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15 Crazy Riddler Stories You Should Read – averagebeing

The Riddler is one of the most easily identifiable members of Batman’s rogues gallery but do you know his top stories? Ask anyone to name three or four Bat villains and dear old Edward Nygma is bound to come up more often than not.

When it comes to comic characters, The Riddler is one of the most difficult comic book characters to write and this is said by top creators in the industry.

After all troubling, the Cape Crusader is not a small feat and Riddler does this on a regular basis. A large part of who Batman is in terms of detective skills is because of the Riddler.

Here we listed the top 15 Riddler stories in all of DC comics and Matt Reeves’ The Batman may take one of these as source material.

Note: Please keep in mind that this list of Riddler stories is not exhaustive and we’ve put a lot of work for anyone to easily digest it.

Anyway, Without any further delay let’s dive into the most iconic, brainwashing Riddler stories in DC comics.

#15 The Riddler

#15 The Riddler
Source : DC Comics

Appearance: Detective Comics #140

Why You Should Read:

Every bad guy has a start and for Riddler this is the one that moves the needle. This is a must-read if you want to know about Riddler from his first appearance.

Every supervillain has a beginning, and for the Riddler, his can be found in Detective Comics #140.

The first appearance of the Prince of Puzzlers came in a story titled “The Riddler” in this 1948 book written by Bill Finger and drawn by Dick Sprang.

The story featuring the villain in question is best summed up by a quote found in the book:

“I’m clever enough at puzzles to baffle the police. Why don’t I commit puzzling crimes? I’ll make each crime a duel of wits between myself and the law and fix the puzzles so I’ll always win!”

This early incarnation of the Riddler lacks much of the depth his character would eventually develop.

Still, you can’t have a list of the greatest Riddler stories and leave off his very first one!

The first appearance of the Prince of Puzzles happened in Detective Comics #140, which introduced readers to Edward Nigma/The Riddler.

This early version of the character had mastered puzzles.

However, he studied puzzles so he could cheat at them, making this version more of a con man than the brilliant schemer we know today.

This first appearance kicked off a string of successful heists that would ultimately lead to Riddler’s incarceration, and his newfound desire to one-up Batman with riddles and puzzles.

The movie could pull from this initial origin story, and maybe even Riddler’s love of elaborate death traps.

#14 The Long Halloween

#14 The Long Halloween
Source : DC Comics

Appearance: Batman: The Long Halloween #7

Why You Should Read:

This is a story where the entire GCPD, Batman, and every villain in Gotham tries to uncover the mystery of a new foe. What happens when Riddler is brought into the scene? Can he crack the identity of the new villain?

Batman: The Long Halloween is a 13-issue limited series from the mind of Jeph Loeb with illustrations by Tim Sale.

It follows the Dark Knight during his earliest days of crime-fighting when he’s on the hunt for a mysterious villain named Holiday, who murders people only on holidays.

The seventh book in the series focused a great deal of the story’s attention on the Riddler, and while he isn’t the main feature of the series, he’s instrumental in moving the tale forward.

The Long Halloween is an excellent series on its own, and this book features some interesting takes on the Riddler.

While we only have rumors of one villain in the story so far, fans have always wanted to see Jeph Loeb and Tim Sale’s The Long Halloween series adapted for the big screen.

The storyline is set early in the Dark Knight’s career, and while his role in the story isn’t huge, it is a fantastic piece of the puzzle.

As Batman, the GCPD, and the villains of Gotham City try to discover who the mysterious Holiday Killer is, the Riddler is brought on to the case by the Falcone family.

Riddler’s detective side could factor heavily to his introduction to The Batman, considering rumors that the film will be focusing more on Batman’s own powers of deduction.

#13 The House The Cards Built

#13 The House The Cards Built
Source : DC Comics

Appearance: Joker’s Asylum II: The Riddler #1

Why You Should Read:

Every villain from Batman’s rogue gallery is given a new story here. As expected the prince of puzzles is also given a fresh look but the most interesting part of all these happens from the perspective of the Joker.

If you’re interested in how Joker feels about other criminals they make sure to check this out.

Joker’s Asylum was a month-long special that saw the release of weekly books.

Each one took a look at one of the Dark Knight’s greatest foes, and Edward Nygma got his chance in the second week with this one-shot written by Peter Calloway with illustrations by Andres Guinaldo.

The book is narrated by the Clown Prince of Crime himself, and it goes into the insanity that is the Riddler’s point of view of an insane killer clown!

Bonus: This Riddler story reveals never before seen part of Edward Nigma.

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#12 Riddle Me That

#12 Riddle Me That
Source : DC Comics

Appearance: Batman: Legends of the Dark Knight #185-189

Why You Should Read:

Legends of the Dark Knight features young Riddler and how he saved civilians and kept Batman on his toes.

When Shane Mccarthy and Tommy Castillo took on the book there were no expectations for it but things took a turn with the first story.

Legends of the Dark Knight is one of the best Riddler stories ever that fans can get their hands on.

The story highlights how Riddler saved civilians by giving clues to Batman and a reporter.

But what makes this tale interesting is that Riddler has gone through a major redesign as his youth is explored in it.

The five-part series features amazing detail and backstory of Edward Nigma that hasn’t been seen before.

Some of the most popular riddles were born in this tale as the creators didn’t compromise on anything at all.

Batman: Legends of the Dark Knight is a true example of how good the Riddler can be if written by a creative team.

Fans can come across some mind-bending puzzles that even the Cape Crusader couldn’t solve.

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#11 The Riddle Factory

#11 The Riddle Factory
Source : DC Comics

Appearance: Batman: Riddler and the Riddle Factory #1

Why You Should Read:

Want to know how Riddler trapped Bruce Wayne in a dangerous TV show and forced him to solve puzzles then you must read this story.

Written by Matt Wagner and Dave Taylor, Batman: Riddler and The Riddle Factory features Riddler and citizens of Gotham in a secret TV show.

This show saw Nygma gathering contestants and then placing them in dangerous situations. He further made them answer complex riddles to reveal dirty secrets about their favorite celebrities.

As a part of the celebrity status, Bruce Wayne is bound to enter this show and things get interesting after the Cape Crusaders’ original identity gets in.

Bruce Wayne was forced to solve these riddles and put an end to the Riddler but the real motive of Edward Nigma isn’t just to host a TV show.

Can Batman or the show contestant Bruce Wayne find out Riddler’s true plans?

#10 Pieces Of The Puzzle

#10 Pieces Of The Puzzle
Source : DC Comics

Appearance: Gotham City Sirens #9

Why You Should Read:

Over the years, Riddler’s acts put many people’s lives at stake and this is no different to the girl superhero team. Can they put an end to the Riddler?

Riddler’s main focus is on enjoying crimes while dealing with Batman but Gotham’s female superheroes weren’t impressed with their actions.

Gotham City Sirens is a story where Riddler troubled these vigilantes and they need to settle the score once and for all.

They might not be on the same level as the Dark Knight but they’ve had moments that stomp their authority as superheroes.

While Riddle is looking for another matchup between him and Batman, These girls are chasing the prince of puzzles.

Will Riddler focus his attention on the female superhero team or will he pull off another mind-blowing riddle with Batman?

#9 The Riddle-Less Robberies Of The Riddler

#9 The Riddle-Less Robberies Of The Riddler
Source : DC Comics

Appearance: Batman #179

Why You Should Read:

This story reinvents Riddler with a new set of puzzles that even Batman and Robin together struggled to solve.

By this point, Riddler had been around 18 years and he is recognized as one of Batman’s enticing villains but the character development lacked in all previous incarnations.

Even after 18 years, Riddler is a character that needs further development. Making a villain that toys with Batman himself are no joke.

This Riddler story sorts out the previous mistakes and brings a whole new set of puzzles for the Cape Crusader.

When Riddler returns to Gotham City, He wants a new challenge and puts Batman in all sorts of trouble with the new riddles. Can Batman and Robin save Gotham?

#8 Riddle Me This

#8 Riddle Me This
Source : DC Comics

Appearance: Batman #698 & 699

Why You Should Read:

All these Riddler stories see a face-off between Batman and Riddler but this particular tale pits Dick Grayson against the Prince of Puzzles.

In the future where Batman died, Nightwing his first Robin takes in the mantle of Batman and safeguards Gotham City.

When things go accordingly, Crime in Gotham has suddenly spiked and multiple organizations fight over one another to take over the city.

This results in chaos and the people of Gotham are left vulnerable to the attacks.

Black Mask, Falcone family, and several other crime organizations look to control Gotham. With Riddler being the center of it all manipulating everyone, Can Nightwing aka the new Batman save Gotham and its beloved people?

#7 Dark Knight, Dark City

#7 Dark Knight, Dark City
Source : DC Comics

Appearance: DC Comics Presents – Batman: Dark City, Dark Knight #1

Why You Should Read:

Just when Riddler got hold of Batman, He let him live. Amazed by this move, Batman had to find out Riddler’s end game and this story features a much darker Edward Nigma than the previous incarnations.

Written by Peter Milligan, Dark Knight, Dark City is illustrated by Kieron Dwyer and Mike Mignola.

The storyline features an all-new Riddler with a supernatural touch involved.

This is a much experienced and thoughtful Edward Nigma who got hold of an ancient demon named “Barbatos.”

If the Riddler finished a certain ritual then he would get control over the monstrous demon.

For Batman, This is a strange and unusual game played by Riddler. With no clues left behind, Can Batman figure out what’s actually happening?

#6 Riddled

#6 Riddled
Source : DC Comics

Appearance: Detective Comics #705-707

Why You Should Read:

Imagine not one but two Riddlers. Didn’t quite get it? Riddled features Riddler and Cluemaster teaming up to send Batman in a pointless chase.

We all knew that Riddler’s greatest strength is his biggest flaw but he the way he does crimes still mess with people’s minds and leaves them clueless.

This storyline features not one but two of the prominent masterminds joining hands with each other.

In “Riddled”, The Riddler teams up with Cluemaster as they leave complex puzzles after each crime.

Though the Riddler doesn’t really care about his partner, The duo can be troublesome as they operate under the same wing.

Their complex puzzles are sure to make Batman think hard but the interesting part is where these two send the Dark Knight on a wild goose chase which proves to be pointless.

“Riddled” features both parties going all out in a mental perspective and there sure are a lot of mind games in it but the real question is can the Batman once again find his way to victory or will he lose to the criminal masterminds?

Enough with the cat and mouse act for now. Let’s dive into the top 5 Riddler stories on this list.

#5 Batman: Arkham – The Riddler

#5 Batman: Arkham - The Riddler
Source : DC Comics

Appearance: Batman: Arkham – The Riddler

Why You Should Read:

Batman and Riddler have been playing this game for a long time now but what the Riddler does is just mind-blowing as he gets himself caught by the Dark Knight.

In this story, The Riddler actually gets himself caught by Batman by leaving a trail of easy clues.

But why in the world would he do that?

The same question struck Batman as he walks right into the trap laid by the mastermind criminal.

The Riddler isn’t just a typical foe of Batman, He flaunts his intelligence by locking himself in Gotham prison and thus, Taking his game to a next level.

Batman: Arkham – The Riddler features some of the greatest interactions between Batman and Riddler as the Cape Crusader just gets played by the Prince of Puzzles again and again.

#4 Run, Riddler, Run

#4 Run, Riddler, Run
Source : DC Comics

Appearance: Batman: Run, Riddler, Run #1-3

Why You Should Read:

What to see how it feels when both Riddler and Batman work together?

If you do then it is a must-read for all Batman fans.

Written by Gerard Jones and Mark Badger, Run, Riddler, Run story makes Batman and the Riddler work together.

In a series of high celebrity deaths, Riddler frames Batman for murder. This gets the attention of a super high-tech police force called the “Perfect Security.”

There is a group of private people with advanced suits and gadgets whose members can be compared to a national army.

When this private security takes justice into their own hands, Both Batman and Riddler are forced to work together through Riddler’s own traps to put an end to the organization.

This is such a different yet enticing story that places Batman right beside Riddler as he works his way into breaking down the security forces.

With an army of these high-tech-powered agents connected everywhere, Can the new duo bring down the firm and save innocents?

#3 Hush

#3 Hush
Source : DC Comics

Appearance: Batman #608-619

Why You Should Read:

A new villain Hush has cornered Batman with just a few moves but how does anyone do that?

This brings Riddler into the story as he lays down a detailed plan in finding out Batman’s secret identity.

Note: We are talking about the comic version of Batman Hush, not the animated film.

Though the comic version of Batman Hush is fewer Riddler-focused, This story proves to fit better as it showcases Riddler’s brilliance in finding out Batman’s identity.

Batman Hush features Edward Nigma’s master plan as he plays a major role in dismantling the Dark Knight’s life.

With Riddler and Hush working together, Batman has nowhere to go and his secret identity is finally revealed to the bad guys.

Can the Dark Knight take down two of his greatest nemesis and safeguard his identity?

#2 Edward Nigma, Consulting Detective

#2 Edward Nigma, Consulting Detective
Source : DC Comics

Appearance: Detective Comics #822

Why You Should Read:

Ever wondered with all the brilliance, Why did Riddler become a criminal?

This story explains just that.

Even though Riddler is a criminal mastermind, He didn’t plan out to become a supervillain.

In fact, most people do not consider themselves evil until they reach a point in life that turns them into one.

The same goes with Edward Nigma.

Paul Dini took over the complex supervillain and re-introduced him as a private detective who works alongside Gotham Police to solve crimes.

Yes, Riddler indeed turned good. Though it may not last long, This story explains why Nigma became the Riddler and does what he does.

Fans can get right into the heart of Edward Nigma and understand his story completely after reading this storyline.

Not to brag about it but Riddler even works alongside Batman to save people and The Dark Knight trusts him at a certain point.

If you are a true fan of puzzles then this one among all Riddler stories is a must-read from DC comics.

#1 Zero Year

#1 Zero Year
Source : DC Comics

Appearance: Batman #24-25, Action Comics #25, Batgirl #25, Batwing #25, Batwoman #25

Why You Should Read:

This story reimagined Batman’s whole tale in a completely new direction. Though the key focus is on the Cape Crusader, Riddlers gets a ton of moments to shine.

If you want to know more about this enticing new story then this is a must-read.

Redoing Batman and Riddler’s origin takes a huge toll but the New 52 arc does it beautifully.

Written by Scott Snyder and Greg Capullo, This story features Batman in his early days of crime-fighting as he waged a war against all criminals.

Riddler’s origin is drastically changed as he is now a strategist under Philip Kane.

When Nigma suggested killing Batman to solve all their troubles he refused and that lead to the birth of Riddler.

The new Riddler is a force to reckon with as he takes over the entire city of Gotham and makes them play his ridiculous puzzles in order to survive.

Our best guess is that Matt Reeves’ The Batman takes source material from Zero Year as this may just be one of the greatest incarnations of the Prince of Puzzles ever seen on the big screen.

What do you think of the above Riddler stories? Which one will you read next?

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