The main antagonist of The Batman, the Riddler has always been treated as C-list villain. However, he's actually one of Batman's most iconic foes, which is why fans are happy to see him as the main threat. In the comics, the Riddler has gone through many different incarnations and styles over the decades.
Since his debut in 1948, Riddler has been portrayed as a puzzling delinquent to a violent serial killer to even a reformed anti-hero. With so many comics, it can be daunting for newcomers to the character to pick, but here is a selection of the Riddler's most iconic issues and stories of the past.
Detective Comics #140
It's as good of a place to start as any. The Riddler debuted in Detective Comics #140 and was created by Bill Finger, the creator of Batman himself. It shows the beginning of Edward Nigma as he develops his Riddler persona to take on Batman, losing interest in swindling average citizens.
It's one of the rare times where a villain's quest begins and ends with Batman. Though he causes trouble for all of Gotham, his obsession is with Batman in the end. It all began with this comic and anyone interested in the Riddler should check it out and see where one of Batman's first villains began.
Secret Origins Special #1
This one-shot tells well-crafted stories for multiple of Batman's rogues. One of the stories is about the Riddler telling his life story to reporters; giving a more introspective tale rather than a spectacle against the Caped Crusader.
It reveals that his real name is Edward Nashton, and it is one of the first comics to have Riddler wearing a green suit rather than a skin-tight unitard. A similar design was first introduced by Frank Gorshin's Riddler in the 1966 Batman series.
Batman: Run, Riddler, Run
When a private security force aptly titled Perfect Security arrives to cause problems for Edward Nigma, the villain ends up having no choice but to partner up with Batman. That alone is one of the biggest appeals to the comic, as it is always quite a sight to see Batman teamed up with one of his foes.
While the artwork in this issue has much to be desired, the overall concept is executed well with a nice blend of action, suspense, and comedy. The comraderie between Batman and Riddler is unique and it helps showcase that Riddler is more than just a one-trick villain.
The Riddler: Year Of The Villain
Superman's iconic rival Lex Luthor has given gifts to the best of the best supervillains of the DC universe as part of "The Year Of The Villain" event. One villain was not on that list of recipients: Edward Nigma. Of course, the Riddler doesn't take this well and becomes determined to find out why.
This comic plays with expectations, making the reader think it's going to go one way but goes in a far different direction. It leads to another character study of the Riddler as he delves more into his past, especially his childhood. It also ends on a very unexpected note that shows some character growth.
Gotham City Sirens #9
Paul Dini is considered one of Batman's best writers and he is one of the geniuses behind Batman: The Animated Series. So it makes sense that when the Riddler is allied with the Gotham City Sirens, Dini's style shines as if it was a comic based on the animated show.
Mixing dark humor with a detective thriller, the Gotham City Sirens hire Edward Nigma to help them solve the case of a dead body crashing into their office. Edward has to deal with the wildness of all three anti-heroes' personalities while trying to uncover the mystery, which makes for an enjoyable story from his perspective.
Batman: The Long Halloween #7
There are a lot of suspects as to who the murderer known as Holiday is. So much so that the Riddler is brought in to possibly solve the mystery behind this strange serial killer. He presents many different suspects but he does not give a definitive answer.
This part of the famous story, The Long Halloween, depicts Riddler less as a mastermind and more akin to a swindler. However, it is a creepier take on the character which is fitting for this more detective noir thriller that helped inspire Matt Reeves' The Batman.
Batman: Dark Knight, Dark City
Those looking for a much darker take on the Riddler akin to Paul Dano's version should pick up Batman: Dark Knight, Dark City. Riddler makes Batman take part in a supernatural ritual that helps pave the way for other supernatural stories such as Justice League Dark, which was also written by Peter Milligan.
Not only is it a different story for the Riddler, but it's a different story for Batman, dealing with rather grisly murders as well as a demonic cult that connects back to a story in the past. Dark Knight, Dark City has the Riddler at probably his most depraved, especially with how he manipulates Batman.
Batman: Zero Year
With the New 52's Zero Year, fans got to see revamps for many different villains as it explored a newer take on Batman's first year. One of them was the Riddler, who was less of a puzzling trickster and presented more as a dangerous domestic terrorist and egomaniac.
Zero Year is the perfect take on the Riddler for those wanting to see the character taken in a different direction; it almost turns the Riddler into Batman's greatest foe. It's also one of the few times Riddler's story took place over multiple issues rather than a one-off.
Legends Of The Dark Knight 100-Page Super Spectacular #2
Why would the Riddler turn himself into the GCPD? That's the riddle of the story. This story that can also be found in Batman: Arkham - The Riddler focuses on Batman trying to figure out why Riddler is in lockup. It all starts with a riddle: "What have I got in my pocket?" In reference to the famous Bilbo Baggins and Gollum sequence in The Hobbit.
This leads Batman on a short but sweet little caper (with stunning artwork by Dennis Calero) with a twist that very few might expect. It also depicts Batman and Riddler on more respectable terms, where they seem to think of each other less as mortal enemies and more as friendly rivals
Detective Comics #822
It might seem impossible, but there was a time that Riddler did go straight, or at least straighter than usual. This is when he became E. Nigma, Consulting Detective who used his vast intelligence to help people rather than pursue his obsession.
Detective Comics #822 had the Dark Knight teaming up with his ex-villain on a case. It's one of many instances that demonstrates that many of Batman's villains could have become beloved heroes, just as he is. Riddler makes for a fun detective to follow in Gotham City, and it is a shame that it didn't last forever.