The Riddler Crash Course

Jordan Edwards crashes the gates to help you solve some of The Riddler’s puzzles and what to read to learn more about the human enigma.

Crash Courses are designed as an introduction to different topics and where to go next if you enjoyed them! If you want to know more about the series, check out our introduction.

Let’s talk the Riddler. With the release of The Batman, it’s as good a time as any, right? If you’re excited to see Paul Dano’s take on the character in the film and want to know more about the character, hopefully I can be of some help. Riddler has long been one of my favourite Batman rogues. A villain with a unique and incredibly interesting motive; to prove that he is smarter. The great thing about Riddler is his incredible ego. He thinks he’s a genius and he certainly has the credentials to prove it. He’s a character who constantly wants to show you just HOW intelligent and clever he is. He’ll rob a bank, but not without lauding over you with the question of how he did it. Of course, there is one character who always knows how he does it, and therein lies the fun of Batman and Riddler’s rivalry. Riddler wants to test Batman to see how smart he is and in doing so, prove he’s above him and worthy of praise. He’s loud, boisterous and seeking attention, which just always makes him a captivating presence. So if you’re wanting to dig into the mind of Gotham’s greenest and meanest egomaniac then look no further. These suggestions are, in my mind, the prime material for The Riddler. There’s something here for newcomers wanting to get into the character and veterans looking for something new! I hope you enjoy this selection and come out the other side just a little smarter. 

The Bread: 

If You’re So Smart Why Aren’t You Rich? – Batman the Animated Series Season 1 Episode 40: 

Batman: The Animated Series is pretty much the best introduction for most Batman characters and Riddler is no exception. Riddler was a later addition, though, and used a whole lot less than other villains. While Joker, Penguin, and Two Face were often featured together and had numerous episodes, Riddler wasn’t introduced until the show’s  40th episode. Regardless, this episode is a brilliant update of the character. Here, Riddler is a Software designer gone rogue who threatens his former boss and eventually draws Batman and Robin into a massive all-expansive game. The Riddler is, more so than any other Batman villain, a character who loves games. For him, the thrill isn’t in profit and he has no malicious intent. He simply wants to test people and prove himself. This episode understands that perfectly and puts that on full display. It’s a great showcase of the character and an origin that will set you up wonderfully for understanding the character more. 

Zero Year – Batman Vol 2 #21-33:

If one is wanting to learn more about the Prince of Puzzlers, Batman: Zero Year is an easy first recommendation. Zero Year was a 12-issue story detailing a new rebooted origin for Batman. It’s part of Scott Snyder and Greg Capullo’s incredible run and this story is my absolute favourite of theirs. The Riddler essentially holds Gotham City hostage to test their wits and intelligence. So Gotham has been turned into a rotting, overridden hellhole, well more than usual. It’s akin to a post apocalyptic Batman story where Riddler controls the entire city. It’s the highest stakes the Riddler has ever had and it’s a great showcase of his arrogant intellect and is the most desperate Batman has been to beat him. The craft on display from the entire creative team makes it just a stunning read. It has a very adventurous and pulpy tone which is matched up with the vibrant and zany colouring. For a starting Riddler comic, you can’t do any better.  

Solitaire – Batman Vol 2 #23.2:

When I do lists like these, I try to diversify and cast a wide net. I don’t want to recommend stuff that is just gonna be too samey and I don’t want to just recommend the works of the same people over and over. Sometimes though I make exceptions, like with Batman #23.2, another Riddler story written by Scott Snyder. This time, however, it’s a short one and done issue focusing on the Riddler. The set up is simple; Nygma is breaking into his old office at Wayne Enterprises. The story follows two perspectives: Nygma, of course, but also a lone heroic security guard aiming to take him down. The reason I have this here is because it just brilliantly encapsulates a specific aspect of his character; his pettiness. The issue reveals what he has broken in for and it’s emblematic of his spiteful narcissism. It also helps that it’s just a brilliantly executed one shot with a great heist element. A whole lot of fun. 

The Meat: 

War of Jokes and Riddles –  Batman Vol 3 #25-32:

The War of Jokes and Riddles is a major stand out in Tom King’s run on Batman. This story follows on perfectly from Zero Year since this is set during Batman’s second year as Gotham’s protector. Essentially it centers on a gang war waging through the city fought between Riddler and Joker. The rest of Gotham’s villains side with one or the other and chaos breaks out. Gotham becomes a war zone with supervillains and criminals openly fighting in the streets. At the heart of the story is an incredibly petty rivalry. Joker seems to have lost his sense of humour and no longer finds anything funny. The Riddler is similarly unsatisfied because his biggest Riddle, Batman, cannot be solved. So essentially, it’s a massive gang war over who has the right to kill Batman. It’s really silly and action packed while also examining the relationship that Riddler has to his arch-nemesis. 

E.Nygma Consulting Detective – Detective Comics #822:

In the 2000s, writer Paul Dini took Riddler in a fresh and exciting direction. Riddler was pardoned of all crimes and decided to take on the role of a private detective. ‘E.Nigma Consulting Detective’ follows Batman as he reluctantly has to work alongside him as an uneasy ally. This is essentially the return of an idea set up in 1982, but not properly expanded upon. It’s a brilliant enough set up on it’s own but the story that Dini weaves here manages to match it. Riddler and Batman are working together but also silently and politely competing, one upping each other while working to the same goal. Both are geniuses who know their way around Gotham but their push/pull dynamic means they struggle to stay on the same page. If after watching The Batman you want a hard boiled detective story, then I can’t recommend this enough. 

(Bonus recommendation: For a similar story but with a more lighthearted tone check out Batman Confidential #26-28) 

Batman 66 – High Diddle Riddle/ Smack in the Middle:

Ol’ Eddie Nygma had the privilege of being the villain for the first two episodes of the 1966 Batman show starring Adam West and Burt Ward. These two episodes set the template and formula for this foundation of popular culture. Thankfully it also stands up as a great showcase for Riddler. The character was played by two actors over the show’s run but the original is still the my favorite. Frank Gorshin’s Riddler was manic, totally insane and absolutely captivating to watch on screen. He’s clearly having the time of his life with this character and that joyfulness helped to define the character in the comics as well. This episode has the brilliant premise of the Riddler framing and then suing Batman. It’s a total riot and still holds up beautifully. There is a lot of great Riddler stuff in ‘66 so start here and keep on watching. 

The Special Sauce: 

Dark Knight Dark City – Batman Vol 1 #452-454:

Peter Milligan in the 90s wrote a bunch of different Batman stories and one such story was Dark Knight Dark City. This was a wonderful little mini series with art by Kieron Dwyer. Now most Batman stories are dark and gothic but Milligan and Dwyer take it to a whole other level here. This is one of the weirdest and most out there Batman stories ever published. Essentially it lays down some lore for Gotham surrounding the Bat god Barbatos (something future Bat writers Grant Morrison and Scott Snyder would run with). It’s a dark occult story dealing with Gotham’s dark roots, human sacrifice, ancient rituals, all that jazz. But it’s also weirdly a Riddler story, although a MUCH darker one. He’s far more vicious and cruel here than almost any other incarnation. So I recommend it only for those who really want to read all there is with the character because the character from the Silver Age this is not. Which might be a turn off for many but if you want to see a unique and more twisted take on the character, Dark Knight Dark City is a good one to read. 

Riddlers Romance – Question Vol 1 #26:

This choice doesn’t come from a Batman comic at all. In fact it comes from a character who honestly makes more sense for Riddler to go up against: The Question. Who better to answer riddles than a detective character literally called The Question. Riddler popped up in #26 of Dennis O’Neil’s run on the character. This issue follows Riddler as he’s broken out of prison by an infatuated admirer, the character of Sphinx. The two of them hold up a bus and it’s up to Question to stop them. What’s great about this story is seeing Riddler in a different context. He’s not playing the hits and fighting Batman, he’s vastly out of his element in a different scenario. This also plays wonderfully into the art as Bill Wray portrays him as more weasley and pathetic. He’s in a different, more violent world now, far outside the familiar Gotham. It’s a neat one and done story that shows us more of Riddler’s character outside of his element. 

The Riddle – Batman Black and White #5:

The Riddler as a character lends himself to experimental stories. He’s all about games, puzzles and thinking outside the box. But very few of his stories are all THAT experimental. So that’s why this story was such a joy when it came out a little while ago. This is ‘The Riddle’ from Batman Black and White, an anthology series with a black and white motif. But the real kick of this story is that it’s a choose your own adventure comic. Batman chases Riddler into a maze and you as the reader have to work your way through the puzzle. It’s a really smart and clever angle for a Riddler story. It helps that it’s also just an incredibly funny comic with great comedic writing. Which brings me to the fact that this has the all time great creative team of Kieron Gillen and Jamie McKelvie. Yep, the creative team behind the Wicked and the Divine did a funny choose your own adventure comic. It’s as good as it sounds. 

When is a Door – Secret Origins Special Vol 2 #1: 

The other short story is a classic from Secret Origins Special Vol 2 #1. It’s written by freaking Neil Gaiman with a cartoony and melancholic art style by Bernie Mireault. Now the plot of this is mostly inconsequential. Riddler is being interviewed by a TV crew in an exhibit of massive props and sculptures. So, Riddler is talking to the interviewers but really, he’s talking to us, the readers. This is an incredibly meta comic that reflects on the changing state of comics, especially Batman comics. Riddler as a character has often struggled to keep up with other Batman villains as they got darker. He’s a very old school character, focused on clever puzzles and traps, not turf wars and murders. So this story is Gaiman’s way of examining that. It’s a sweet and very melancholic story of Riddler reckoning with this changing Gotham and changing industry. It’s sad but a brilliant ode to one of the few supervillains who is often still truly silly.

Leave a Reply