The best Riddler stories to read before The Batman

Starting the first week of March, audiences everywhere will meet Matt Reeves’ version of one of Batman’s most infamous foes, the Riddler, in the new film The Batman.

Played by Paul Dano with an aesthetic apparently based on the unidentified real world serial killer known as the Zodiac, the new version is a far cry from the madcap antics of Frank Gorshin from Batman ’66, or the cartoon clown played by Jim Carrey in Batman Forever. 

However, the fact that there might be more to the Riddler than a question mark cane and fifth-grade puzzles won’t shock comic book fans. In honor of the villain’s new big-screen form, here are six of the best Riddler comics that show off his many different sides. 

 DETECTIVE COMICS #140  (Dick Sprang, Bill Finger)

Detective Comics #140 cover

(Image credit: DC)

At the risk of being predictable, we’re going to start at the beginning, with the introduction of The Riddler to comic book fans in 1948. This issue of Detective Comics is about as “Silver Age” as you can get from a Golden Age comic book, with the Riddler’s schemes involving a giant steel brain teaser, giant crossword puzzle, and giant corn cob. 

But for all its thoroughly enjoyable goofiness, Detective Comics #140 introduces elements of Riddler’s character that have lasted his decades-long history. Here we learn that Nygma’s turn to villainy stems from a desperate need to prove himself smarter than everyone else, including Batman. 

The issue introduces us to his self-destructive compulsion to allow Batman a way out of every one of his traps. And of course, this comic introduces the Riddler’s incredible intellect which, in contrast to many of his stories that followed, actually proves greater than the Dark Knight’s in the end. You’ll have to read it to find out how. 

 HUSH (Jeph Loeb, Jim Lee)

Batman #619 cover

(Image credit: DC)

It was the comic storyline that made everyone remember how smart Riddler really was. To say much more would be to spoil too much of the plot, so if you haven’t already checked out this incredible comic or the animated adaptation of the same name, make it a priority. It’s not just one of the best Riddler stories, but one of the best Batman tales as well. 

Lee & Loeb‘s vision for the character is perfectly in line with his origin, but it takes his need for proving himself to a different place. What makes Hush a stand out in terms of Riddler’s characterization is his sense of self-awareness. Riddler’s actions in this book are driven by the fact that Gothamites (and maybe even casual comic readers) see him as a c-list villain. 

But rather than make a fool of himself trying to publicly prove them wrong, Riddler uses this information to his advantage, initiating a plan that left still visible scars on the history of Batman and Gotham. 

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Zero Year (Scott Snyder, Greg Capullo)

Batman #32 cover

(Image credit: DC)

Writer Scott Snyder recounts the advice Grant Morrison gave him on writing Batman as “come up with a beginning, come up with an end.” 

We’re of course paraphrasing here, but Snyder listened to Morrison’s advice, teaming up with Greg Capullo to give a ‘beginning’ to the New 52 Batman in the Zero Year story arc. In it, Gotham City is on its knees, and the architect of its collapse is Edward Nygma.

Zero Year is a kind of origin story for both Batman and the Riddler, but it’s also a consummation of everything the Riddler character has ever tried to be. He proves himself the deadliest, and more importantly, the smartest criminal Gotham has seen so far, ascending to its highest position of power in the ruins of civilization he left in his wake. 

Of the many things Riddler has been over the years, ‘urban warlord’ is perhaps one of the most memorable.

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Detective Comics #822 cover

(Image credit: DC)

Speaking of roles that the Riddler’s played, one that is far and above the outlier is when Edward Nygma took on the mantle of hero. 

Yes, you read that correctly. After the events of Infinite Crisis, Edward’s eviler compulsions temporarily leave him, but his brilliant mind stays intact. Still very much into puzzles, Nygma starts his own crime-solving business, beginning to put away the same type of criminal he once was.

E. Nygma, Consulting Detective is the title of Detective Comics #822, but Riddler’s arc as private investigator lasts long beyond that issue. It’s notably successful, too. As a detective, Riddler is trusted by Mary Marvel, Nightwing, and even Batman himself to solve difficult criminal cases. And yet, the worst angels of Nygma’s nature were never too far from his reformed self. 

Even before the New 52 reset the board and cast Riddler back into the villain role, Nygma was having doubts about staying on the right side of the law. Perhaps there’s something just less fun about outsmarting only criminals, we’ll never know.

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Batman #27 cover

(Image credit: DC)

His time as a detective saw Riddler matching wits with a lot of smaller villains, but Tom King and Mikel Janín’s revolutionary Batman run pit him against his toughest criminal opponent to date, the Joker. 

Fortunately for Nygma (and unfortunately for Gotham), Riddler is a villain himself in this iteration, waging a war for the city’s soul in a way that’s just as cutthroat and merciless as the Clown Prince of Crime himself. 

Riddler has often been referred to as a “master strategist,” but that’s never made more clear than in The War of Jokes and Riddles. This is Riddler at his most Napoleonic, not just leading an attack on Joker but also courting the rest of Gotham’s underworld to take up arms alongside him. 

Though the Rebirth Batman run is worth reading in its entirety, this chapter is especially worth your time, if nothing else because the last person to join Riddler’s cause is someone completely unexpected. No spoilers here, but get ready for a shock.

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 DARK KNIGHT, DARK CITY (Peter Milligan, Kieron Dwyer)

Batman #454 cover

(Image credit: DC)

If we’re talking shocks, you won’t find more in a Riddler story than in Dark Knight, Dark City. This gothic tale presents the Riddler as nothing less than a horror movie villain, entirely unhinged and full of bloodlust in his evil. The reason for his vileness dates back to 1765, when an occult-obsessed Thomas Jefferson (yep, that one) attempts to summon an eldritch entity of darkness. 

After discovering records of his activities, Riddler forms his own obsession with the ritual, pledging his brilliant mind and tattered soul to committing its downright despicable steps.

With the release of The Batman fast approaching, there’s a lot of chatter on social media about Matt Reeves giving us “the darkest Riddler yet.” And though it’s entirely possible that will turn out to be true, he’s got a long way to go to match the Riddler of Dark Knight, Dark City. 

Not that he has to be, of course. Darkness, like silliness, practicality, or even villainy, doesn’t have to match across the many iterations of Edward Nygma. Looking down Riddler’s seven decades of history, the only thing that we can be sure of is that he’s always a bit of a mystery. 

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We’ve been singing Riddler’s praises here, but did he make our list of the Best Batman Villains of All Time? That’s a riddle you’ll have to click the link to answer.

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