While he may not be as prolific or prominent as the likes of the Joker or Catwoman, the Riddler has been a persistent member of Batman’s rogues’ gallery since his introduction in Detective Comics #140 in October, 1948, where he established himself as one of the Caped Crusader’s most vexing villains. Whether it’s comics, animation, live action or video games, the King of Conundrums has been a staple of the Batman universe for 70 years.
He’s been portrayed by the likes of Frank Gorshin, Jim Carrey, and Cory Michael Smith. Even Conan O'Brien took a turn at the role, voicing the wrongdoer in 2017’s The Lego Batman Movie.
While The Riddler may sometimes come off as outlandish, cartoonish – sometimes maybe even overly campy - Edward Nygma has frequently proven that appearances can be deceiving and posed a serious threat to the Dark Knight and his allies over the years, becoming a formidable foe over the years.
Let’s look back through his history and check out a few times that the Prince of Puzzles has had Batman’s back against the wall, and how the Caped Crusader inevitably got the upper hand.
Here are the 15 Worst Things The Riddler Has Done To Batman.
15 Invaded his mind and discovered his secret identity - Batman Forever
While it may not be a cinematic highlight for the Dark Knight, 1995’s Batman Forever gave us the only live-action, modern era depiction of the Riddler on the big screen. And while it’s notorious for its campiness and its bat nipples, Jim Carrey’s Edward Nygma actually poses a fairly formidable threat to the Caped Crusaders.
Working as a researcher at Wayne Enterprises, Nygma's latest invention is a device that can beam television directly into its users’ minds. Bruce Wayne rejects the idea, feeling it too dangerous to manipulate people’s brains. The rejection drives Nygma mad. Shortly after, Nygma adopts the persona of the Riddler and begins a criminal campaign targeting Bruce Wayne.
After partnering with Two-Face, the criminal pair devise a plan to learn Batman’s true identity using Nygma’s invention, which they dub The Box.
At a party hosted at Nygmatech, Ed Nygma’s new company, The Box is used to read Bruce Wayne’s mind, learning his greatest fears and uncovering the truth of his crime-fighting alter ego.
Armed with the knowledge of Batman’s secret identity, Riddler and Two-Face storm Wayne Manor, knocking out Alfred, shooting Bruce and kidnapping his love interest Chase Meridian. While Two-Face and his goons are busy upstairs, Riddler prances through the Batcave, using grenades to destroy almost all of the equipment stored there, including the Batmobile.
14 Outsmarted Batman and Robin in a hostage crisis - Batman: the Animated Series
The first episode of Batman: The Animated Series to feature Riddler, “If You’re So Smart, Why Aren’t You Rich,” finds Edward Nygma having been fired from his job as a software designer for the gaming company Competitron.
Two years later, Nygma’s former boss, Daniel Mockridge, is preparing to sell Competitron to Wayne Enterprises when the meeting is interrupted by a riddle posed to Mockridge on the giant stock ticker screen outside the window. Mockridge hurriedly leaves the meeting in a panic.
Riddler eventually captures Mockridge and places him in the Riddle of the Minotaur amusement park, which is based on a game designed by Nygma. The Dynamic Duo are informed that in ten minutes a robotic Minotaur found in one of the park’s mazes will destroy Mockridge unless they get to him first.
Navigating the maze and solving riddles, Batman and Robin eventually find and save Mockridge with less than a minute to spare. Frustrated, Riddler orders the robot to destroy them all anyway, but the three manage to escape.
While the trio survives, Riddler reveals that the entire time he’d been giving instructions, he was doing so from a private plane, having already escaped.
Wayne Enterprises acquires Competitron, but Mockridge is left a paranoid, nervous wreck. He’s added extra locks to his door and sleeps with a shotgun next to his bed, terrified of Riddler’s inevitable return.
13 Gassed a teenaged Bruce - Gotham
The final episode of Gotham’s second season, “Transference”, finds Lucius Fox and a young Bruce Wayne at the whim of Edward Nygma, who has locked them in a room in Indian Hill, a research facility located underneath Arkham Asylum. Nygma has a number of questions for Bruce and Lucius and threatens to release a toxic gas if they fail to answer them correctly. Nygma is interested in whatever information the pair has on who ran Indian Hill. Fox’s answer is Hugo Strange, while Bruce answers Wayne Enterprises, the correct answer.
Nygma isn’t satisfied, asking the follow-up question of who runs Wayne Enterprises. When they are unable to provide the right answer, Riddler releases the gas, laughing maniacally. However, the entire plot was just a ruse perpetrated by the Riddler to find out more about Wayne Enterprises. The gas wasn’t hurtful and only rendered the two unconscious for a short while.
However, after being locked back in his cell by Hugo Strange, Nygma eventually comes to the aid of Lucius and Jim Gordon, helping to unlock a security elevator so the two can access and disarm a bomb that had been planted under the facility by Hugo Strange.
12 Forced Batman to electrocute himself - Batman: Zero Year
Offering a fresh take on Batman’s origin story, Batman: Zero Year features the masked vigilante facing off against Riddler early on in his career. The story starts with Gotham having been destroyed by a massive flood before flashing back to five months earlier. Bruce Wayne has just returned to Gotham, having completed his training to become the Dark Knight.
Shortly into Batman’s crime fighting career, Riddler attacks the city, shutting off the power grid and challenging Batman to figure out how to restore it, promising that he won’t turn the power back on until he is outsmarted. The power is restored momentarily, but Riddler still has the power to flood the city, which he does by blowing up Gotham’s reservoir.
In a final confrontation, Riddler challenges Batman to play a sort of life-sized board game, where he can only move another step closer to Nygma after solving a riddle. Batman eventually gets close enough to capture the Riddler, but learns that, in order to stop an incoming missile strike on Gotham, Batman would need to use his own body as a conduit for thousands of volts of electricity.
Batman attaches himself to an electrode and is able to survive the task, allowing the current to flow through his body, which would have easily destroted an average man.
He restores power to Gotham, saving the day. Having imprisoned Riddler in Arkham Asylum (at least temporarily), Bruce dedicates his life to protecting Gotham as the Batman.
11 Trapped Batman in Virtual Reality - Batman: the Animated Series
One of Batman's closest allies, Commissioner Gordon finds himself in Riddler's grasp in the Batman: The Animated Series episode "What Is Reality?"
The wealthy citizens of Gotham are being targeted by a mysterious hacker who leaves a riddle for each of his victims. Gordon informs Batman that Nygma is deleting all records of his criminal activity from police databases, having his goons infiltrate GCPD and Gotham’s DMV for the hard copies, with the latter incursion nearly ending in Batman’s death.
A package covered in question marks is delivered to GCPD, containing a virtual reality computer terminal that electrocutes Gordon and traps his mind inside. Any attempt to remove Gordon from the terminal will be fatal and Riddler’s software takes such a toll on the commissioner that he’ll soon be dead if Batman doesn’t intervene. The only way to stop Riddler is for Batman himself to enter the VR world.
After a truly surreal trip through Riddler’s VR world, Riddler leaves Batman left with just one minute to solve a puzzle box and save Gordon’s life. Gordon is saved but Riddler suffers a sensory overload and his VR world comes apart.
Batman, Robin, and Gordon track Riddler down in the real world and find his mind is trapped in the virtual world, with Batman commenting, “how to get him out may be a riddle no one can solve.”
10 Made Batman choose between Robin and his love interest - Batman Forever
Early in Batman Forever, Batman is introduced to Dr. Chase Meridian, a psychiatrist specializing in multiple personalities that was asked to consult on the Two-Face case. She quickly becomes enamored with Batman.
Once Riddler starts leaving puzzles for Bruce Wayne, he consults with Dr. Meridian (as Wayne) and eventually invites her on a date to Gotham’s Charity Circus, after which a fledgling romance between the two is born.
Bruce eventually goes as Batman to Chase’s apartment, where she tells him that she’s in love with another man, choosing Bruce Wayne over Batman. Bruce tells Dick Grayson that he has finally found peace with Chase and will retire as Batman, finally content.
Bruce tells Chase he was the Batman, but the peace doesn’t last long. After Riddler and Two-Face attack Wayne Manor, they leave Bruce incapacitated and kidnap Chase.
Batman and Robin head to Riddler’s lair to rescue her, but Dick is captured, and Riddler forces Batman to make a sadistic choice. Dick and Chase are being held in cages that will plunge one of them into the water below.
Riddler forces Batman to choose who he’ll save: his recently orphaned ward or the woman he loves.
Since he’s Batman, our hero is able to save both of them, destroying Riddler’s brainwave device in the process and causing him to have a mental breakdown.
9 Humiliated Batman in front of Gotham's elite - Batman: The Animated Series
In a third season episode of Batman: The Animated Series, after being released from Arkham Asylum, Nygma licenses his Riddler persona and his puzzle technology to a Wacko Toys, a Gotham-based toy company. He seems to finally be on the straight and narrow, but Batman and Robin suspect he’s still up to his old tricks.
When Batman sees a commercial for Riddler’s line of toys featuring a cryptic number, he’s suspicious it refers to map coordinates for the First National Bank and stakes it out to prevent Riddler from robbing it. When Batman realizes flipping the numbers over gives him a different address, he and the Boy Wonder head over and find Riddler’s thugs robbing a jewelry store. A fight ensues and a large display case topples over onto Robin. As Batman helps to free him, Riddler’s thugs are able to make their escape.
After foiling their plot, Batman goes to confront Riddler at a high-class party the criminal is attending with Gotham’s elite.
Batman doesn’t have hard evidence, though, and Riddler uses the opportunity to broadcast their conversation to all of the partygoers, humiliating him.
The partygoers laugh at Batman’s expense, leaving the Dark Knight looking incapable in front of the best of Gotham.
8 Attached a bomb collar to Catwoman's neck - Batman: Arkham Knight
One of the more significant and time consuming side mission quests in the 2015 Xbox One/PS4 video game Batman: Arkham Knight is to help save Selina Kyle from the Riddler’s grasp.
Nygma has kidnapped Catwoman, one of the few people Batman personally cares about, and is using her as a pawn in a sadistic game meant to break the Dark Knight.
Riddler has strapped a bomb collar to Catwoman’s neck, and the only way to remove it is for Batman to help her retrieve several keys for the collar’s locks. To unlock the keys, Riddler has placed numerous challenges, races and puzzles around Gotham that Batman must solve to retrieve the right keys.
If Batman fails in a quest or instructs Selina to use the wrong key, the bomb will detonate off screen, destroying Catwoman in the process.
In addition to the puzzles, Riddler has also hidden more than 240 Riddler Trophies throughout the city, so even after you’re done saving Catwoman, there are still plenty more Riddler games to play.
Once all the keys have been obtained and all of Riddler’s trophies have been found, Nygma himself makes an appearance, wearing a giant mech suit. With Catwoman at Batman’s side, they fight together to take Riddler down once and for all.
7 Destroyed Wayne Tower and Lucius Fox - Batman: The Enemy Within
Appearing as one of the main villains in the second season of Telltale Games’ Batman: The Enemy Within, Riddler is shown early in his criminal career, depicted as one of Gotham’s earliest supervillains. During a confrontation with Batman, Riddler leaves the vigilante with a puzzle box before making his escape.
The box turns out to contain a radio signal emitter that would be used to target a homing missile to the box’s location. Batman brings it back to the Batcave, but since the cave has a frequency scrambler, it fails to draw the missile strike. Wanting to know more about the box, Batman brings it to Wayne Enterprises to have it further analyzed.
However, with the Batcave’s scrambler no longer thwarting the signal emitter, the box is able to make a connection with the missiles.
An airstrike ensues, which partially destroys Wayne Tower and ends Wayne Enterprises Chief Technology Officer Lucius Fox, Wayne’s longtime ally.
In his final moments, Fox insists Wayne save himself and Fox’s daughter Tiffany. Fourteen other Wayne Enterprises employees were injured in the attack, but Lucius was the only one who lost his life.
Following the attack, at Fox’s funeral, Bruce Wayne vows that he will find the Riddler and bring him to justice.
6 Choose between Life or Deaf - Batman: The Enemy Within
Later in the Telltale series, Riddler kidnaps four government agents and hold them captive. Three of them are placed in one trap, while the fourth, Agent Avesta, is placed in a separate one. After having figured out the Riddler’s location, Batman attempts to save the hostages, but eventually finds himself locked in the same trap as Avesta.
The Riddler poses an impossible choice to the Caped Crusader.
If he solves three riddles, the other agents will be set free. However, solving them would mean he and Avesta would be blasted with sonic cannons capable of destroying them both.
Since this is a point and click adventure game, there are numerous potential outcomes. If Batman refuses to answer the riddles, Riddler will begin taking out the agents in the second cage. However, if Batman decides to play along with the Riddler’s games, he and Avesta are blasted by the sonic cannons. Both characters ultimately survive the ordeal, but Avesta is left permanently deafened because of Batman’s decision.
In either case, Batman eventually uses a drone provided by Tiffany Fox to help him escape his cage and take down the Riddler.
5 Revealed Batman was created by a demon - Dark Knight, Dark City
One of the more sinister depictions of Riddler, Batman: Dark Knight, Dark City opens in 1765 with a group of occultists trying to summon the demon Barbathos. Before the ritual is complete, though, the group is attacked by what seems to be a giant winged monster and flee in terror.
One of the occultists writes a confession years later, which is eventually found by the Riddler in modern times as he’s stealing antique collectables. He decides to try to raise Barbathos himself and decides to use Batman as the human sacrifice needed to complete the ritual.
Riddler steals four lives and uses them as bait to get Batman to complete the tasks needed to recreate the ritual. After surviving Riddler’s trials, Batman manages to save all the babies and tracks Riddler to the temple where the original ritual was held.
After capturing Batman, Riddler is preparing to make the sacrifice when Barbathos speaks, terrifying Riddler, who runs from the temple, seals the tomb and sets it on fire.
Barbathos explains that, instead of a demon, he is the literal spirit of Gotham City and created Batman as a means to one day set him free.
After being saved by Alfred, Batman decides that, even if he was created by a demon, it was his life experiences that shaped him into the man he is and vows to continue protecting Gotham.
4 Stole Batman's Soul
The Primal Riddle opens with the Caped Crusader already in the middle of a battle with Riddler atop a Gotham clock tower. Riddler kicks Batman off the roof onto the power grid below where he is almost electrocuted to death and has an out of body experience before being resuscitated.
Batman is saved but he’s acting strangely, barely speaking and seeming detached. The Riddler notices this change and puzzles out that when Batman had temporarily went to the other side, his soul left his body and never came back after he was saved.
Batman’s spirit is inhabiting a fireman and Riddler tracks him down and transfers it into his own body.
But he can’t control Batman’s will and instead transfers the soul into an accomplice, Chère, before having her locked in a dumpster, hoping the spirit will wither without its real body.
A soulless Batman tracks Riddler to his old apartment where he falls into a trap Riddler had set up for him. Locked in a water filled room with electrified walls, Batman will be fried to a crisp if he or the water touches the charged walls. After using a secret toolkit to escape the trap, Batman eventually pursues Riddler to the construction site where Chèrée is being held. He is attacked a final time by Riddler but manages to fight him off.
Chère passes in Batman’s arms as his soul returns to his body. The GCPD arrives to arrest the Riddler and he begins crying as he carries Chère’s husk away from the scene.
3 Made Batman's childhood friend into his worst enemy
Batman’s childhood friend, brain surgeon Thomas Elliot, is summoned by Alfred for help after Bruce fractures his skull in a chase with Catwoman. After being nursed back to health, Bruce attends an opera accompanied by Thomas, but it is interrupted when Harley Quinn and Joker attack the opera house, with Joker seeming to take out Thomas in the process.
At Thomas’ funeral, Bruce tells Dick Grason that he suspects a criminal mastermind is pulling the strings and making Batman’s villains behave seemingly out of character.
Batman is consulting with longtime friend and ally Harold Allnut when Harold is shot down by a man whose face is wrapped in bandages and goes by the name Hush. It’s revealed Hush is actually Thomas Elliot, with it being implied the man shot at the opera was Clayface in disguise. Elliot has held a grudge against the Wayne family for decades, but he is shot and apparently taken out by Harvey Dent before he can exact his revenge.
In the epilogue, it is revealed that Riddler had been behind the plot all along, having deduced Batman’s identity through a Lazarus Pit and aligning himself with Elliot.
Batman confronts the Riddler, knocking him unconscious. He’s unconcerned with Riddler knowing his identity, since if it was revealed, Ra's al Ghul would know Riddler had used the Pit and would send the League of Assassins after him.
2 Bombed Batman - Batman: The Animated Series
After Riddler makes him a laughingstock to Gotham’s most rich and powerful denizens, Batman vows that he’ll return to put Riddler away for good. Riddler admits to one of his goons that Batman “is going to catch me, sooner or later,” saying Batman is his only worthy opponent.
In a new commercial for Wacko Toys, Riddler gives a clue to Batman regarding the Gotham Convention Center. Batman arrives solo, with Robin still recovering from the previous incident at the jewelry store. Batman encounters a giant puzzle box that almost crushes him, which contains a video message from the Riddler.
The convention center has been rigged with an enormous bomb and Batman has just ten seconds to escape.
The bomb detonates and Batman only survives by taking shelter inside a nearby safe.
Using his own technology against him, Batman had used the same two-way radio that Riddler used to embarrass him at the party to broadcast a confession from Nygma to commissioner Gordon.
Nygma is again arrested, having violated his parole, and is taken back to Arkham. As he’s taken away, Riddler pleas with Batman to tell him how he survived the blast. The episode ends with Riddler back at Arkham, shouting that it’s impossible for Batman to have outsmarted him.
1 Discredited Batman
After spending the better part of a year in a coma, Riddler appears at Wayne manor, claiming to have been reformed and rid of any criminal tendencies. Riddler has gone into business for himself – this time a legal business – as a private investigator. Someone is trying to frame Bruce Wayne for murder, but Riddler is there to exonerate him.
Batman sets out to find who’s behind the setup and quickly runs out of clues. It’s then that he returns to the Batmobile to find Riddler sitting on the hood, mocking and condescending Batman for having hit a roadblock. The two form a sort of uneasy truce as they work together to solve the case, with Batman still being suspicious of Riddler the entire time.
They eventually solve the case and Riddler is given all the credit for doing so, making Batman seem like an ineffectual detective to Gotham’s citizenry.
Batman had found another clue during their investigation and deduces the real criminal to be Sarah Morton, the woman who originally hired Riddler to investigate. He tracks her down and turns her into Commissioner Gordon.
The story ends with Riddler sitting in his new office, puzzled as to how Gordon possibly could have put the pieces together better than he had, before ultimately realizing that it had been the work of Batman all along.
Did we miss any awful thing that the Riddler has done to Batman? Let us know in the comments!