there’s a surprise. Instead of leaving clues to his OWN crimes, the Riddler instead chooses to leave clues to the crimes of other people. In this way, he figures, he’ll be able to continue his feud with Batman and the GCPD, but not risk capture, since he never plans to give them a hint as to where he’s hiding, or commit any great crimes himself. There are so many things that make this story great, it’s hard to count. The story itself is pretty clever - having the Riddler leave clues for OTHER villains is just a fantastic concept. I’m a little surprised it had never been tried before! Similarly, in order to get the information on where these crimes will happen, the Riddler essentially turns into a sort of vigilante...but unlike Batman, his code is a lot more…“rough around the edges.” In one scene, he threatens a thug with electrocution if he doesn’t tell him where his old gang’s next caper will be pulled. Nygma seems to take great delight in shocking the man and forcing him to talk, and gleefully exclaims, “Being a good guy is fun!” Nygma himself is brilliantly written here, and brilliantly drawn; he’s got the excitability of a ten year old, but it’s all sort of glossed over by this chilling, intellectual facade. You get through the cracks in the armor, so to speak. Rick Burchett is the penciller here; I’ve always loved his work. He has a great sense of cartoonish, energized style, but at the same time, he’s able to make the characters both sympathetic and intimidating. Something about Riddler’s facial expressions, in particular, really sells him as a creepy character; the TNBA style, mixed with Burchett’s natural talent, gives him an eerie, Hannibal-Lecter-esque vibe in many places...which only makes the moments he goes absolutely berserk, throwing a hissy fit, all the more fun. But the best part of this story is the ending. I don’t want to give it away, but trust me, it’s a twist you will never forget. Give this one a read if you haven’t already.

A Question of Identity.
This was part of the spin-off series “The Batman Strikes!” based on the show “The Batman.” This story was published in Issue #17, 2006, and written by Bill Matheny. In it, the Riddler manages to get hold of some top secret tech from the Federal Government of America itself. That’s already pretty cool. Now, with all this tech, what does Nygma plan to do? He hooks up the stuff to just about every electronic billboard in Gotham City, and using a puzzle-like formula, begins to literally piece together the face beneath Batman’s mask. With help from Alfred (of course) and Detective Ellen Yin, it’s a race against time to find the Riddler before he reveals Batman’s identity to the entire city. It’s a pretty simple but surprisingly intense story; Matheny brilliantly captures the Riddler here...more specifically, he captures the version from “The Batman.” Sometimes in these spin-off comics, writers tend to lose track of the character’s “style,” so to speak, unless they’ve worked in that same universe before. Matheny, however, perfectly captures the Riddler’s speech patterns, vocabulary choices, and basic voice...and, of course, the artistry (pencils courtesy of Christopher Jones) help make sure it stays very clearly in the style of the show. Much like with “Crossed Eyes, Dotty Teas,” from Knightfall, it’s a simple story, but it just SOUNDS good. I don’t really know how to describe it. Still, if you’re a fan of the Riddler (especially the version from “The Batman”), it’s worth giving it at least a quick read.

Other Honorable Mentions (with brief descriptions) Include…
The Riddler’s Prison-Puzzle Problem.
Published in Detective Comics #377, 1968. Written by Gardner Fox (the same writer behind “Remarkable Ruse”). A fun Silver Age story; not much to say about it, to be honest. I just really like this one for some reason. (shrugs)

City Walls.
Not a Batman story, but rather a GREEN ARROW story. Published in Green Arrow #34 - 39, 2004. Written by Judd Winick. Riddler is written really well in this story arc, and plays a pretty major role; it’s also sort of interesting seeing him go up against a different hero, especially since Green Arrow actually has several similarities with Batman, as a character...at least in my opinion.

The House the Cards Built.
Part of the Joker’s Asylum miniseries, published in 2010. Written by Peter Calloway. I have mixed feelings about the story as a whole, but the Joker’s narration, the Riddler’s true motivations, and the twist at the end all lead to a story that’s got plenty of good points in my book.

Description

Riddle Me This: what’s black and green and purple all over? Answer: very obviously, the Riddler! (Not really a riddle, just simply a description...so sue me.)
After making my list of the Top 10 Mad Hatter Comics, I decided that I enjoyed doing that list so much, why not make a couple more lists devoted to my favorite comic stories involving my favorite Bat-Rogues? So that’s exactly what I’m going to do. The Riddler seemed a good place to start because...well, he’s an interesting case. The character is very well-known, and undeniably one of Batman’s most infamous Rogues...but a lot of people seem split on him. ESPECIALLY in terms of his appearances in the comics. Much like with the Mad Hatter, so much of the good stuff we get out of the Riddler comes not from the comics themselves, but from other media, such as television and video games. However, there are some truly great Riddler stories out there, and they deserve to be recognized. So, let’s waste no more time! Slap on a domino mask and prepare to quiz, quip, and query anything you like: these are My Top 10 Favorite Riddler Stories!

10. Crime’s Puzzle Contest.
Published in Detective Comics #142, 1948. Written by Bill Finger. This was actually the Riddler’s second appearance, after he seemingly drowned in his first. (More on that story later.) Popping up alive and well, the Riddler stumbles upon a “National Puzzle Club,” where an awards ceremony is being given. Being the Riddler, he steals the most coveted award, and flees. However, the idea of a puzzle club and/or contest has given Edward Nygma a fantastic idea: what if he stages a Gotham-wide puzzle contest, leaving riddles and puzzling clues where the entire populace can see? The catch, of course, is the prize: every clue leads to his next caper. It’s basically the Riddler doing what he always does, but on a much grander scale than in some other stories. The idea of Edward Nygma deciding to put on a big contest is also pretty fascinating; on the one hand, it fits in with his ego - he lights up billboards, hacks electronic signs, etc. Everyone’s eyes are on him, and everyone’s left wondering. A need for attention and respect is a big part of Riddler’s character, and always has been, so a story like this works well. But the best part is that it works to his advantage both ways: for example, when Batman & Robin inevitably solve one of his clues, Riddler is able to escape into the massive build-up of cars that have come about due to everyone rushing to try and solve his puzzle. He’s not intentionally using the clues as a distraction, so much as he is taking advantage of the times they do. It’s a clever ploy for the character, all around, and leaves us with a very good, and rather underrated, little comeback story.

9. Remarkable Ruse of the Riddler.
Published in Batman #171, 1965. Written by Gardner Fox. What’s MOST fascinating about this story actually is not the story itself: it’s what later became of it. Because less than a year after this story was published, the famous 1960s Batman series - with Adam West as Batman, and Frank Gorshin as Riddler - first aired. And what story did the creators choose to adapt for their first episode? This very one! Now, admittedly, there are MANY differences between the television episode and this comic (as was the case with a lot of the stories directly based or inspired by comics for the show), so that hardly makes the story itself great on its own...but the story IS very good. After a long hiatus (almost twenty years in the real world, in fact), the Riddler comes back to Gotham City, claiming he is ready to turn over a new leaf. (Spoiler alert: he really isn’t.) For his first act - and in a sequence that wasn’t in the T.V. episode - he actually HELPS Batman & Robin capture a bunch of thieving crooks! From this point on, the Dynamic Duo don’t know what to believe - as time goes on, the Riddler seems to be doing some sort of dastardly deed or another, but each time Batman & Robin get close to catching him, they find themselves foiled as its revealed that the Riddler was doing nothing wrong at all. It doesn’t help that Nygma has apparently inherited a large amount of money from his uncle, which often becomes a major issue. In one famous scene, they believe they catch Riddler stealing a jeweled cross from a man at gunpoint...only to find out that the “gun” was actually a novelty cigarette lighter that resembled one, and Riddler had just purchased the cross. He was just giving his “victim” a light! Aside from its connection to the 60s show, it also makes for another great comeback story...again, especially considering, at this time, the character hadn’t been seen in decades. And, once again, it actually does give you a surprising little look into Riddler’s mind: again, he has inherited a large amount of money in this story. But what does he use it for? Taunting Batman & Robin! It really goes to show you that Nygma doesn’t really care about money. Oh, he’s glad to have it, and he finds all sorts of ways to use it, but the ultimate goal is just using it as a little extra something to dangle over the Caped Crusader’s head. The comic also features one of the most famous Riddler covers of all time (pictured above); this is from another scene that didn’t make it into the show, and exactly what’s happening there isn’t revealed until near the end of the story...but it’s a fine bit of silliness when this strange image we’ve been wondering about finally comes into play. It keeps you going, making you wonder just what’s going on and why, which is what a good, eye-catching image should do. For all these reasons, this story definitely deserves some recognition.

8. Solitaire.
And now, for something much more recent. This was part of the New 52 continuity, published in Batman 23.2, 2013. Written by Ray Fawkes & Scott Snyder. Now, let’s talk about the New 52 for just a second: this was an attempt by DC to try and “reboot” many of their famous characters and universes for a new generation. It was...controversial, to say the least. Many fans felt angered by the changes, especially since not EVERYTHING got totally changed, making the timelines more confusing rather than less. And what things were changed, not everyone felt were changed for the better. And, yeah, the New 52 struck out several times - such as the stupidity of “Death of the Family” (sorry if you like that story arc, but I do not...AT ALL), or the mediocrity of “Mad” (the Hatter’s big story arc) - but when it got something right? By God, did it get something right! And the Riddler was a prime example of that. In this story, the Riddler breaks into Wayne Enterprises HQ to get revenge on a guard who abused him back at Arkham Asylum. You see, in Arkham, there was/is a strict “no games or puzzles” rule for Nygma, apparently, and this guard used that to his advantage, not even allowing the Count of Conundrums to play a peaceful game of solitaire. There’s a twist to Nygma’s plot, however, which connects to an overaching storyline...but I mustn’t say more there, or I’ll spoil the surprise. There are so many reasons this story is great. First of all, it really does let us see the Riddler for what many people sometimes forget he is: a genius and a threat. Nygma isn’t just leaving crazy clues all over the place, he’s breaking into one of Gotham’s most secure buildings, and taking out anyone who tries to disrupt his scheme in even the slightest way, and he’s doing it EASILY. The panic of so many of the other characters in the story - such as the former Arkham guard who now works as a security man for Wayne, and the various employees and other security personnel who are there - are contrasted by Nygma. Through the majority of the story, he is calm, poised, and surprisingly quiet. There is, however, one point where the calm is broken: an indignant woman, trying to make a stand, punches the Riddler in the face. His reaction? He starts beating her with his cane, and then shocking her with powerful electrical charges, raving all the while, saying things like, “YOU DO NOT TOUCH ME!” and “You have to know what you are.” It’s clear to us that the Riddler needs one thing perhaps even more than attention: he needs respect, and more importantly (at least in this story), he needs a sense of control. He cannot accept that anything or anyone can “touch him,” figuratively or literally, so when the control is apparently broken, he lashes out. And if anything or anyone besides his intended target is in the way? Either they stand aside, or they get trampled underfoot. Nygma almost feels like a force of nature in this story...which makes the calm and slick twist at the end of the tale all the more interesting. For giving us Riddler at both his most dominant, and his most vulnerable, all at the same time, this story definitely gets a place on the list.

7. The Riddler.
Published in Detective Comics #140, 1948. Written once again by the great Bill Finger. This (as the title may imply) was the character’s first appearance. The thing about the first appearances of many Batman Rogues in the comics is that they tend to be hit or miss - for example, Joker and Penguin came out practically as fully formed characters, but some other villains (such as Scarecrow and Poison Ivy) took time to develop into the characters we know today. The Riddler, thankfully, came out as one of the former. The story gave us the first take on his origin story (which has not so much “changed” so much as simply been expanded upon over time), and provided some of the most famous traps and clues the character would ever use. This was also another story to inspire an episode of the 60s show; this time, it was John Astin’s two-parter as the Riddler, although, once again, there would be a lot of changes from the source material. There’s not much to say about the plot, mind you - basically, Edward Nygma, a man obsessed with puzzles, word games, and riddles, decides he needs greater intellectual challenges in life. So, he decides to commit puzzle-themed crimes, and leave clues to the police (and more importantly, the famous Batman) to try and solve, just to prove how clever he truly is. The traps themselves are delightfully elaborate, the riddles fun, and for a story from the late Golden Age/early Silver Age, it can actually get pretty brutal: for example, the Riddler cages a man in an elaborate trap that will slowly suffocate him as time goes on, and might even crush him to death. The Dynamic Duo have to figure out how to unlock the puzzle cage before the man is utterly destroyed. But, in keeping with the Riddler, neither money nor random death is really what he’s after: he simply wants to create the perfect puzzle, find the perfect mental match, and he sees Batman as his way to accomplishing these goals. It’s a simple introduction, but also a beautiful one.

6. A New Dawn.
Published in Batman Confidential #26 - 28, 2009. Written by Nunzio DeFilipis & Christina Weir. This three-part story arc is most well-known for introducing the character of King Tut, one of the most famous original villains from the silly 60s T.V. show, into mainstream comics. Much like the original, Tut is a man who believes he is the reincarnation of the great pharoah Tutankhamun, nicknamed “King Tut” in popular culture. The big difference is that he is a serial killer, who tells ancient riddles from old Egyptian texts to warn his future victims of their fate. Tut himself, however, is not so much the focus as the REAL conflict of the story: in order to stop this new, riddling menace, Batman is forced to team-up with the Riddler. “I think in riddles,” Nygma argues, reasoning that no one is better to face such a foe, and making it clear his reason for wanting to help is simply “professional pride.” No one is going to more or less steal HIS modus operandi and get away with it. (...Which makes you wonder why he never bothered the Cluemaster or the Puzzler, but whatever; maybe they have a truce of some kind…) What’s most interesting about this story is the way Riddler is portrayed; he’s funny and eccentric, and never really outright threatening...but at the same time, neither we nor Batman himself are ever sure how much we can trust him. The story is also a great showcase for Riddler’s own mind; for a character who is supposed to be Batman’s intellectual equal, many stories seem to forget this, and depict him as something of a fool - a madman who THINKS he’s brilliant, and doesn’t realize his own self-destructive issues. In this story, Riddler actually tends to figure things out before Batman does, and is actually able to use the fact he ISN’T trusted to the situation’s advantage. He’s cunning, he’s manipulative, he’s tricky, he’s snarky and strange...but at the end of the day, and here’s the clincher: he actually DOES help, and not only that, he doesn’t turn right around and try to cause trouble himself. It’s a bizarre little story, introducing a bizarre sort of villain, with a bizarre team-up to top it all off, and one of the most complex and clever portrayals of Riddler you’ll ever find. I ask you, ladies and gents, what’s not to love?

5. Dark Knight, Dark City.
This three-part story arc seems forgotten by a lot of people, which is a shame. It was published between Batman #452 - 454, in 1990, and written by Peter Milligan. The tale focuses on the Riddler concocting another crime spree...but something is very...different this time. The Riddler behaves more maniacally, psychotically, and downright sadistically than ever before. As one of his own goons points out, “You’re making the Joker look downright sensible!” He hangs people, sets off bombs, and even endangers innocent babies in a variety of rather disturbing ways, to say nothing of the horribly treacherous way he treats his henchmen. But here’s the thing: everyone in the story, in some way or another, acknowledges this is NOT normal for him. The Riddler, after all, while not a villain who will shy away from endangering people or spilling blood, doesn’t actively SEEK IT OUT. His schemes are focused on proving his wits, gaining respect and adoration...not senseless violence or brutal slaughter. As the story goes on, it becomes clearer and clearer that something isn’t quite right, and that perhaps Edward Nygma isn’t totally in control of what’s happening. This story, in some ways, sort of reminds me of “The Mad Hatter Flips His Lids!,” one of my favorite Mad Hatter stories: it starts off more or less like a Gold or Silver age story, but in this case, it proves that under the right circumstances, a villain from that age can cause a lot of problems. The difference is that, much like with another Mad Hatter story, “The Wonderland Gang,” this reckless cruelty is NOT the way that villain usually behaves. It ends up becoming less of a classic superhero tale, and more like a Gothic horror story; think H.P. Lovecraft meets...well...Batman. And as someone who loves that genre...well, how can I not give this tale a place high up on this list?

4. E. Nigma, Consulting Detective.
Also sometimes titled “E. Nygma, Consulting Detective.” Published in Detective Comics #822, 2006. Written by none other than the amazing Paul Dini. This was actually one of the first stories in a many-issues-long run with stories all written by Dini: one of the chief creators of the DCAU, and widely considered to be one of the best Batman writers of all time. ESPECIALLY when it comes to the villains. In this story, the Riddler is released from Arkham, and declares that he’s giving up crime in favor of being a crimefighter himself. With his usual flair, he announces he plans to become a private detective! And...he actually means it! He really does want to turn over a new leaf and try his hand at stopping crimes rather than committing them. He’s not doing it necessarily out of the goodness of his heart, since his motivations are more or less the same, but he’s still trying his hardest to give up all the old, villainous habits. Nygma’s new career actually lasted for quite some time (not TOO long, though), and this was just the first story where he began his new job. But, for me, it’s also the best one. In some ways, this story is a lot like “New Dawn”: the Riddler and Batman have to team-up to catch a criminal, and hijinks ensue. The difference, however, is that Riddler is totally sincere about his plans to go straight, and as a result, the rivalry between he and Batman feels all the more humorous. Not only is Batman constantly trying to prove the Riddler is up to no good, both of them are constantly trying to one-up the other. Heck, the only reason Batman ends up solving the case before Nygma (and no, I don’t think that’s a spoiler, let’s all be honest) is because he decided to he just couldn’t let Riddler WIN. He HAD to prove the man wasn’t right. In a way, this almost makes Batman seem as bad as Riddler himself can be. You really do see why the two are such strong equals, and that Batman really does have competition in the form of his old enemy. And because Riddler IS sincerely trying to go straight, you do feel a bit bad for him when he loses; yeah, he’ll have other cases in the future, and yeah, he was sort of an arrogant git...but he’s trying his hardest, and he has to live with the knowledge that his first real case was solved by somebody else. For someone already obsessed with proving themselves the better brain, that’s a tough blow to take, and it haunts Nygma throughout the rest of his time on the job in future stories. Again, “Detective Riddler” would appear in other stories by Dini to come, but this first try of his will always remain the best in my book.

3. Batman: Zero Year.
Published between Batman #21 - 27/29 - 33, between 2013 and 2014 (part of the New 52 continuity). Written by Scott Snyder & James Tynion IV. As I said before, when the New 52 did something right, they did it VERY right. For many, the massive story arc known as “Zero Year” was almost undeniably the best Riddler story to appear in recent years...indeed, some have gone so far as to say it’s the best ever written, period. And, yes, it definitely is one of the Greatest Riddler Stories Ever Told in my book, too. “Zero Year” was a new retelling of Batman’s origins, and his first foray with supervillains in Gotham. Nothing new there, and the story has its ups and downs (more ups than downs, thankfully). But what people loved the most about it was the Riddler. Not only are his origins pretty good, and not only does he play a HUGE role in the events of the arc (in fact, for the last third at least, he’s the main villain), but this was probably the character's BIGGEST story. Because the Riddler succeeds in doing something few other villains have acheived: he all but CONQUERS GOTHAM CITY. I like to call this story “The Dark Knight of Riddler Stories;” it really is very similar, in a lot of ways. Batman is relatively new to his newfound “job,” and he runs into a villain unlike any he’s ever faced before. Someone who can out-think him, someone who is nigh-untouchable, and someone who has just as much of a sense of theatricality as he does. Anyone who says the Riddler is a “wimpy” or “silly” villain should definitely read this arc; they won’t be thinking that for long.

2. The Riddle-less Robberies of the Riddler.
Published in Batman #179, 1966. (Yep, same year the Adam West show went on the air. Yet they never adapted this story...weird…) Written by Robert Kanigher. This story is unique for many reasons: the biggest one being it’s actually rather ahead of its time. If you look at the Silver Age and its villains, while they certainly had their fair share of fun stories, most of the villains then WERE NOT ACTUALLY outright insane. In fact, most of them were not even that threatening. The Comics Code of the time just didn’t allow for a lot of meat on the bones, so to speak, and kids - the primary demographic - were fine with just a bunch of crazy, nonsensical adventures, and parents were cool with it as long as their kids didn’t try anything too crazy in response. So THIS story HAD to make an impact...because it comes right out and calls the Riddler crazy, and actually, in a surprisingly short amount of time, manages to provide a fascinating little character study. The Riddler decides that he’s tired of his self-destructive riddles getting him caught, so he decides he’s going to commit a series of robberies and leave no clues or intriguing puzzles at all. Sounds fair enough. The only problem is that he can’t seem to do it. He feels he HAS to leave a riddle, make up a trap, do SOMETHING other than just take the stuff and go. Realizing he has a problem, he takes some self-help courses to help control his urges...but when he finally does get back into the crime game, he’s left with the ultimate riddle: can he truly commit a crime without any gimmicks? Having a villain cope with their own mental issues, and still making it a fun story kids could understand, and actually making it a real mystery to top it off (read the story to see what I mean there), were actually really groundbreaking ideas for a Silver Age story. It doesn’t help that this was, believe it or not, only the FOURTH TIME Riddler had even appeared in the comics. He wasn’t the infamous Rogue we all know him for today; he was just a minor maniac in a great tapestry of villainy. I am convinced that this story and Gorshin’s work on the television show that came out at the same time are jointly responsible for why the character became so much more popular in later years; we never really got to see a good view of how JOKER’S mind worked, or Penguin’s, or Catwoman’s. Even today, the idea of the Riddler having to try and keep his compulsions under control is still fascinating, making this old time classic just as good a read nowadays as it ever was.

But as fascinating as “The Riddle-less Robberies of the Riddler” is, there’s one story that’s even better...

1. Questions Multiply the Mystery.
Published in Detective Comics Annual #8, in 1995. Written by Chuck Dixon. In this story, Riddler gives us a self-narrated new take on his origins, going from childhood traumas to modern complications. This is a very simple set-up, but the story, itself, is anything but simple. There has never been a more in-depth look at who the Riddler is and why he does what he does than this comic. Everything from his feelings about Batman, to his reasons for loving puzzles, to his relationship with Echo & Query (his most well-known henchgirls from the comics...actually, perhaps ironically, this is the only story in the top ten where they appear), and so much more is covered here. The origin story itself is really good, too. Nygma’s fears of being forgotten, unnoticed, unloved, etc. are all laid bare. But the ultimate twist is this: he HATES telling us all of it. A riddle is only interesting when you don’t know the answer. So what does that make the Riddler when everyone knows his deepest and darkest secrets? As much as he loves to play to the crowd and flaunt his abilities, there are some things he cannot stand to share...but for reasons we’re not wholly sure of until the very end, he can’t stop himself from telling us every last detail. And the twist about what’s really going on that comes in at the end is simply breathtaking. What more do I need to say? For reasons as obvious as why the chicken crossed the road, “Questions Multiply the Mystery” is undeniably the Greatest Riddler Story of All Time.

Honorable Mentions Include...
The Oldest One in the Book.
Part of “Batman: Gotham Adventures,” a spin-off series based on “The New Batman Adventures” (a.k.a. Season 4 of Batman: The Animated series). Published in Issue #11, 1999. Written by Ty Temptleton. This story, despite coming from a spin-off series, may very well be one of the most famous Riddler stories out there...and for good reason. In it, the Riddler escapes from Arkham Asylum (again), and goes into hiding. Of course, all of Gotham holds its breath in the aftermath, waiting for the Riddler’s next crime spree...but then there’s a surprise. Instead of leaving clues to his OWN crimes, the Riddler instead chooses to leave clues to the crimes of other people. In this way, he figures, he’ll be able to continue his feud with Batman and the GCPD, but not risk capture, since he never plans to give them a hint as to where he’s hiding, or commit any great crimes himself. There are so many things that make this story great, it’s hard to count. The story itself is pretty clever - having the Riddler leave clues for OTHER villains is just a fantastic concept. I’m a little surprised it had never been tried before! Similarly, in order to get the information on where these crimes will happen, the Riddler essentially turns into a sort of vigilante...but unlike Batman, his code is a lot more…“rough around the edges.” In one scene, he threatens a thug with electrocution if he doesn’t tell him where his old gang’s next caper will be pulled. Nygma seems to take great delight in shocking the man and forcing him to talk, and gleefully exclaims, “Being a good guy is fun!” Nygma himself is brilliantly written here, and brilliantly drawn; he’s got the excitability of a ten year old, but it’s all sort of glossed over by this chilling, intellectual facade. You get through the cracks in the armor, so to speak. Rick Burchett is the penciller here; I’ve always loved his work. He has a great sense of cartoonish, energized style, but at the same time, he’s able to make the characters both sympathetic and intimidating. Something about Riddler’s facial expressions, in particular, really sells him as a creepy character; the TNBA style, mixed with Burchett’s natural talent, gives him an eerie, Hannibal-Lecter-esque vibe in many places...which only makes the moments he goes absolutely berserk, throwing a hissy fit, all the more fun. But the best part of this story is the ending. I don’t want to give it away, but trust me, it’s a twist you will never forget. Give this one a read if you haven’t already.

A Question of Identity.
This was part of the spin-off series “The Batman Strikes!” based on the show “The Batman.” This story was published in Issue #17, 2006, and written by Bill Matheny. In it, the Riddler manages to get hold of some top secret tech from the Federal Government of America itself. That’s already pretty cool. Now, with all this tech, what does Nygma plan to do? He hooks up the stuff to just about every electronic billboard in Gotham City, and using a puzzle-like formula, begins to literally piece together the face beneath Batman’s mask. With help from Alfred (of course) and Detective Ellen Yin, it’s a race against time to find the Riddler before he reveals Batman’s identity to the entire city. It’s a pretty simple but surprisingly intense story; Matheny brilliantly captures the Riddler here...more specifically, he captures the version from “The Batman.” Sometimes in these spin-off comics, writers tend to lose track of the character’s “style,” so to speak, unless they’ve worked in that same universe before. Matheny, however, perfectly captures the Riddler’s speech patterns, vocabulary choices, and basic voice...and, of course, the artistry (pencils courtesy of Christopher Jones) help make sure it stays very clearly in the style of the show. Much like with “Crossed Eyes, Dotty Teas,” from Knightfall, it’s a simple story, but it just SOUNDS good. I don’t really know how to describe it. Still, if you’re a fan of the Riddler (especially the version from “The Batman”), it’s worth giving it at least a quick read.

Other Honorable Mentions (with brief descriptions) Include…
The Riddler’s Prison-Puzzle Problem.
Published in Detective Comics #377, 1968. Written by Gardner Fox (the same writer behind “Remarkable Ruse”). A fun Silver Age story; not much to say about it, to be honest. I just really like this one for some reason. (shrugs)

City Walls.
Not a Batman story, but rather a GREEN ARROW story. Published in Green Arrow #34 - 39, 2004. Written by Judd Winick. Riddler is written really well in this story arc, and plays a pretty major role; it’s also sort of interesting seeing him go up against a different hero, especially since Green Arrow actually has several similarities with Batman, as a character...at least in my opinion.

The House the Cards Built.
Part of the Joker’s Asylum miniseries, published in 2010. Written by Peter Calloway. I have mixed feelings about the story as a whole, but the Joker’s narration, the Riddler’s true motivations, and the twist at the end all lead to a story that’s got plenty of good points in my book.