By Steve Morris

What’s got rhyming couplets, a homonym or two, an allusion to the Ancient Egyptian Gods… and one evidently simple answer, you simpering buffoon?? Why, one of The Riddler’s confounding conundrums, of course! And if you think that’s elementary, maybe you should try writing a character whose entire thing is being able to fatally riddle you. Or anagram you. Or mutually orthogonal Latin square you. Edward Nygma, the Riddler, is many things, but one thing that any writer will tell you is this: he’s flipping difficult to write for. 

So riddle me this: how do you unravel a Riddler?

The character first appeared in comics in 1948 as the merry antagonist of Detective Comics #140, where he laid out a sumptuous banquet of tricks, traps, and teases for Batman and Robin to overcome. Created by writer Bill Finger with artist Dick Sprang, Eddie immediately stood out as one of the most entertaining of Batman’s enemies yet. In his debut, he runs our heroes through a gauntlet of puzzles. He throws crosswords, jigsaws, mazes and rope puzzles at them with liberal abandon — he even sets up one of those little metal puzzles you get in Christmas crackers for Batman to try and pull apart. He has such a wide-ranging arsenal that you have to imagine he’s already worked out a way to weaponize Quordle. 

Equally key to the character is the sheer ego on him. Riddler likes to send Batman advance notice of his crimes, believing that not even the world’s greatest detective will make sense of the clues in time. As a bonus, he also has a tendency to cheat, ensuring that his tricks are actually unsolvable. His death traps might be welded shut, or his riddles might have subjective rather than objective answers. Sometimes he’ll snare Batman in a deliberately inescapable trap and then brag for pages and pages about how stupid Bats is for not finding the way out. Should’ve brought a welding torch, Batman! Only a fool would forget to carry a canister of Oxygen-Acetylene Gas when investigating the old abandoned pier! 

The pair’s dynamic is terrific fun — it’s a battle of wills between two very clever people, one of whom has rigged the deal. But for the writers tasked with bringing him to life, the Riddler’s reputation is like double-algebra homework. The Riddler may be unique amongst comic book villains for how much more challenging he is for the creative team… than he is for Batman himself. 

Picture it: Not only do you, the writer, have to create a satisfying mystery for Batman and your readers, but you also have to create a puzzle. That puzzle needs to be too smart for readers, too smart for Batman, but must ultimately have an answer satisfying enough to narratively and thematically wrap up your story. Oh, and you have to do this on a monthly schedule, of course. Agatha Christie could never. 

The people in charge of writing the Riddler often haven’t either. The Riddler’s comics history is marked by long dry spells in which creative teams refused to engage with him at all. The high bar of difficulty in writing the character has led various writers to try all kinds of other approaches with Eddie: the latest, in Matt Reeves’ The Batman, depicts a version of Riddler who is an incel-adjacent, too-online, would-be mass murderer who specializes in ciphers and shoddy Spanish translations. But how did the Riddler go from a puzzle mastermind to a campy, colorful caricature and come out the other side as, well, Gotham’s version of the Zodiac killer? How has Eddie endured as one of the most iconic in Batman’s rogue’s gallery through so much upheaval?

Well it helps that every one of the Riddler’s appearances outside of comics has been wildly memorable — especially the first. After going missing for 17 years after he first debuted and was apparently killed off, the 1960s brought a new Batman live-action television show, where Riddler was chosen as the first villain to face off against Adam West’s Batman. Portrayed by a giggling Frank Gorshin, this Riddler’s appearance set the standard, with West claiming that Gorshin’s defining turn helped him find the tone for the show. “I loved that kind of on the edge dangerous acting and improvisation,” West said about working with Gorshin.

Gorshin’s full force approach directly informed the Riddler’s comic book career in the process, even as his riddles evolved from jokey but clever teasers: “there are three men in a boat with four cigarettes and no matches – how do they manage to smoke? They throw one in the sea to make themselves a cigarette lighter! ” into just… jokes, which had no impact on his plans: “what are the chillest twelve inches in the world? Cold feet”. It was Gorshin’s suggestion to switch out his character’s leotard-y costume from the comics for a bowler hat and tailored suit combo, a choice which soon reflected on the printed page. He launched the series, and was arguably one of the most popular villains of the lot, holding his own with Joker, Penguin, and that one Vincent Price played. With a passionate performance in front of a delighted prime-time nationwide audience, suddenly Riddler had a new staying power with viewers – and DC were suddenly keen to make use of the character again. From 1965-onwards he was a somewhat-regular feature in Batman’s comic-book world once more. He wasn’t prolific like Penguin, but he wasn’t on the level of Crazy Quilt anymore.

If Gorshin tore into the scenery with relish, then decades later Jim Carrey crunched it up and spat pieces out like Cookie Monster. Joel Schumacher’s Batman Forever gave a freewheeling Carrey carte blanche to bring unsanctioned buffoonery heretofore unseen into the role of the Riddler, where his manic performance embedded the Riddler in a new era’s popular imagination as a wild, spandex-wearing loon, cartoonish above parody. He did have riddles, interestingly enough – but they were secondary to Jim Carrey being, well, Jim Carrey. The film made £336 million at the box office in the process: the Riddler was left as a household name.They even named a rollercoaster after him.

Yet no matter how well-known the character had become in live-action, his appearances elsewhere remained fleeting. In the iconic Batman: The Animated Series, he appeared just five times in total. Writer and producer Paul Dini explained that this was because the character had the “honor” of being the hardest to write for: “For starters, he’s not much of a physical threat and his reliance on riddles, games, and puzzles brings him awfully close to self-parody,“ he wrote in the Batman Animated behind-the-scenes book. Their version of Riddler was eventually reformed, so the production team could write him off their villain roster and spend more time with Roxy Rocket, which is an understandable choice.

The reliance on riddles was a dilemma which comics writers knew well, and in the years following Batman Forever the comics similarly decided to push Riddler from arch-villain to minor inconvenience. Most notably, he showed up in a trio of Batman stories by Jeph Loeb spanning the late 90s and early 2000s: The Long Halloween, Dark Victory, and Hush. Whilst the franchise around him grew darker and more emotionally complex, Riddler stands out here as a relic of his time, parodied by Gorshin and Carrey to such an extent that there could be no “darker and edgier” version of him. He has Gorshin’s looks, Carrey’s personality, and his riddles were more of an affectation than anything else. During his time being written by Loeb he says things like, “Why did this person get shot? Because he did.” 

At the end of Hush, however, we get the big reveal that Riddler is not only behind everything that happened – but, shock, he knows Batman’s name! It’s a sudden twist which seems like it’s going to foundationally change Batman forever… until Loeb has Batman turn around within a page and punch Riddler out.

The Dark Knight doesn’t care, and nothing’s changed. Readers had been offered growth for Riddler which could set him along equal lines to the other big-name villains who form a gauntlet for Batman throughout the story: it seems like a redefining moment for him which will give the character new motivation, purpose, and power. And with one punch, he goes back to being a joke nobody treats seriously. Shortly afterwards Gotham Knights Hush beat up Riddler in revenge; and quickly after that Detective Comics had him humiliated by Poison Ivy. He was a laughing stock within the comics.

It took a while for anyone to find something for Riddler the washed-up baddie – but when they did it was Paul Dini, the same writer who had struggled with the character during Batman: The Animated Series, who gave Riddler a new opportunity. Dini took over Detective Comics in 2006 with issue #821, and in his second issue as writer he brought back Eddie as a rival investigator to Batman. Riddler’d gone legit, with an office and a secretary and everything! Nobody had to write any more of those bloody riddles, because now Eddie was using his superiority complex for good. Yet the core of the character remained his desire to prove that he was the smartest in the room… especially if said room happened to have some kind of “Dark Knight” vigilante standing in it.

That new Riddler lasted a long time! He was around until 2011, turning back to villany just before DC decided to reboot their entire line of comics as part of a relaunch called “The New 52”. Riddler appears in Batman #1 as just another villain in Arkham, but the creative team of Scott Snyder and Greg Capullo seemed to have something more in mind. Later issues gave us a Riddler who sat quietly in Arkham Asylum, planning… something. But what? To get an idea, we had to turn to another form of media, where Riddler had already started being rewritten for a new mass audience. We had to look at what was happening in the video games.

Starting with Arkham Asylum in 2009, Rocksteady Studios’ Batman: Arkham series found that the character’s predilection for puzzles fit naturally into their need for sidequests and collectibles. Rather than watch Batman spend hours solving puzzles, now players could be Batman and solve the puzzles themselves. Across the course of the next few years they gave players a crash-course in Riddler, as the character went from laughing annoyance to dangerous enemy as the games progressed, setting him up as a much more grim and worrying sign of the times than he’d ever been before. The internet age was here, and Riddler was molded into a keyboard warrior who grew more and more proactive as Batman proved impossible to beat.

Wally Wingert’s perfectly proselytizing portrayal of the Riddler in these games proved an absolute delight, harking right back to the character’s first appearance where he constructed death traps and purple wordplay in equal measure. The games supplemented the character’s comic book roots with a more modern sensibility, however; films like Saw and Hostel presented clear new influences for the character. You can imagine him sat in an old chair like Bruce Wayne in Batman: Year One as an ankle chain flew threw his window: “Yes, father, I shall become a sadist”. In Arkham City, Riddler’s victims suddenly started wearing reverse bear-traps , found themselves strapped into torture devices, and were constantly heckled by Eddie over a grainy video screen. If you did something wrong in the game, Riddler would electrocute or blow up his hostages – a stark horror for anyone who still thought the character was meant to be a camp cartoon. Riddler wouldn’t just enjoy being your superior: he would now punish you for being inferior.

And it was this Riddler who influenced the New 52 version of the character, brought to the page by Scott Snyder and Greg Capullo. Their storyline “Zero Year” presented a preening, sneering Riddler with a grand scale and dark streak. New elements of jealousy and impotent anger were injected into the character: seeking to prove himself the smartest person in the world, he wrecks Gotham City and lords over the people from an almost-ivory tower, appearing daily on billboards to challenge citizens to a battle of wits. Riddler was now the little man who wanted to be the big man, and that superiority complex made the character feel more modern: he was the nasty little troll on twitter who mocks you for getting something slightly wrong. He was the embodiment of “Debate me! Debate me!” as he smugly addressed the betrodden people of Gotham from his position of power.

It was an approach which connected, but also meant that Riddler had to once more come equipped with, well, riddles. And writing them clearly wasn’t easy, as Snyder told ComicsAlliance: “I called in a lot of help, to be honest. I called a lot of friends. ‘I need a riddle that relates to the Gordian Knot, or lions and bees,’ and so there were many, many friends that helped with those. I reserved a couple of days just for those riddles, and I left them out ’til the end.” But the challenge of writing riddles now became the point: once he took over Gotham, he didn’t use riddles to give away his plans: he used them to mock the general public for not being able to keep up with him. The purpose of the riddles became aggressive rather than taunting, in a further sign that the comics were starting to find influence from the bestselling video games.

For the most recent major story to feature the character, The War of Jokes and Riddles, Tom King and Mikel Janin decided to blend the newly violent and scary Riddler with Snyder’s increased scale and the classic willingness to cheat. Their Eddie no longer wants to defeat Batman… he wants to kill him. In fact, Riddler’s first act in the story is to stab a police officer twenty-six times. In an interview King said he wanted Riddler to really shine during the story, and he clearly posits Riddler and Joker as equals. Just as Joker becomes more plotting and conniving through his war with Riddler, so Eddie’s capacity for sadism grows and grows throughout the story. He becomes a serial killer, and a horrifying one at that. 

Which all brings us to this new Batman movie. In the film, Paul Dano’s Riddler is inspired largely by real-life serial killers like the Zodiac Killer, who used to leave ciphers for the police to try and solve. It’s a choice which uncomfortably blends the real with the fantastical: but just as with the Arkham games or War of Jokes and Riddles, Riddler suits the approach unnervingly well. There’s also elements of the comic-book reformation of the character in the way he sees himself as exposing the truth about corruption in Gotham, which nobody else is smart enough to see. The movie clevely plays into the ongoing superiority complex the character has consistently had, but through a slightly different angle.

The purpose of his riddles switches from explaining the crimes he’s about to commit into instead providing rationale for his crimes, in a smart modern twist on the classic approach redesigned for the age of the internet warrior. It leaves his riddles as an important character trait in explaining why this Riddler acts the way he does, and why he fixates on Batman. 

It was also a trait which left director Matt Reeves with a whole lot of riddle-writing research to do. As he told Vulture earlier this year : “If you’re going to do a serial killer mystery with ciphers and puzzle pieces that have to fit together, and riddles, that’s a lot of work! I had like 40 riddle books looking for ones that would fit into my narrative.” Yet it seemed to have paid off, given The Batman’s success at the box office, bringing in half a billion dollars worldwide. As we’ve seen consistently, Riddler projects do well on the screen, even if writing him remains a uniquely challenging task.

So to return to our opening questions: how do you solve a problem like the Riddler, you buffering simpletons?? Well, fittingly, it’s by cheating. 

A riddle is meant to only have one solution – but with reviewers highlighting Paul Dano’s Riddler as one of the best parts of The Batman, we now have three separate iconic versions of the character, each of whom feel unique to the moment they were performed. For a villain who is meant to be fixated on knowing the one correct answer to every riddle, he’s uniquely able to be reinterpreted in endless new ways. He’s gone from being a camp and colorful performance artist to one of the most sadistic and sinister villains Batman can ever go up against. There is no one way to write a Riddler. There’s no single solution! 

And writers will always like the challenge that presents. In fact, Paul Dano himself has just taken up that task, having been announced as the writer for a new Riddler: Year One comic with artist Stevan Subic. That story will be part of DC’s Black Label imprint, meaning it’ll be aimed at readers aged 17+. Bill Finger and Dick Sprang would surely never have believed that their creation could have had such a long life, to the extent he’d be in a prestige series for DC seventy-four years after his debut.

Just when readers think they’ve seen everything the Riddler has left to offer us, and the character is finally exhausted… a new lime-green envelope pops through the door of Wayne Manor to challenge us all once again. It seems we’ll never get tired of trying to unravel the Riddler, and writers will never give up on unraveling the character’s fullest potential. It unites readers, writers, and caped crusaders alike: this time, surely, we’ll crack him.


Detective Comics #140
Writer: Bill Finger
Penciller: Dick Sprang
Inker: Charles Paris


Steve Morris runs this site! Having previously written for sites including The Beat, ComicsAlliance, CBR and The MNT, he can be found on Twitter here. He’s a bunny.


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