10 Riddler Comics Which Batman Fans Can’t Afford to Miss

Batman has such an iconic rogues gallery, and Edward Nygma, AKA the Riddler, is one of the very best among that lauded group. From goofy prankster to terrifying killer and everything in between, Batman comic writers are constantly finding new and exciting ways to reinvigorate the Riddler’s image, making him an unpredictable force of nature.

The Riddler’s mental prowess and carefully concocted schemes have kept Batman on his toes for almost eighty years. With appearances spanning timeless classics like The Long Halloween and modern character studies such as Riddler: Year One, there’s no doubt that the Prince of Puzzles belongs in the upper echelon of Batman’s rogues.

10 Bill Finger and Dick Sprang Brought Riddler to Life in Gloriously Campy Fashion

Detective Comics #140

The Riddler’s very first appearance also happens to be one of his most fun stories. In this 40’s era tale written by Batman co-creator Bill Finger and penciled by iconic Batman artist Dick Sprang, Batman and Robin must thwart the Riddler’s attempts to rob Gotham citizens. The Dynamic Duo must solve a series of convoluted (and often hilariously impractical) riddles, including giant-sized jigsaw puzzles, trucks carrying enormous cobs of corn and impossible-to-escape glass mazes.

Though Edward Nygma would only appear once more in Detective Comics before being set aside for the better part of seventeen years, this early crime caper is a wonderful example of the kinds of silly and imaginative characters coming from this era of Batman stories. This was the launching pad for one of Batman’s most important supervillains, and it still holds up today as an engaging and silly superhero romp.

9 Jeph Leob and Tim Sale Let The Riddler Shine as a Supporting Player

Batman: The Long Halloween

One of Batman’s most iconic stories, The Long Halloween,doesn’t feature Edward Nygma’s Riddler all that much, but his presence serves as an exciting wrinkle in an already complex web of mystery and crime. As murders take place on major holidays throughout the year, Batman works together with attorney Harvey Dent and GCPD commissioner James Gordon to try and find the culprit, while less savory characters turn to other means.

The Riddler is hired by Carmine Falcone to find out the identity of the “Holiday Killer,” a task which he is unable to achieve. The Riddler’s role here mirrors Batman’s own investigation in an interesting way, there are certain moments where it almost becomes unclear whether the book’s narration is coming from the Dark Knight himself, or from the devilish Riddler and his own investigation. These blurred lines between good and evil is a major theme in The Long Halloween, and it is one of the reasons why this serves as an excellent Riddler story, as well as a classic Batman tale.

8 Matt Wagner and Dave Taylor Delivered A Mixture of Whimsy and Terror

Batman: Riddler and the Riddle Factory

Moving away from the light-hearted tone of early Riddler stories, this standalone graphic novel finds Edward Nygma putting together his very own reality TV show, a quiz-show called “Riddle Me This,” which he runs from an assortment of abandoned buildings across Gotham City week after week. The show is more than it appears, however, as Riddler uses it as a grisly means of killing powerful Gotham citizens and as a distraction while he pulls off a major heist.

Written by Matt Wagner with art by Dave Taylor, the book is full of plenty of Nygma’s iconic brain-teasers, and while his overall demeanor remains closer to the early days of the character than, for example, Paul Dano’s portrayal in The Batman, but the seeds are there for what the villain will become — a more serious, more obsessive character whose brain-teasers and puzzles now routinely put lives at stake.

7 Scott Snyder and Greg Capullo Brought Riddler’s Villainy Into The Modern Age

Batman: Zero Year

Scott Snyder’s run on Batman is one of the most celebrated superhero series of the last twenty years. His takes on the established Batman mythos and fresh new ideas like Talon and the Court of Owls were huge hits with fans, so it was only a matter of time before he put his own spin on a Batman origin story, and of course, on the Riddler himself.

This time around, Batman finds himself up against a terrifying version of the Riddler who takes Gotham hostage, while having to contend with foes like Doctor Death and The Red Hood gang. It’s the perfect story for an early-days Batman, as it forces him to use both his brawn and his brains to combat multiple enemies on multiple fronts. The Riddler has never been a physical match for the Dark Knight, but his mental prowess makes him one of Batman’s most formidable foes, and this story captures that perfectly.

6 Tom King and Mikel Janin Reinvented The Riddler’s Relationship to Other Batman Villains

Batman: The War of Jokes and Riddles

Though writer Tom King’s run on Batman was often a source of debate among readers, his and artist Mikel Janin’s storyline “The War of Jokes and Riddles” was generally well-received, even by King’s more outspoken critics. The story follows a younger Batman as he navigates a growing tension between The Riddler and The Joker, with the safety of Gotham City hanging in the balance.

This modernized iteration of Edward Nygma is more in line with readers’ idea of what supervillainy is, and though he is still obsessed with riddles, this version of the character is more serious, more conniving, and all the more dangerous for it. Sprawling across eight issues, this storyline is an excellent look at Batman and Riddler’s relationship, especially in comparison to the Dark Knight’s relationship to The Joker. It’s an epic, big-scale story about the dangers of a man whose brilliant intellect is used for sinister means, and the lengths Batman will go to stop him. King’s writing for both Batman and Nygma in this story is refreshing, engaging and often terrifying.

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Batman: Hush

Perhaps the most iconic Batman story of the 21st century, Batman: Hush by Jeph Loeb and Jim Lee follows the World’s Greatest Detective as he tries to uncover the identity of a dangerous new criminal in Gotham City. This hunt leads him into contact and conflict with numerous members of his famous rogues’ gallery — culminating in a tense verbal showdown between Batman and the Riddler.

One of the best interactions in all the two characters’ collective history comes from Hush, when Riddler reveals that he has deduced Batman’s secret identity. Knowing how his obsessive enemy thinks, Batman challenges him with the plain and simple fact that if Riddler were to reveal his secret to the world, it would become worthless. It’s an exceptional piece of character writing for Nygma, placing his obsession in direct contact with his own self-interest, and it stands as one of the most iconic interpretations and examples of Batman and Riddler’s constant mental duels.

4 Tom King and David Marquez Put Riddler At The Center of A Twist-filled Heist

Batman: Killing Time

Another story which doesn’t solely focus on The Riddler, but is benefited by his presence nonetheless, Tom King and David Marquez’s Batman: Killing Time is a crime caper filled with exciting heists, ancient secrets, and constant double-crosses. When the Riddler and Catwoman learn of a dark secret Batman has been holding onto, they plot to steal it from him and sell it to the highest bidder. Along the way, they come into contact with The Penguin, Clock King, Killer Croc, and a mysterious new character called The Help.

Killing Time is a wonderful piece of mystery and action, and the Riddler’s position in the story is especially engaging, plagued by his compulsion to leave clues behind for Batman to follow. The ways in which this puts him at odds with his companions is wonderful to see play out, and David Marquez’s art suits the book’s tone perfectly. It’s a fast-paced, globe-trotting adventure that perfectly encapsulates the Riddler’s fixation on leaving clues behind at the scene of a crime.

3 Paul Dano and Stevan Subic Made The Riddler Frighteningly Relatable

Riddler: Year One

Set in the world of Matt Reeves’ The Batman, this book explores the story of Edward Nashton, who will soon become the infamous Riddler. Written by actor Paul Dano, this DC Black Label book is harsh, emotional and character-driven. Batman is far less central in this story than the titular villain himself, something that is often not the case with Riddler stories.

Placing the series in the world of The Batman, Riddler: Year One allows the audience to gain a deeper understanding of the character they’ve seen terrorizing Gotham on the big screen, as well as empathize with his thoughts, feelings, and actions. Not only does this serve as an excellent companion-piece to the film, but it also serves to highlight the depth and possibility of a character like Riddler in any medium.

Batman: Dark Knight, Dark City

Writer Peter Milligan and artist Kieron Dwyer take on the Dark Knight and his expanded mythos in this game-changing story arc from the pages of Batman. Here, the World’s Greatest Detective finds himself wrapped up in a strange, occult mystery that has ties to the history of Gotham, terrifying bat-demons, and, of course, the Riddler. This is perhaps Riddler at his most terrifying. Forgoing the use of simple puzzles and riddles, Edward Nygma forces Batman into a myriad of emotionally and physically draining trials, all in the service of a deeper, more insidious plot.

As a character often grounded in realism, Riddler’s dive into the mystical and macabre is equal parts shocking and radically compelling. Milligan’s take on the character is refreshing and bold, allowing The Riddler to not just be a “one-trick pony.” This at-times terrifying story is one of the very best Bat-books featuring the Riddler, and it remains the high watermark for reinventions of the character.

1 Tom King and Mitch Gerads Told The Definitive Riddler Story

Batman – One Bad Day: The Riddler

If seeing the Riddler forgo his usual methods of criminality in favor of more occult means was terrifying, then seeing him give up his clue-giving and riddle-leaving entirely is downright unfathomable. Tom King once again returns to the character of Edward Nygma in this attempt to give the character a “Killing Joke-esque” definitive story — and it certainly delivers on that promise. The DC Black Label Title depicts the Riddler committing a series of senseless crimes, though leaves no clues or riddles for Batman or the police to solve.

What follows is a deep-dive into the psyche of one of Batman’s greatest foes, as well as the Dark Knight himself. What would happen if one of Batman’s most brilliant enemies simply stopped providing a means of stopping him? A definitive, modern, fully-realized vision of the Riddler and his terrifying brand of villainy, One Bad Day: The Riddler is impossible to miss for any fans of Edward Nygma, Batman, or just plain old good comics.