Despite being one of Batman’s oldest foes, the Riddler remains one of the more underrated by the other members of his Rogues Gallery. He has no discernible physical strength and for all intents and purposes, he’s just super smart and good with riddles. He’s not overly psychotic (although he has those moments) and he’s definitely not that physically strong or imposing. For all intents and purposes, he’s just a smart guy who maybe loves a battle of wits a bit too much. Recently however, he was beaten and left for dead by Poison Ivy, who she too doesn’t fall far on the physical strength meter.
But when the guy is on, he can leave Batman stumped. When he’s off the rails, the Riddler is as much of a threat as anyone else is to Gotham. He knows Batman’s secret identity and has on several occasions been able to help the GCPD in catching some criminals that had even Batman flummoxed. He is usually a villain, though. No matter how much fans or other characters might underestimate him, in his over 70 years of existence, Edward E. Nygma has done some terrible things. Here are The 10 Worst Things The Riddler Has Ever Done.
10 The Riddle Of The Minotaur (Batman: The Animated Series)
Fans have praised the work of Kevin Conroy and Mark Hamill for their work on The Animated Series for years now. But the Riddler, voiced by the future Lionel Luthor, John Glover was no slouch either. He made three appearances during the show’s run, the first one is the most famous one - “If You’re So Smart, Why Aren’t You Rich?”
He kidnaps his old boss and locks him away in a live-action version of his game; "The Riddle Of The Minotaur.” While the Caped Crusaders save the day, Nygma’s old boss is left paranoid, sleeping with multiple locks and a gun under his bed, fearful that the Riddler might return.
9 Turned Elliot Against Bruce (Hush)
With a brain cancer diagnosis, the Riddler has acted fast to find a cure, which he did in the Lazarus Pits. He was able to deduce Batman’s identity and used a childhood friend, Thomas Elliot to construct an elaborate plot to mess with Batman from afar in an attempt to break him.
The Riddler succeeded in manipulating everyone but had failed to account for two things - one, the riddle of who is Batman would be a worthless riddle if ever solved and two, Ras Al Ghul would hunt Nygma down if he ever found out someone had used his Lazarus Pits.
8 Drugged Barbara (Thrillkiller)
The alternate universe Elseworlds story, Thrillkiller, features a real nasty version of the Riddler. The story takes place in a no-Batman, Gotham City circa 1961, the beginnings of the sexual revolution. Our heroes, Robin and Batgirl. After Robin’s death, Barbara Gordon goes to see a psychiatrist, Edward Nygma.
He keeps her dosed and doped up on a heavy supply of Valium and suggests that she go see other people. Alfred at the behest of Commissioner Gordon takes the drugs away, thinking Nygma’s a quack.
7 Murdering For Love (Gotham)
Gotham was one heck of a twisted prequel to the Batman story. Just about every future villain of the Caped Crusader showed up and was certifiable. Nygma was no different. He started working for the GCPD. But he quickly started to crack. He killed his crush’s abusive boyfriend and actually started dating Kristen Kringle.
Once she found out the truth, he killed her as well as she tried to alert authorities. While burying her, he wound murdering witnesses and buried them too.
6 Used Clayface To Torment Batman (Hush)
During the epilogue of “Hush,” it was revealed the Riddler was behind everything, cleverly manipulating everything behind the scenes. That means that just about everything was secretly his doing. But on particularly dastardly deed needs to be highlighted. At one point, all signs pointed to Jason Todd as Hush.
That was impossible since at this point, Jason was still very much dead. Seeing his murdered protege beating on him almost brought Batman to the core, until he realized that it was Clayface impersonating Jason the whole time.
5 Locked Batman In A Well (The Primal Riddle)
The Riddler has a penchant for all kinds of dangerous traps that double as physical riddles for his victims to attempt to find their way out of.
In the Legends Of The Dark Knight story, “The Primal Riddle,” Nygma manages to trap the Dark Knight down a pit that is taking in a lot of water on rather quickly. The sides are also electrified. Batman doesn’t necessarily solve this riddle per se, but he did find a way to short out the current and escape, enraging the Riddler.
4 Killed His Daughter (Gilded Lily)
Representing Titans East was Enigma. She would prove to be the Riddler’s daughter. She teams up with Joker’s daughter, Duela Dent (no relation to Harvey) were coincidentally hired by Two-Face’s wife, Gilda to find her hubby’s coin from the Falcone’s in the story, “Gilded Lily.”
During the events of the story, she calls her father a has been. He responds with a riddle - “what’s green and purple and bleeds profusely?” Before beating the ever-living crap out of her, leaving her (presumably) for dead.
3 Invaded Bruce’s Mind (Batman Forever)
The Riddler has had plenty of big-screen moments, none more prominent than when Jim Carrey brought Edward Nygma to the big screen in Batman Forever. Here, as The Riddler, Carrey added his unique brand of dark comedy to the role.
During the movie, The Riddler was able to use his machinery to invade Bruce’s mind and learn his secret identity. That led to him and Two-Face invading and blowing up the Batcave.
2 Put A Bomb On Catwoman’s Neck (Arkham Knight)
The Arkham video games are among the best superhero games around - they truly put you in the mood of being Batman. Each game has hundreds of challengers to conquer get Riddler trophies and unlock bonuses.
In Arkham Knight, the past time is no different, except that he’s got bomb strapped around Catwoman’s neck and he’s got to complete the challenges to get the keys to unlock the collar. Succeed in freeing her, and the duo winds up having to fight the Riddler in a giant mech suit.
1 Brought Gotham To Its Knees (Savage City)
The Riddler was able to bring Gotham City to its knees by blowing up the reservoirs and flooding the city. With most power cut off from the city, the Riddler gives Batman an easy fix to turning the lights back on.
He has to hook himself up and electrocute himself to jumpstart the power in Gotham. No riddles, just sadism from a guy who nearly had Batman and his city beat.
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