Art by Wil (https://www.wilsur.net/)
Detective Comics #140 was published in October 1948. The first story in the issue, as it had been for so many before, was a Batman adventure. Written by Bill Finger, this story introduced a new criminal to Gotham City: Edward Nigma, an egotistical con man obsessed with using puzzles to demonstrate his intellectual superiority over others. Growing so arrogant that he believed himself clever enough to best not only the police but the Caped Crusader himself, Nigma decided to embark on a criminal career where he would send puzzles as clues to law enforcement hinting at his upcoming heists,(but always cheating or rigging them in some way, such as an answer with a double meaning to mislead authorities away from his intended target). Donning a question-mark patterned costume and rechristening himself as The Riddler, Nigma did end up crossing paths with Batman and Robin, leading them on a chase for a while before his eventual defeat.
While he had an interesting gimmick, Riddler apparently wasn’t the most popular character as he only made one more appearance in the ’40s before vanishing from Batman’s rogues gallery. It wasn’t until 1965 when Nigma was reintroduced to perplex the Dynamic Duo with new baffling crime sprees. With the changing comics landscape of the era, and audiences now embracing more outlandish superhero tales, his campy personality was much better received and he appeared more frequently across issues of Batman, Detective Comics, and The Brave and the Bold. Some of his stories even served as inspiration for episodes of the Adam West-led Batman television series, where actor Frank Gorshin’s portrayal helped make the Riddler into a pop culture icon and cemented him as one of Batman’s greatest foes.
In the decades that followed Riddler has featured in just about every media property connected to Batman. A multitude of actors have portrayed him including John Glover, Wally Wingert, and Cory Michael Smith, each putting their own distinctive spin on the character. Not all of his appearances have done the character justice, however. Some writers choose to depict him as a joke reliant on a childish gimmick, while others feel the only way to make him a “serious” threat is to turn him into a brutal killer using elaborate death traps in the vein of the Saw movies. In my opinion, Riddler is at his best when he’s presented as an arrogant genius who sees crime as a game or intellectual simulation, resorting to violence only if necessary, and ever so frequently struggling with his psychosis. He’s my favorite comic book character ever created, and to celebrate the 75th anniversary of his debut, I’ll be highlighting what I consider his greatest appearances in the comics. Some of these stories you might be familiar with, others I hope you’ll be tempted to pick up and learn more about the baffling brilliance of Mister E. Nigma.
#10: The Death of Batman – Edward Nigma has escaped from prison thanks to the aid of an unknown benefactor. Hours later, a prominent mystery author is kidnapped after a banquet honoring his work. These two events are related, but much to Batman’s surprise Riddler isn’t the one responsible for the abduction – he’s been chosen to serve as Batman’s partner in the kidnapper’s twisted game. Forced into an uneasy alliance, the duo travel across the city deciphering the unknown criminal’s clues, surviving lethal traps in each new location as they draw closer and closer to his end. Stories where Batman and Riddler are reluctant partners on a case almost always provide some welcome entertainment thanks to their clash of personalities: Bruce is stoic, focused, and dedicated to delivering as quickly as possible before innocents are hurt, while Edward prefers to indulge in the fun of solving cryptic clues and brag about his genius or grouse when Batman figures one out before him. This particular adventure also stands out by showing that while Riddler has a clear animosity towards the Caped Crusader for constantly foiling his plans, he also has a grudging admiration towards the vigilante as a worthy foe in their battle of wits. Perhaps he even respects Batman’s intellect, though he would never admit it.
#9: Riddler vs. Cluemaster – An egomaniac like Nigma despises criminals who attempt to rip off his style, which is why he’s long held a deep grudge against Arthur Brown, otherwise known as the Cluemaster. In a three-issue run of Detective Comics, Riddler finally decides to rid himself of this puzzling plagiarist, but simply killing Brown wouldn’t be satisfying enough. Instead Cluemaster has a bomb strapped to him and is made the pawn in Nigma’s latest game, where Batman has to solve a series of clues pointing to locations that he must take Brown to within a time limit before the bomb goes off. Racing against the clock and unexpected hindrances, Batman is under intense pressure to not only keep Brown alive but also figure out Riddler’s secondary agenda. An engaging, action-packed story with Riddler as a manipulative chessmaster, demonstrating that he’s just as dangerous working behind the scenes as he is when actively carrying out crimes. While the big reveal of his scheme is a bit lackluster, the rest of the story more than compensates for that weakness.
#8: When Is A Riddle Not A Riddle? – After the events of the No Man’s Land storyline, several criminals abandoned the earthquake-ravaged Gotham to pick up their villainous enterprises elsewhere. Riddler was one of them. Following a rather disastrous encounter with the Flash and Robin, he set his sights on Manchester, Alabama to get revenge on those heroes by targeting their ally, the young speedster Impulse (Bart Allen). Nigma anticipates a humiliating defeat for the adolescent hero, confident that he’ll never be able to solve his riddles and deactivate the bombs he’s planted around the city. There are just a few small problems with his plan – Impulse has no idea who the Riddler is, has too short an attention span for the criminal’s mind games, and can run at super speed, enabling him to find the bombs before the first clue’s been read. While I’m generally not a fan of stories that treat Eddie as a joke, this one works because it’s not being done maliciously. Bart isn’t mocking Riddler out of arrogance, but ignorance and naivete, and the back and forth between the two as Nigma’s frustration mounts gets absolutely hilarious at times. It’s a fun light read for fans of both characters.
#7: Dark Knight, Dark City – One of the few stories that actually gets the idea of a grittier, more brutal Riddler right. Nigma is embarking on a new crime spree, but he’s raised the stakes significantly. He’s kidnapped several newborn babies and placed them in life-threatening situations, forcing the Dark Knight to race against time and survive hellish traps a he tries to save the innocent infants. Riddler is acting much differently than he did in previous crime sprees; he’s much more willing to kill innocents, and even his own henchmen, to make sure everything follows his carefully laid-plans. What makes this work as opposed to lesser stories like War of Jokes and Riddles is that characters will point out how this murderous behavior doesn’t fit Riddler’s style, and the excuses he makes to explain why he’s become so much more bloodthirsty don’t hold water. This all ties in to the secondary mystery, relating to a secret society that existed in Gotham’s early years and the dark rituals they were a part of. It all ties together well for a dark, gothic tale perfectly suited for Gotham City’s grim defender.
#6: Why Is A Raven Like A Writing Desk? – Riddler didn’t appear often in the 90’s Batman animated series since, as the creators admitted, they had trouble coming up with clever riddles and found that his presence could make the stories too complex. Thankfully the tie-in comic series used him more frequently, and would allow the writers to get more creative with plots. Such as the case with an issue of Batman and Robin Adventures where Nigma escapes Arkham after taking Commissioner Gordon hostage and puts out a challenge for Batman to find them by midnight… or else. Unfortunately Batman and Robin are both out of town on a case, so the responsibilities fall to Jim’s daughter Barbara, aka Batgirl. The issue is mostly a showcase for Batgirl to highlight that she’s just as competent a crimefighter as the Dynamic Duo, with the added motive of her father’s life being in peril keeping us more greatly interested (even if that premise did get overused a bit). We don’t see much of Edward in the story but his sparse appearances give us a greater insight into his mental state, such as his delusion that if Batman can’t solve this riddle that will actually prove he isn’t insane, as well as how tricky he is with what words he uses and any possible double meanings to throw his opponents off guard.
#5: Questions Multiply the Mystery – In the years following the first DC continuity reboot with Crisis on Infinite Earths, many characters were given revised origins and backstories to make them more complex. Riddler’s new history is outlined in this issue where he recounts the events of his life to an interviewer at Arkham Asylum. We learn how a young Edward Nigma was emotionally neglected by his parents and ignored by his peers, a lonely outcast desperate for attention. That chance came when he won a contest at school to solve a puzzle in the fastest amount of time (which he did by cheating, sneaking into the classroom the night before to practice). It did get him noticed, but not in the way he wanted as was now a target for bullies. Still, this awakened something in him: a love of puzzles, and a realization that he could only stand out if he broke the rules. This carried over into adulthood when he grew tired of honest work and felt that crime would be a better use of his talents. But he needed a gimmick if he wanted to stand out – something that would make sure he got everyone’s attention. For the most part this is a great retelling of Riddler’s origins: the root of his mental issues, why he chose puzzles as his motif, and why he would risk capture by sending the police clues. But on rereading it can be a little melodramatic at times, which I think weighs it down a bit. Still a good story, even if it hasn’t aged that well.
#4: The House That Cards Built – For a better psychological profile of Nigma and his psychosis we turn to this tale from the Joker’s Asylum anthology series. During a museum heist Riddler finds himself smitten with one of the hostages, a young woman named Jessica Duchamp. This sudden infatuation leads to the job going awry and him needing to book a quick escape when Batman arrives. Though Nigma escapes capture, he’s still ensnared by his encounter with Jessica. He’s obsessed with her, desperate to win her affection. Of course with she turns down each gesture, having no interest in being romantically involved with a criminal. She becomes the one thing Nigma never expected to encounter – a riddle he can’t solve. And he simply can’t have that. He’ll go to any lengths imaginable to have the answer. But will he be satisfied once he knows the solution? It’s a tragic exploration of Riddler’s mania and how it prevents him from living a happy, normal life.
#3: A New Dawn – Another story where Riddler works alongside Batman and deals with a criminal copying his style. Several prominent men connected with the Gotham Museum of Antiquities have been brutally murdered by an assailant dressed as King Tut, the killer leaving a cryptic riddle before each slaying. Suspecting that Nigma has some involvement with the killings, Batman interrogates him at Arkham. He denies any involvement (insisting that if he was responsible, no one would be smart enough to connect it to him), but offended that someone would steal his m.o. he offers Batman a hint as to where the killer will strike next based on the riddle from the last murder, which proves correct. Riddler then escapes confinement to personally confront Tut over his wounded ego, forging a tenuous alliance with the Masked Manhunter to bring the maniac down. Eddie gets a lot of great moments to shine in this arc with plenty of clever comebacks and one-liners, great banter between him, Batman, and Tut, as well as demonstrating how his obsession can actually be used for good in the right circumstances. It also shows that even though Riddler might not be able to hold his own in a fight, his mind truly is his greatest weapon when placed in life or death situations.
#2: Zero Year – When DC decided to reboot its continuity again for their New 52 run, many of its heroes got revamped origin stories, including Batman. This new imagining of Bruce Wayne’s initial foray into crimefighting after his return to Gotham City chose to pit him against Riddler as the first major costumed criminal threat. Nigma is reinterpreted as a shady business advisor/personal strategist for Bruce’s uncle Phillip Kane, who has some very unorthodox suggestions for how to improve Wayne Enterprises’ public image – such as hiring the Red Hood Gang to kill Bruce in order to drum up sympathy for Phillip. After this scheme fails, Eddie severs his ties with Kane and decides to embark on much grander schemes, setting off a complex plot that essentially cripples Gotham, leaving it under his control. Bruce is pushed to his physical and psychological limits as he deals with each phase of Riddler’s plan, leading to an epic final showdown where he and the allies he’s gathered risk everything to free the city. This is what the 2022 Matt Reeves film wishes it could have achieved.
#1: The Oldest One in the Book – it may seem like an odd choice for a cartoon tie-in issue to take the top spot, but it earns that honor by having what I honestly consider the best Riddler depiction I’ve ever seen. Nigma’s broken out of Arkham again and is determined to stay a free man, but he still can’t control his urge to challenge Batman. His solution – send the Caped Crusader clues that will lead him to other criminals. To gather intel on these crooks he becomes a detective in his own way, bribing, intimidating, and even torturing underworld figures to get the information he needs, regularly fending off accusations that he’s crazy. But as Edward revels in the satisfaction that comes from challenging Batman without putting himself at risk, Batman and Robin are analyzing the clues for any hidden messages that may give away more than their benefactor intended. This issue really captures all the best points of Riddler that I mentioned earlier – he’s alerting Batman to other criminal activities even though this puts his freedom at risk because he savors the battle of wits between them, he wants to intellectually challenge himself by playing detective to root out thieves and murderers, and he violently rebukes anyone who dares to call him insane because in his mind they simply can’t see the genius of his game. And when it all comes crashing down around him in the end, it culminates in a dramatic, haunting realization that despite all his protestations, Nigma might actually be insane. This is a must read.