10 Best Riddler Stories in DC Comics History

The Riddler is not only a major Batman villain, but one of the most interesting characters to come out of Gotham City. With an inferiority complex that makes him hold cities hostage just to play games with the Dark Knight, the mental terrain of DC’s most intelligent villain provides some compelling stories.

Puzzle after puzzle, the Riddler has been putting Batman through the ringer for well over seventy years, but Batman has come out on top nearly every time. The Riddler has had a lot of redesigns throughout the years, too, some odd and some dark, but throughout it all, one thing is clear: the Riddler must be smarter than Batman. In the best Riddler stories out there, the man in green always has a plan, and if those plans can be wrapped up in a nicely rhyming riddle – even better.

10 The Riddler’s First Appearance Will Always Be a Classic

Detective Comics #140 by Bill Finger, Dick Sprang, and Charles Paris

There’s nothing quite like the original. The Riddler’s debut appearance in Detective Comics #140 by DC veterans Bill Finger and Dick Sprang was enough to solidify him a permanent place among Gotham’s rogues. The Prince of Puzzles himself, an epithet long forgotten, goes up against Batman and Robin for the first time, by creating all sorts of traps, wordplays, jigsaws, and mazes.

This version of Edward Nigma – later known as Nygma – is much more a huckster than his later counterpart, who seems to have a full obsession that admits him into Arkham Asylum. Instead of having a near-genius intellect, the Riddler is a trickster, weighing dice and counting cards to win at his own games. Eventually, he fashions himself smart enough to out-puzzle the law and Batman by rigging his own puzzles to his advantage. The Riddler is then born, clad in his famous question marks.

9 The Riddler Rivals Batman’s Detective Skills

Batman: The Long Halloween by Jeph Loeb and Tim Sale

The Riddler’s talents come in handy for something other than criminal enterprise and making Batman chase his own tail in The Long Halloween by Jeph Loeb and Tim Sale. In one of the best Batman stories, the Holiday Killer is still at large, and both Batman and the Riddler are playing detective on April Fool’s Day. Hired by Carmine Falcone to investigate the murders of his criminal family, the Riddler shows his intellectual expertise in solving the riddle of Holiday’s identity.

In the end, the Riddler guesses wrong and loses the Holiday game. Surprisingly, he becomes the next target of the Holiday killer – only he is the one victim who is spared completely, leaving him to wonder about a new riddle: “When does a killer not kill?” As it turns out, Batman is the better detective, and the senseless world just doesn’t conform to the Riddler’s easy questions.

8 The Riddler’s Origin Gets a Mysterious Makeover

Secret Origins Special #1 by Neil Gaiman, Bernie Mireault, Matt Wagner, and Joe Matt

Neil Gaiman, famous novelist and creator of The Sandman universe, enlisted the help of Bernie Mireault for the Riddler’s appearance inSecret Origins Special #1, which tells “new” stories about some well-known Gotham villains. In a future timeline, the Riddler is a cryptic old man with opinions on the young and modern criminals of Gotham. These criminals try to interview him, but he answers every question with a question of his own, cementing a new (but not definitive) origin.

Riddle me this: The greatest of my strengths is that I know my worth. I hug myself so tightly at every birth. What am I? Check out the answer at the end of the page!

This comic is influential to the mythos of the Riddler, who has changed names through the years, alternating between Edward Nigma/Nygma and Edward Nashton. It allows him to become a character much like the Joker, who can’t be trusted to tell the truth. This version of the Riddler is much more a trickster, paying homage to his original self while he also disappears completely into the riddles he creates.

7 Batman Finally Outsmarts the Riddler in a Dark Twist

Batman: Gotham Knights #6 by Walt Simonson, John Paul Leon, and John Workman

In a backup story from Batman: Gotham Knights #6 – and later to be collected as a part of the Batman: Black & White series – “The Riddle” by legends Walt Simonson and John Paul Leon is a deep look into both Batman and the Riddler’s obsession with each other. In this version of their history, Batman isn’t begrudgingly answering the Bat-signal every night, but just as obsessed with being smarter than his opponent as the Riddler is.

Edward Nigma rushes to a house of Alice in Wonderland memorabilia after its collector dies, and his goal is to finally solve Lewis Carroll’s riddle: “why is a raven like a writing desk?” After many fantastical trials, he captures the answers – only to discover that Batman has been waiting there for him and possibly substituted the riddle’s answer for a fake answer of his own, leaving the Riddler to fall into a madness much like another underrated Batman villain, the Mad Hatter.

6 The Riddler Discovers a Riddle He Can’t Solve

Joker’s Asylum II: The Riddler #1 by Peter Calloway, Andres Guinaldo, Raúl Fernández, Tomeu Morey, and Pat Brosseau

In the one-shot Joker’s Asylum II: The Riddler #1, Edward Nigma takes the spotlight as the main character in this fantastic comic that’s narrated by the Joker as he cycles through the Gotham rogues in order to detail how they are just as villainous as him. In this story, the Riddler is approached by a mysterious figure who enlists his help to finally kill Batman – only the figure’s identity is never revealed, becoming an unanswered riddle.

Riddle me this: I can be cracked. I can be made. I can be told. I can be played. What am I? Check out the answer at the end of the page!

That’s not the only riddle in the comic, however, as Edward also falls in love during a heist and then finds himself trying to solve the riddle of love itself. This comic offers an opportunity to not only delve into the mind of the Riddler but to humanize the villain. There’s truly no riddle as unsolvable as love.

5 A New Riddler Debuts and Seizes All of Gotham

Batman: Zero Year by Scott Snyder and Greg Capullo

There are more than enough origin stories and timeline reboots in the DC Universe, but the New 52’s Batman: Zero Year features an origin for more than just Batman. In Batman’s first year as the Dark Knight of Gotham, his detective skills (and his survival skills) are put to the test when the Riddler sends the city into a complete blackout and holds Gotham hostage until Batman solves his riddles.

This storyline steers the Riddler away from being a silly trope into a mastermind of staggering proportions. It also completely solidifies Edward Nygma as Batman’s intellectual rival over every other Gotham villain – even eventually being declared the equal of the Joker. It’s not often that a single Batman rogue can wrest control of Gotham, but Batman always comes out on top and solves the Riddler’s games.

4 The Riddler Becomes Batman’s New Sidekick

Detective Comics #822 by Paul Dini, Don Kramer, Wayne Faucher, John Kalisz, and Jared K. Fletcher

One of the best one-shot Riddler stories of all time, “E. Nigma, Consulting Detective” from Detective Comics #822 features Edward Nigma coming out of a coma forgetting nearly everything about his life of crime. The Riddler is quickly hired as a detective for his deduction skills, and he and Batman embark on a tense buddy-cop quest to solve a mystery together. Instead of their usual hero/villain dynamic, some of the best comedic moments between the two happen right in this issue.

As an ultimate insult to Batman, he and the Riddler actually work quite well together, considering their intellects are alike. The Riddler even nearly comes out on top, solving the case and getting away with a new criminal undertaking – that is, until Batman outsmarts him, like the World’s Greatest Detective he is.

3 The Riddler Gets His Darkest, Most Realistic Treatment

Batman: One Bad Day – The Riddler #1 by Tom King, Mitch Gerads, and Clayton Cowles

The award-winning team of Tom King and Mitch Gerards took a completely different look at Edward Nygma in Batman: One Bad Day – the Riddler #1, a piece of the One Bad Day series in which iconic Gotham villains got their own dedicated story. In this one-shot, the Riddler kills a man in broad daylight, and Batman is tasked with not only solving the crime but figuring out exactly why the Riddler would change his own methods so brutally.

Riddle me this: What is the beginning of eternity, the end of time and space, the beginning of every end, and the end of every race? Check out the answer at the end of the page!

Celebrated as the most original Riddler story ever, this comic takes both the Riddler and Batman into a bleak extreme that doesn’t feel like Gotham at all but much more like the senseless violence of the real world. Suddenly, the riddles turn from silly turns-of-phrases into random acts of absurd violence. In the end, this riddle is unanswerable, and the Riddler will continue to be reborn until fans finally have an answer to the question of who he really is.

2 The Riddler Gets Serious in His Rebirth-Era Takeover of Gotham

Batman: The War of Jokes and Riddles by Tom King and Mikel Janín

Another reinvention of the Riddler, King and Mikel Janín’s Batman: The War of Jokes and Riddles reveals exactly when Batman was finally tempted to kill one of his rogues – and it wasn’t the Joker. The Riddler emerges as Gotham’s ultimate villain with a new question mark scar on his chest as his emblem. For the first time, Edward Nygma wasn’t just a sniveling intellectual but an imposing physical force like every other Batman villain.

At the conclusion of the war, it’s finally revealed that all the Riddler wanted to do was cure the Joker’s depression. For all the deaths he had caused in the city, Batman decides to kill the Riddler, and when the Joker himself stops Batman from crossing his own line, he finally starts to laugh. After this story, all three characters are never the same, and Batman doesn’t emerge exactly victorious.

1 The Riddler Is at His Peak in This Plot Against Batman

Batman: Hush by Jeph Loeb and Jim Lee

The best Riddler story of all time isn’t even a Riddler story until a reveal at the very end of the comic. Batman: Hush by Loeb and Jim Lee is a mystery that tears apart the Bat-Family and introduces Hush to Gotham. In it, Edward Nigma is offhandedly captured trying to rob a bank, which serves initially as a red herring. But then the truth comes out: he’s been the mastermind all along.

The Riddler’s knowledge about the identities of the Bat-Family is what cements his plot. He gathers all the Gotham rogues and plans to tear down the Dark Knight’s psyche with his greatest fear: losing Jason Todd. While Nigma doesn’t exactly outsmart Batman, he certainly does some lasting damage. This story shows just how brilliant the Riddler is and how far he has come from simple riddles to overarching plots that make up one of the best Batman comics of all time, starring one of the best villains of all time: the Riddler.

Riddle 3 Answer: the letter “e”