The main antagonist ofThe Batman , the Riddler has always been treated as C - list baddie . 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 perish through many different incarnations and styles over the decades .

Since his debut in 1948 , Riddler has been portrayed as a puzzling juvenile delinquent to a vehement sequential killer to even a reform anti - hero . With so many comic , it can be scare off for newcomers to the character to foot , but here is a selection of the Riddler ’s most iconic topic and stories of the past .

Detective Comics #140

It ’s as good of a place to start as any . The Riddler debuted inDetective Comics # 140and was created by Bill Finger , the creator of Batman himself . It show the rootage of Edward Nigma as he germinate his Riddler persona to take on Batman , losing sake in swindling intermediate citizen .

It ’s one of the rare time where a villain ’s quest commence and ends with Batman . Though he causes hassle for all of Gotham , his fixation is with Batman in the end . It all began with this comedian and anyone concerned in the Riddler should check it out and see whereone of Batman ’s first villains began .

Secret Origins Special #1

This one - shot secernate well - crafted tale for multiple of Batman ’s rogues . One of the account is about the Riddler telling his lifespan tarradiddle to reporters ; give a more   self-examining   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 wooing rather than a skin - tight unitard . A standardized design was first introduced by Frank Gorshin ’s   Riddler   in the 1966Batmanseries .

Batman: Run, Riddler, Run

When a private security measures force aptly titled Perfect Security arrives to make job for Edward Nigma , the villain end up having no choice but to partner up with Batman . That alone is one of the big appeals to the comedian , as it is always quite a survey to see Batman teamed up with one of his foes .

While the artwork in this issue has much to be want , the overall concept is executed well with a nice portmanteau word of action , suspense , and comedy . The comraderie between Batman and Riddler is unique and it help showcase that Riddler is more than just a one - trick villain .

The Riddler: Year Of The Villain

Superman ’s iconic   challenger Lex Luthor has given endowment to the well of the dear supervillains of the DC universe as part of " The Year Of The Villain " case . One scoundrel was not   on   that list of recipients : Edward Nigma . Of course , the Riddler does n’t take this well and becomes determined to find out why .

This comic plays with expectation , making the reader think it ’s expire to go one way but goes in a far dissimilar direction . It lead to another character study of the Riddler as he delves more into his past , peculiarly his childhood . It also ends on a very unexpected greenback that shows some character growth .

Gotham City Sirens #9

Paul Dini is look at one of Batman ’s best writersand he is one of the wizardry behindBatman : The Animated Series . So it makes sensory faculty that when the Riddler is allied with the Gotham City Sirens , Dini ’s style skin as if it was a comic base on the animated show .

Mixing dingy bodily fluid with a police detective thriller , the Gotham City Sirens hire Edward Nigma to help them reset the case of a numb body crash into their office .   Edward has to consider with the wildness of all three anti - heroes ' personality while attempt to uncover the whodunit , which makes for an enjoyable floor from his linear perspective .

Batman: The Long Halloween #7

There are a lot of suspect as to who the   murderer known as Holiday is .   So much so that the Riddler is institute in to peradventure figure out the mystery behind this unusual sequential killer . He presents many dissimilar suspect but he does not give a unequivocal answer .

This part of the famous chronicle , The Long Halloween , depict Riddler less as a mastermind and more akin to a swindler . However , it is a creepier take on the character which is meet for this more detective noir thrillerthat help enliven Matt Reeves’The Batman .

Batman: Dark Knight, Dark City

Those look for a much darker take on the Riddler   akin to Paul Dano ’s version   should foot upBatman : Dark Knight , Dark City . Riddler makes Batman take part in a supernatural rite that helps pave the way for other supernatural story such asJustice League Dark , which was also write by Peter Milligan .

Not only is it a different story for the Riddler , but it ’s a different narration for Batman , dealing with rather grisly murders as well as a hellish cult that colligate back to a story in the past . Dark Knight , Dark Cityhas the Riddler at likely his most depraved , especially with how he manipulates Batman .

Batman: Zero Year

With the New 52’sZero class , buff get to see revamps for many dissimilar villains as it search a newer take on Batman ’s first twelvemonth . One of them was the Riddler , who was less of a amaze trickster and presented more as a serious domesticated terrorist and egomaniac .

Zero Yearis the staring take on the Riddler for those wanting to see the character taken in a unlike direction;it almost ferment the Riddler into Batman ’s greatest foe . It ’s also one of the few times Riddler ’s story lease place over multiple consequence 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 conundrum of the story . This write up that can also be witness inBatman : Arkham - The Riddlerfocuses on Batman trying to visualize out why Riddler is in lockup . It all starts with a riddle : " What have I got in my pouch ? " In reference to the noted Bilbo Baggins and Gollum sequence inThe Hobbit .

This leads Batman on a short but sweet lilliputian prank ( with stunning art by Dennis Calero ) with a   wrench that very few might expect . It also portray 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 straight than usual . This is when he became E. Nigma , Consulting Detective who used his huge intelligence to serve people rather than engage his obsession .

Detective Comics # 822had the Dark Knight teaming up with his x - villain on a case . It ’s one of many   representative   that demonstrates that many of Batman ’s villain could have become dear heroes , just as he is . Riddler makes for a play investigator to stick with in Gotham City ,   and it is a pity that it did n’t last forever .

NEXT:5 Times Villains Made Great Heroes ( & 5 Times They die )

Comic book art: Batman faces the four Robins: Nightwing Dick Grayson, Red Hood Jason Todd, Red Robin Tim Drake, and Robin Damian Wayne.

Comic book art: batman by arkham asylum

Collage of Willow and Clash of the Titans

Split image of Batman confronting Riddler in Batman Zero Year and Riddler smirking up at the ceiling in Batman Arkham - The Riddler

Comic book art: The Riddler capturing Batman and Robin in cover artwork for Detective Comics #140.

The Riddler telling his story to reporters in Secret Origins Special 1

Batman speaking with the Riddler in Batman Run Riddler Run

Riddler complaining to Lex Luthor in Riddler Year Of The Villain

Riddler gathering information about the case from the Sirens in Gotham City Sirens #9

Comic book art: The Riddler wielding a pistol in Carmine Falcone’s office in Batman The Long Halloween.

Riddler threatening the life of a police officer in Batman Dark Knight, Dark City

Batman and Riddler facing each other in Batman Zero Year

Riddler speaking with Batman in his cell in Riddler In The Dark of Batman: Arkham - The Riddler

Edward Nigma inside the Batmobile chatting with Batman in Detective Comics 822

Batman