Riddle Me This: what are some of the best Riddler stories?

The Riddler is one of the most easily identifiable members of Batman’s rogues gallery.  Ask anyone to name three or four Bat villains and dear old Edward Nygma (or Nashton) is bound to come up more often than not.  He’s also one of the most notoriously difficult characters to write, as many acclaimed creators have admitted.  After all, devising believable riddles that would stump the Caped Crusader is no mean feat.  It’s why there weren’t many episodes of Batman: The Animated Series that focused solely on Nygma’s schemes (though the limited amount we have are generally high quality and immensely memorable.)

With the inspired and genius casting of Paul Dano as Edward Nashton (which, yes, has comics precedence) in Matt Reeves’ upcoming The Batman film, we’ve been asked by a reader to name some of the best Riddler stories for those who aren’t as familiar with the king of conundrums.

So, I did.

Keep in mind that this list is by no means exhaustive, nor should it be seen as a definitive ranking.  In fact, I’m not even going to compare these stories to each other.  Some I’d read before, some have received great acclaim and I’m coming to for the first time, and at least one I just happened to stumble across on DC Universe.  There are also some notable omissions: while there’s some pretty fun Riddler stuff in The Long Halloween, the overall story isn’t about him, so I didn’t include it (and it’s not like we need another Long Halloween recommendation out there anyway), and while he is featured prominently in Hush… well, you know how I feel about that one.

Anyway, without further delay, here are some great Riddler stories you and your loved ones should check out.

Detective Comics 140 - Best Riddler Stories

Detective Comics #140: “The Riddler”

We have to start somewhere, so why not the beginning?  Detective Comics #140 was indeed the first appearance of the Riddler, and sixty years later it still holds up remarkably well.  It tells the origin of the Riddler, who began as a young man who fancied himself smarter than everyone else, so he tried to prove it the best way he knew how: by cheating.

What’s best about this story are the crazy puzzle-themed items and death traps that Riddler uses to foil the Dynamic Duo.  He broadcasts his first riddle using a giant crossword puzzle, delivers his second via a giant puzzle, and slowly ensnares a hostage in… yes, you guessed it: a giant wire trap.  It all leads to a climax in a giant glass maze that is genuinely thrilling to this day, so it’s easy to see why the Riddler became one of Batman’s greatest foes.


This issue can be found in Batman: The TV Stories, which also contains the equally great– and perhaps even more important– Batman #171, “The Ruse of the Riddler”.  You can read Andrew’s review of both here.

Batman: Dark Knight, Dark City - Best Riddler Stories

Batman: Dark Knight, Dark City

This is one that I considered omitting, not because it’s bad, but because it’s a book that has really hit a renaissance in recent years.  Still, it’s not at the level of notoriety as something like Zero Year or Hush, so here it stays.

What’s most notable about Dark Knight, Dark City is that it’s a horror comic.  Originally running from Batman #452-454, the arc was written by Peter Milligan, illustrated by Kieron Dwyer, and had appropriately spooky covers from Mike Mignola.  Where the Riddler was originally seen as nothing more than a clownish buffoon with delusions of grandeur, Milligan recast Nygma as a rather bloodthirsty obsessive who decides to recreate a supernatural ritual.  It’s disturbing and fairly gruesome, introducing Barbatos (here “Barbathos”) long before the days of Metal, yet still stays “on brand” with the Riddler’s modus operandi.

This arc can be found on DC Universe or purchased on ComiXology.  You can read Andrew’s original review here.

Batman Adventures 10 - Best Riddler Stories

The Batman Adventures #10: “The Last Riddler Story”

Given the chance, I will always talk about The Batman Adventures.  Based on Batman: The Animated Series— which is pretty much everyone’s favorite Batman thing, or at least in the top five– The Batman Adventures was a series of comics for readers of all ages that were almost consistently the best Batman comics on the stands.

And this was during Knightfall, the early days of Robin titles, and tons of other great Batman content.  Yes, they are that good.

“The Last Riddler Story” is exactly what it sounds like: the supposed end of Edward Nygma’s career as a criminal.  Weary of constantly being bested by Batman, Nygma decides to hang up the dope green jacket and sick question mark cane.  The condition?  Batman has to solve one last riddle.

The team of Kelly Puckett, Mike Parobeck, and Rick Burchett  is, hands down, one of the best Batman creative teams of all time, and their work here is just seamless in its simple perfection.  The late Parobeck is a sadly underrated artist, and Puckett wrote scripts that worked just as well on the printed page as they would have on a TV screen.  What’s best about this story is that they subvert expectations, making the Riddler win even as he loses.  It’s a great, great story no matter how you look at it.

This story can be found on DC Universe of purchased on ComiXology.  You can read my review here.

Detective Comics 822 - Best Riddler Stories

Detective Comics #822: “E. Nigma, Consulting Detective”

This one was a blind-spot for me for years, though I’d heard great things: Paul Dini (one of the geniuses behind Batman: The Animated Series) writing a story where the Riddler fights on the side of angels as a consulting private investigator?  Sold.

So yeah, I read it for the first time the other night, and it’s pretty good.  The concept itself is just brilliant, and a clever twist on Nygma’s psyche and motivations.  I mean, why wouldn’t he “reform” and solve mysteries just to flaunt his mental superiority over Batman?  That’s amazing.

The biggest detriment to the story is that it didn’t last longer, which is a shame because the idea has legs.  Still, Dini’s script mostly holds up, and there’s great work from Don Kramer, Wayne Faucher, John Kalisz, and Jared K. Fletcher, and it was in that era when Simone Bianchi was doing those eerily realistic, ultra-stylized covers.  Give it a shot if you’ve never read it before.

This story can be found on DC Universe or purchased on ComiXology.

Batman 362 - Best Riddler Stories

Batman #362: “When Riddled by the Riddler…”

Now this is one that I just stumbled upon.  By typing in “Riddler” on DC Universe, this was one of the first results that I wasn’t familiar with, so I decided to give it a shot.  It’s not a hall of famer or anything, but it’s plenty of fun and a time capsule of an era of comics I kind of wish we could go back to.

Written by Doug Moench, illustrated by Don Newton, inked by Alfredo Alcala, colored by Adrienne Roy, and lettered by Ben Oda (all overseen by editor Len Wein), I’d be kind of disappointed if you didn’t check it out based on the pedigree alone.  The Riddler, see, has gotten loose again, and of course it’s up to Batman and Commissioner Gordon to solve the case.  There are some fairly silly riddles that lead Batman to a Mother Goose theme park and to the set of a game show, and an overall sense of levity that makes it a joy to read (Gordon has an absolutely brilliant line that cracked me up: “Dissatisfied with such small pickings– and convinced he was some kind of conundrum champion– he decided to commit puzzle crimes in a duel of wits with the law.”)

Puzzle.  Crimes.


It’s not all goofiness, though, because Gordon is actually at the center of an internal investigation that is being headed by Harvey Bullock, at the behest of Mayor Hill.  There’s quite a bit of the issue that’s devoted to this subplot, and even though we aren’t given too much context, these scenes never feel confusing or drag the story down.  In fact, I feel they do the opposite, as they emphasize something I love about comics of this era: they all feel like they’re part of an ongoing story, and the characters feel like they have lives outside of what we see on the page.  The events of a single issue serve the wider reach of the title, rather than the other way around.  These one-and-done stories feel more complete and part of something bigger than themselves, as opposed to modern stories that are written to fit into a trade.  Even though a single story might be longer these days, they in turn feel smaller without having a ton of connective tissue between each installment that doesn’t serve the story at hand.

The best endorsement I can give for this issue?  I had to fight myself to keep from reading the next one, because I had such a great time diving into this oft-overlooked era.

This story can be found on DC Universe or purchased on ComiXology.

Batman 66 1 - Best Riddler Stories

Batman ‘66 #1: “The Riddler’s Ruse”

And no list of Jay’s would be complete without Batman ’66, now, would it?

Mirroring the absolutely brilliant and amazing television show after which it’s fashioned, the first issue of the digital-first series is all about the Riddler and his attempts to… you know what?  It doesn’t even matter.  This entire comic series was incredible, and it kicked off with a bang.  Jonathan Case nails the aesthetic of the show, and his Riddler looks more like Frank Gorshin than Frank Gorshin himself.  Jeff Parker’s writing is spot-on with the tone of the series, as the villains are larger than life, Robin is excitable in his exuberant enthusiasm, and Batman is a by-the-book lame-o square.  If you can, get the digital copy, which makes great use of the “animated guided view” in ComiXology.

This story can be found on DC Universe or purchased as an individual issue or as part of the Batman ’66 Vol. 1 collection on ComiXology.  Read Andrew’s original review here.

A few Honorable Mentions:

Batman: “Hi Diddle Diddle/Smack in the Middle”

Frank Gorshin’s Riddler was the villain for the Sixties Batman television series, portraying the character with a manic glee that was as campy as it was terrifying.  So influential and memorable was his performance that it went on to influence an entirely different character, as modern interpretations of the Joker hew closer to this portrayal than they do Cesar Romero’s (equally great) Clown Prince of Crime.

The show debuted with the two-part “Hi Diddle Diddle” and “Smack in the Middle,” which established the series’ camp tone that was… much closer to the comics of the time than you’d think.  This is where we were introduced to Burt Ward’s Robin and his “Holy!” exclamations, Adam West’s deadpan and straitlaced Batman, and iconic elements like George Barris’ Batmobile and the Batusi.

Hovering above it all was Frank Gorshin’s Riddler, clad in a green leotard and purple mask, leading a group of ruffians and an alluring moll in his criminal schemes.  For a show that was already big, the performance was larger than life, putting a stamp on the series and the character for all time.  He went on to portray the character for the rest of the show’s first season and the theatrical film, while John Astin appeared as the Riddler in season two before Gorshin once again played the role in the third and final season.

Which had an episode where he and Batman fought each other in a boxing match.  Solid runner-up.

Batman: The Animated Series: “If You’re So Smart, Why Aren’t You Rich?”

Finally, here’s the first episode featuring the Riddler from the seminal Batman: The Animated Series.  This one always stuck out to me as a kid because, hey, who wouldn’t want to take part in a life-size video game maze?  Flying around on that giant hand?  Awesome.

As great and clever as the episode’s main setpiece is, it’s John Glover’s portrayal of the Riddler that really sells it.  He begins as a brilliant programmer who creates a hit game, only to have his creation taken away from him so somebody else can profit from his work.  Now jaded, bitter, and angry, Nygma uses his brains to exact revenge on those who wronged him… and in the case of Batman and Robin, those who want to stop him.

Glover’s performance is one of the best in a series that’s made up of nothing but great vocal performances, absolutely nailing the smug and smarmy attitude of the Riddler as he talks down to everyone he deems lesser than himself.

Plus, I cannot stress this enough: his ensemble is fresh.  It just needs more question marks and it would be perfect.

So there you have it: some great Riddler stories.  As I said, this is not an exhaustive list, so sound off below: what’s your favorite Riddler story?