40 years ago - Edward Nygma is born to an abusive father.
27 years ago - 13-year-old Edward begins building and selling elaborate puzzles.
21 years ago - 19-year-old Edward, bored with stumping people with his puzzles begins to engage in a variety of thefts, leaving small riddles that confound any attempt to find the purpetrator.
15 years ago - 25-year-old Edward first learns about the newly active Batman. Offended at the implications of the idea of him being the "world's greatest detective", he feels compelled to challenge him, and begins planning his criminal career.
12 years ago - 28-years-ago Edward makes his debut as the Riddler, staging a grand ongoing crime spree pitting him against Batman in a elaborate game. Eventually, he is caught and put in Arkham.
10 years ago - 30-year-old Edward is released from Arkham. Now a known criminal, he creates his underground 'mystery theater', part live show and part internet sensation. His heists are hidden in plain sight, with no way to connect him to the crimes. He briefly partners with the Cluemaster only to leave him holding all the blame, getting away scott free.
9 years ago - 31-year-old Edward begins working as an information broker & freelance problem solver. He continues to stage his heists but they are designed to draw less attention.
5 years ago - 35-year-old Edward attempts his greatest heist, staging a massive reveal of Batman's secret identity. His plan is stymied by Oracle and he enfuriates the entire Gotham underworld, leaving him chased and tormented by many of Batman's enemies. He is almost killed by Pamela Isley. He winds up hiding with Oracle, and she manages to help him unlock some of the mysteries of his compulsion. He spends his entire fortune staging his most elaborate con ever, undoing his informant network & escaping the wrath of Gotham's underworld before he turns himself in.
3 years ago - 37-year-old Edward is forced to leave Blackgate during No Man's Land, continually playing different factions off each other. He turns himself in when the crisis is over and gives up key information that helps bring in many dangerous escapees. His sentance is commuted.
1 year ago - 39-year-old Edward is released from Arkham. He immediately makes back his fortune in what appear completely legitimate ways and sets himself up as a private detective.
The Riddler is very easily one of the most recognizeable baddies in Batman's villain's gallery, but he stands out from among all the other characters because unlike everyone else, he never really transitioned over into the new more psychotic, violent world of post-70's Batman. Of course, why SHOULD he? The Riddler is an iconic character thanks to his appearances in movies and tv, and he deserves to find a role that fits him, rather than trying to force him to be something he's not.
The Riddler's Comic History
The Riddler first appeared in 1948. He stood out among the various themed villains of the era because the readers were challenged to solve his riddles alongside Batman and Robin. He actually didn't show up again for another 17 years, but his reappearance in Batman #171 was actually used as the inspiration for the pilot episode of the 60's series, where he was played by Frank Gorshin with a certain madcap brilliance. and was quickly cemented as one of Batman's greatest villains.
He was so cartoonish and fabulous that you could argue that the Riddler was one of the best examples of Batman's early, family-friendly years. This is very likely why we started to see less of him after the early 70's when Neal Adams, Denny O'Neil and Julius Schwartz reimagined Batman in a much more grounded way. This was the enviornment that brought is Ra's Al Ghul and the notoriously violent Joker. Of course, the world of Batman became an even darker place in the aftermath of Frank Miller's Dark Knight Returns or the 1989 Tim Burton movie.
There have been a few attempts to redesgn the characer to fit into this new world, but there's really been only one that stuck, and it did so by firmly establishing just what part of Batman's history he belongs in.
Our Riddler Story
1989 saw the publication of a single issue called Secret Origins Special. it included three small stories by some really amazing writers and artists featuring three classic Batman villains. All of it is fantastic, but it features one story by the legendary Neil Gaiman that is very likely the best Riddler story ever written. The art is credited simly to "BEM", but it's actually done by Bernie Mireault, the artists often credited as a major influence for Hellboy creator Mike Mignola. Please go buy this comic, but for our purposes, please read this single page.
The monologue presented here is pretty clearly meant to break the fourth wall a bit. The characters aren't meant to be aware of these stylistic shifts in the story, but it DOES speak to the idea that the Riddler simply isn't part of the culture of violence that so many of Batman's enemies are using. He's a man who wants to prove his intellect, not to hurt anyone.
With that in mind, you get a notion of exactly what our version of the Riddler should be. We know that he's a genius, but that he has a very unhealthy compulsion to PROVE that he's a genius. The nature of his crimes is far less important.
Often the challenge with making the Riddler make sense is the fact that he's essentially leaving behind roadmaps to his location. How seriously can you take a criminal that is ASKING to be caught? The answer to that problem isn't an easy one, because the solution is just to write better Riddles. Bruce Wayne and Edward Nygma need to be like Sherlock and Mycroft. The mental challenges need to be truely genius; that's where he becomes a fascinating and wildly entertaining character.
There's also the fact that Edward is often willing to cheat. The truth is, Bruce is smarter than Edward. He is obsessed with being the smarter of the two of them, but he's NOT, and that torments him. We deliberately kept him from ever engaging in the same scam twice because he's constantly looking for the way he will finally prove his superiority.
There was a period in the comics where Edward actually turned over a new leaf and became a private investigator. Many of Batman's baddies have done that in one way or another but it really fits Edward well, because he can keep right on doing the one thing he REALLY wants to do; competing with Batman. He's obviously going to still be cheating, and no one could or SHOULD trust him, so you're not really losing anything by making that change, but you are getting a totally new and totally unique element to Batman's world, and that's just fantastic.
We really leaned into the process of his turning over his new leaf, making it take years even while he's in prison, and created the story of his greatest con that actually incorperates Barbara Gordon, the one member of team Batman most likely to give him a chance. In the end, we get a really great take on a classic character.
The Riddler's Costume
The Riddler as invented wore a green skin tight jumpsuit with purple trim and question mark details. This was also worn by Frank Gorshin when he played the character on the live TV show, but Frank fameously hated it and constantly asked for a new costume. He was eventually given what was essentally a green business suit with a bowler hat. The comics essentially ignored this costume until the aformentioned Secret Origins Special. Once he was depicted in his green and purple suit that one time they basially never went back, and it became he go-to costume.
Interestingly, the idea of him carrying his questionmark cane was actually introduced in the same issue, but it DIDN'T catch on until Jim Carry carried a similar cane in the Joel Schumacher movie. After this it became his standard accessory.
Different artists have different takes on just how he wears the suit, but I happen to like it when he is being deliberately dapper. He should look like a classicly dressed thin man type of character; as though all the physicality of the normal Batman villain is beneith him. He wants to project an image of someone far smarter than the rest of the world, and this is absoluely that look.
The Riddler's Future
Whenever you write a story of a classic villain turning over a new leaf it's understood that it's only a matter of time before they're back to their old ways. In our current timeline, Two-Face is currently in the middle of his rehabilitation, but we've understood that he's eventually going to fall again.
Riddler, however, I think is actually at his best in his new role as a private investigator and RIVAL of Batman rather than as his enemy. There has been attempt after attempt to craft a version of Riddler that fits into the larger tapestry of bad guys and while some of them have been more entertianing than others none of them have been so fresh and interesting as the idea of him simply being a detective in Gotham that's kind of an asshole.
There are SO many narrative ideas that we can deploy from here. He's never, ever looking out for anyone but himself, and his sole motivation is to be percieved as the smartest man in Gotham. Villains can come to him and he can pretend to rejoin them, only for him to eventually turn on everyone. Heroes can begrudgingly come to him for help they can get nowhere else and he can collect favors. What other villain operates in plain view without any illusion of wrongdoing, and who else could manage to make that entertaining?
It's a wonderful place to take this rellic of an earlier era of comics and let him be what he is.