Top 10 Riddler Stories!

 

Riddle me this, readers: who is one of Batman's most iconic adversaries that always leaves clues and riddles for the Dark Knight to solve? If any of you actually answered the Cluemaster, we are going to have words. No, it's Edward Nygma a.k.a. the Riddler! Created in 1948, the Prince of Puzzles; the King of Conundrums has become a mainstay in the Caped Crusader's rogues gallery and for good reason. A villain who leaves cryptic riddles and clues for the heroes and readers to solve was bound to make an impression and so he did.

However, despite being one of Batman's most popular villains, the Riddler is also one of the toughest to write. An antagonist who's entire schtick is leaving behind cryptic riddles and puzzles has one big challenge: he's only as smart as the people writing him. Coming up with new sets of challenging riddles each time is not an easy task and as such, there are a lot of writers to tend to treat Edward as a joke simply because it's simpler to write someone who thinks they're smart instead of someone who actually is smart. On the flipside, some writers try too hard to make Eddie come off as intelligent that it starts to feel forced. This is unfortunate because when the Riddler is written well, he's easily one of Batman's best villains. And I'm going to show you the ten strongest examples of this fact!

10.) Burning Questions

by Chuck Dixon & Graham Nolan

Infuriated after being kicked out of his own gang, the Riddler sets his sights on a local talk show. With all of the Arkham inmates free and causing mayhem thanks to Bane, both Batman and the police haven't had any time to respond to the riddles that Eddie has sent them. Not one to quit and constantly seeking attention, the Riddler straps a bomb to his chest and soon takes over the talk show.

While a very simple and straightforward tale, Burning Questions provides a perfect representation of Edward Nygma's character. At heart, Eddie is a raging narcissist who will do anything for attention, all so he can flaunt his self-purported genius. His interactions with the TV host here are a lot of fun, particularly with psychiatrist Simpson Flanders (ha). 

While a fun yarn, there's also a good amount of tension, as the readers aren't quite sure how far Riddler will go and if he has an alternate goal. Knightfall excelled at giving the spotlight to Batman's individual rogues and this chapter is no different.

09.) Solitaire 

by Scott Snyder, Ray Fawkes & Jeremy Haun

With Batman currently missing, the Riddler decides now is good a time as any to make his grand return to Wayne Enterprises to settle some unfinished business from years ago. Unfortunately for him, Eddie is going to have to contend with the many security protocols and defenses that Wayne Enterprises has in place. But this is the Riddler we're talking about, and the Riddler always has a plan.

Solitare does a great job showcasing just how clever and crafty the Riddler truly is, as he effortlessly outsmarts or overcomes every obstacle that stands in his way while infiltrating Wayne Enterprises. We really get to see how dangerous the Riddler is when he is clearly prepared and has thought out every possible contingency. 

However, things become really interesting once we discover that the Riddler is here to settle a score with one of the security guards, George Lesley, here. It turns out that this guard used to work security at Arkham Asylum before transferring to Wayne Enterprises; meaning he and Eddie have some... history. Without going in depth, let's just say that their reunion does not go in George's favor and that the Riddler is not someone you want to cross. 

08.) Riddle of the Jinxed Sphinx 

by Doug Moench, Brian Stelfreeze & Bill Sienkiewicz 

 

Tired of constantly being foiled by Batman, the Riddler decides there's only one path to victory: stop leaving the Dark Knight clues and riddles to his crimes. Sure enough, the Riddler beings pulling off multiple successful crimes and heists, with Batman and the police none the wiser. However, Eddie quickly becomes bored with his string of successes because what's the point of pulling off all these capers if no one knows it's him?

There have been multiple "the Riddler stops leaving riddles" stories over the years, but Riddle of the Jinxed Sphinx is my personal favorite of them. This story shows that Eddie could be a highly successful criminal if he simply stopped leaving riddles that ultimately led to his capture. However, the Riddler has never committed crimes for profit, but rather for attention and to prove his mental superiority. Without that attention, Riddler becomes empty and depressed, feeling that there's no purpose to anything he's doing. Eddie truly is his own worst enemy here, as his compulsion naturally gets the better of him.

07.) Riddled

by Chuck Dixon & Graham Nolan

 

For his latest crime caper, the Riddler abducts the criminal who stole his schtick: Arthur Brown a.k.a. the Cluemaster! Strapping a powerful explosive to his body, the Riddler informs Batman that if he doesn't solve all of his riddles in time, the bomb will detonate, killing Cluemaster and everybody around him. The Caped Crusader must now reluctantly work with Brown to bring the Prince of Puzzles down.

Let's be honest: the Cluemaster has always been a second rate Riddler knockoff with the only interesting think about him being that he's Stephanie Brown/Spoiler's father. Riddled finally makes good use of this otherwise pointless character by having the true Kind of Conundrums put him in his place. The interactions between Brown and Nigma are great as the latter never hesitates to remind the former who the true "Cluemaster" really is. 

Beyond these interactions, Riddled perfectly demonstrates how mentally draining and tedious going up against the Riddler is, as he gives out some of his toughest riddles that constantly leave Batman, Robin and Cluemaster guessing. Facing the Riddler truly is a battle of wits, and few stories portray that as effectively as this one. 

06.) E. Nigma, Consulting Detective 

by Paul Dini & Don Kramer

Having sworn off his criminal ways, Edward Nigma has found a new avenue for flaunting his intellect and making some cash without legal repercussions: by becoming a private detective! And after a wealthy Gotham elite with connections to Bruce Wayne is mysteriously murdered, the Riddler is on the case! But unfortunately for him, so is the Batman. The two old foes must now reluctantly put their differences aside and work together if they intend to bring the killer to justice.

The Riddler becoming a private detective was such a great direction for the character and one that I actually miss a little. Despite technically being reformed, Eddie still hasn't really changed because he's not using his deductive skills to help people, but rather to show off his intellect in a way that won't end with Batman punching him in the face. Speaking of which, the interactions between the Dark Knight and the King of Conundrums are a real highlight of the story, as neither can stand the other, but have no choice since neither is about to give up this case.

While this issue is the highlight of Riddler as a private eye, I highly recommend reading the entirety of Paul Dini's run because Riddler is a key player throughout most of it and has numerous standout sequences. 

05.) King Tut's Tomb

by Nunzio DeFilippis, Christina Weir & Jose Luis Garcia-Lopez

A mysterious new villain calling himself King Tut and even dressing up as the historical pharaoh is going around Gotham City attacking specific targets while spouting ancient Egyptian riddles. Outraged over this new upstart stealing his schtick, the Riddler offers to help Batman solve this case and apprehend Tut. While initially refusing, the Caped Crusader eventually agrees to let Nigma help him as King Tut's attacks become more aggressive. 

Yep, it's another Batman and Riddler team up story, though King Tut's Tomb is arguably the best one yet. Once again, Eddie isn't offering to help the Dark Knight out of any sense of morality, but because he can't stand the idea of anybody in Gotham giving out riddles besides himself. The interactions between the two foes are once again the highlight, as Riddler constantly tries to one-up Batman in his detective work, despite the Dark Knight only caring about catching the killer. 

The reader is also never quite sure what Riddler's true end goal is, which makes for some strong tension throughout. And on a sidenote, King Tut was a really interesting villain and it's a shame DC hasn't really done anything with him since, despite the tease at the end here. 

 

04.) The Riddler: Year One

by Paul Dano & Stevan Subic

Edward Nashton rises from the shadows of Gotham, driven by a relentless need to expose the city’s hidden corruption. This six‑issue miniseries serves as a dark prequel to The Batman, tracing how an unknown forensic accountant becomes the feared Riddler. Paul Dano portrays a man with nothing to lose, whose obsession with unraveling the underworld pushes him toward a terrifying edge.

I never thought a move tie-in comic, written by an actor no less, could be this good, but here we are. The Riddler: Year One is a superb examination of Edward Nashton's character from the film, showing how a lifetime of neglect and callousness can turn even the most unassuming people into monsters. Ever since he was a child, Edward had been, at best, ignored by everyone around him and at worst, belittled. Despite being highly intelligent and gifted, no one has ever given Edward the time of day in his life or even cared to notice him. So when Edward discovers that the law firm he works at is involved in some serious criminal activity, he finally sees this as an opportunity to prove his worth and be recognized. However, after a lifetime of experiencing cold apathy, Edward's moral compass has become warped, and he soon finds himself seeking vengeance rather than justice.

If you're a fan of The Batman (2022), Paul Dano's portrayal of the villain or just good comics in general, this is a must-read.

03.) Questions Multiply the Mystery

by Chuck Dixon & Kieron Dwyer

After his latest incarceration in Arkham Asylum, the Riddler finally decides to spill his guts to the doctors there. He opens up about his childhood, the lack of attention he received, his desperation to be seen as somebody, his motivation for becoming the Riddler and of course, his first meeting with Batman.

While The Riddler: Year One is arguably a more in-depth, layered analysis of Riddler's origins, Questions Multiply the Mystery excels in its simplicity. Edward Nygam wasn't horribly abused or experienced some severe childhood trauma; he was simply an unremarkable child who grew into an unremarkable adult and desperately wanted to be seen as special. After becoming the Riddler to gain the attention he craves, Eddie soon realizes that his intellect is no match for the Batman once he comes onto the scene. Therefore, Eddie begins to rely on his one true talent: cheating. This origin shows that, despite being cunning, the only way Riddler can truly win is by rigging everything to his favor. I find this much more interesting than him being the typical genius character that is so common in comics. 

Make no mistake, the Riddler is smart, but he's not the smartest. He knows this deep down but will never admit defeat and will do anything to win. The perfect origin and motivation for the character.

02.) Dark Knight, Dark City

by Peter Milligan & Kieron Dwyer

The Riddler is back and on a new crime-spree, but something is different this time. Eddie has become far darker, sadistic and violent than ever before as he leads Batman on a grim chase filled with murder and barbarism. It soon becomes clear that Riddler is not himself and something far more sinister, even supernatural, is at play.

Prior to this story, the Riddler had actually been written off by DC Comics as a joke; an outdated remnant of the campier Silver Age who simply couldn't measure up to the darker, more serious Bat-rogues of the Modern Age. Dark Knight, Dark City changed all of that as it showed just how dangerous Riddler could be if he was fully unleashed. Eddie commits unspeakable acts of horror throughout this arc, even going as far as nearly suffocating a baby! While this would normally come off as out of character and overly edgy (common for the 1990s), that's actually the point. The story cleverly depicts something being very wrong with the Riddler as it soon becomes clear he isn't doing any of this of his own volition. It's is a horror story at heart and an excellent one at that. 

Dark Knight, Dark City firmly reestablished the Riddler as one of the Dark Knight's top foes and that the days of writing him off as a has-been were long gone.

01.) Batman: Zero Year

by Scott Snyder & Greg Capullo

The power grid of Gotham City is dead. A permanent blackout has been engineered by The Riddler, who now controls the city's infrastructure from the shadows. In this new, lawless state, a young Batman operates without his established arsenal or allies. His mission is a raw, physical struggle to reclaim the streets from descending anarchy. The city's remaining power sources and communication networks are contested territories. Every move is a test against the Riddler's meticulously planned traps, forcing the Caped Crusader to rely on ingenuity over technology.

Zero Year is, without a doubt, the Riddler's grandest scheme, biggest victory and shining moment as a character. He completely outwits Batman and takes Gotham hostage, where it remains for months. Every time it seems that the Dark Knight has finally gained the upper hand and is about to take his city back, Eddie pulls the rug out from under Bruce and reminds him that he's the one in control. 

But perhaps even more interesting is the challenge that Riddler poses to the people of Gotham. If somebody in the city, no matter who, can come up with a riddle that he can't solve, Eddie will free Gotham from his control and give the people their city back. Why would he do this? Simply put, he wants Gotham to get smarter. Riddler feels that people are getting dimmer and more reliant on things like technology and government, so he has taken over the city in an effort to "help" the citizens realize their own worth and intellect. It's a unique and interesting motivation for the character that hasn't been seen before or since this story. Cleverly written, action-paced, introspective and exciting, Zero Year is the ultimate Riddler tale.