Top 10 Darkest Riddler Moments

#10: Making Catwoman Wear an Explosive Collar

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“Batman: Arkham Knight” (2015) When Riddler wanted to get the dark knight’s attention, the villain decided to put Catwoman’s life in danger. Batman soon discovers that she’s wearing an explosive device that could go off if he made one wrong move. The only way to remove it safely is to solve all of Riddler’s devious puzzles. While forcing the Bat and Cat to play deadly games that would make Jigsaw jealous is bad, his motivation for risking Selena Kyle’s life is the worst part of this evil plot. Riddler just wanted to get back at Batman for past humiliations. Although the villain could’ve come up with any other revenge plot, bringing in Catwoman was cruel and unnecessary. Luckily, the pair beat his games and got serious payback.

“Batman Forever” While Jim Carrey’s Riddler could certainly be silly at times, he nearly got away with a very dark crime. After he deduces who Batman is, the villain teams up with Two-face, breaks into Wayne manor and captures Bruce’s love interest Chase Meridian. Riddler waited until Robin was also in his clutches before asking the Dark Knight to choose which good person lives or dies. The villain would’ve gladly seen either person fall to their doom just to make Batman suffer. And even though the dark knight figures out a third option, Robin still came extremely close to a brutal end. In one scene, Carrey proved that his Riddler was just as cutthroat as any version of the antagonist you’ve seen before.

“Question Vol 1 #26” (1989) Shortly after being released from jail, the Riddler meets a woman named Spinx on a bus. When she reveals her desire to rob and wound passengers on a bus, he doesn't try to stop her. The Riddler instead agrees to ask passengers riddles while Spinx holds innocent people at gunpoint. A wrong answer leads to instant death. Although Riddler doesn't hold the gun in this comic, he practically pulls the trigger by going along with his partner’s twisted game. Thankfully, the costumed Question intervened and saved everyone. But it’s terrifying to think of how many people might’ve perished if the hero wasn’t around to stop Nygma from asking riddles.

#7: Permanently Traumatizing His Boss

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“Batman: The Animated Series” (1992-95) After designing a Minotaur themed computer puzzle game, Nygma is suddenly fired by a man named Daniel Mockridge. The loss of employment leads to the Riddler’s grand debut. The question-themed rogue lures Mockridge and caped heroes into a real version of the game. Although the heroes and Nygma’s former boss escape the minotaur, they don’t all leave unscathed. Since Riddler escapes scot-free, Mockridge is soon consumed by paranoia. We see the once composed businessman become too scared to walk around his own house without a weapon. While Mockridge lived to make more shady deals, it seems unlikely that he’ll recover from the mental scars the Riddler left.

“Batman: Riddler and the Riddle Factory” (1998) The egotistical Riddler got his 15 minutes of tv fame by crafting a demented quiz show. Contestants who didn’t answer his questions correctly were subjected to a wide range of horrible consequences. However, their torments didn’t compare to the Riddler’s true goal. When the answers to all his questions were put together, they became a single statement that revealed a celebrity’s deepest secret. The fallout from the Riddler’s sudden exposure pushed stars to commit violent acts. In one tragic case, a singer took her life after a deeply personal fact from her past came to light. Seeing the Riddler destroy lives just to get some extra airtime showed how morally bankrupt this villain really is.

“Gotham” (2014-19) There was a time on the Gotham TV series where Jim Gordon and Edward Nygma worked together to solve crimes. But their partnership was shattered by a heinous betrayal. During the second season, Nygma concocts an elaborate scheme to frame Gordon for the death of an officer. The good detective does hard time in prison before his allies allow him to escape. When Gordon asks Nygma to help clear his name, things only get worse. It’s hard to pick what part of the villain’s plot was the most heinous. Over the course of the scheme, Nygma manages to wound Gordon physically and emotionally. But the worst part of this Riddler plot was that he betrayed a friend just to cover up his own misdeeds.

“Batman: The Enemy Within” (2017-18) Riddler presents Batman with yet another sadistic choice in this choose your own adventure narrative. The villain sets up his game by placing three agents in deadly traps and putting Batman and his ally Iman Avesta in a cage. If the Dark Knight answers a Riddler question wrong, an agent will perish. But a correct response forces Batman and Avesta to get hit with painful sonic waves. Riddler twists the knife by making each question a harsh jab at Batman. And since the player chooses what happens, you may see agents die or witness Avesta lose her ability to hear due to the sonic waves. No matter what choices are made, the player will watch Riddler do something truly twisted in this vile game.

#3: Taking His Girlfriend’s Life

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“Gotham” (2014-19) Edward Nygma couldn’t stand to see his love interest Kristen be mistreated by her boyfriend and GCPD employee Tom Dougherty. In a moment of passion, the villain took the officer’s life. Nygma kept his fatal crime to himself while dating Kristen until she became concerned Tom would return. The villain tries to make her feel better by revealing what he did to the officer. But when Kristen takes the news very poorly and tries to get away, Nygma accidentally takes her life. While he didn’t commit this violent act on purpose, he intentionally does whatever he can to cover up her death. We knew Riddle was capable of doing terrible things to his enemies. But we never imagined he’d end someone he loved.

“Batman: Zero Year” (2013-14) It was already bad enough that Riddler wrecked Gotham and made its citizens desperate after flooding the city. But he doubled down on his awful crime by continually messing with the survivors. While the Riddler promised to grant leniency to anyone who could stump him with a riddle, it seems like all the people who questioned him perished. He also monitored nearly every action in the city with drones so that anyone who attempted to leave or defy him would fall. The Riddler kept this cycle of torment going for months before Batman rose up and put an end to it. Unfortunately, the hero couldn’t prevent an untold number of people from suffering or dying at the villain’s hands within the closed up Gotham City.

“Batman: Hush” (2019) Throughout the famous “Batman: Hush” storyline, Bruce Wayne is continually left at the mercy of a mysterious bandaged villain. While the identity of the antagonist and his crimes change depending on the adaptation, Riddler is always the puppetmaster. The comics see the villain fool Batman into thinking the deceased Jason Todd came back to life. In another reality, the question themed villain takes the life of Bruce’s childhood friend and frames the Joker. And every version of the story sees Riddler recruit multiple supervillains and ruin Catwoman and Batman’s relationship. The villain shows absolutely no remorse when all his staggering crimes are revealed. Learning how casual Nygma was about wrecking Batman’s personal life for months proved this villain’s brilliant mind was a seriously dark place.