According to Alfred Pennyworth, Riddler began his criminal career in Gotham, during the years it was controlled by Thomas Wayne, Carmine Falcone, and Mayor Hamilton Hill. He would terrorize the city for some time, which lead to the trio giving him his own berth to operate out of. However, during the midst of his criminal career, he disappeared so suddenly that many people believed he had died.
In reality, Riddler had been approached by the Agency, a government organization with multiple complaints about unethical operations, to join them, having seen his potential in their scientific division, SANCTUS. During his time there he did research for many of their top secret projects, including Project LOTUS, an experimental virus with regenerative capabilities. After multiple failed tests, Riddler was infected with the virus in an accident and was expected to die. Instead, he survived, though his brain's chemistry was severely damaged, causing the emergence of both his Obsessive Compulsive Disorder and Narcissism. Riddler was kept within the confines of SANCTUS for years and was constantly monitored, their scientists hoping to study the effects of Project LOTUS. Eventually, he would be able to escape the organization and installed a backdoor into their network, ensuring he could access the files he needed to expose the Agency and get his revenge on the organization.
Riddler became an international criminal, committing crimes throughout different countries and building up a small criminal organization of his own. Though his goal was to obtain his revenge on the Agency and SANCTUS, he also planned to regain his place in Gotham City as its most notorious criminal. Riddler eventually made his presence known when he broke the inmates out of Peña Duro Penitentiary on Santa Prisca, murdering the warden in the process. It was during this attack that he met the criminal Bane, who would become both a close ally and friend. Having heard tales of Bane, Riddler believed that the mastermind could be a perfect candidate for his growing numbers.
After this, he gained the attention of the Agency and its current director Amanda Waller. Later he was almost captured by them while in Sudan, but managed to escape. At some point, he became acquainted with Selina Kyle/Catwoman, after hiring her to steal a painting from the Louvre. He would often work or hire the cat burglar/mercenary afterwards, becoming a frequent contact for her.
Eventually, Riddler founded the Pact, a group of criminals assembled throughout the globe by the villain over the years and supplemented by Bane's fanatical followers the brute assembled when he was in Peña Duro. When Riddler returned to Gotham, he completed his recruitment with new criminals Victor Fries/Mr. Freeze, Harleen Quinzel/Harley Quinn, and former Arkham patient "John Doe". Riddler christened himself as the leader of the group and, after putting their various gangs and resources together, planned an attack on SANCTUS to obtain both LOTUS and his long-lusted revenge on the organization.
In return for their assistance, the other members would receive LOTUS to cure the various ailments they were suffering from or wished to cure. The only exception was John Doe, who had no urge or need to use the virus on himself and was simply drawn to the Pact due the chaos they would unleash in Gotham City. However, Riddler also intentionally kept LOTUS's side effects secret from the Pact, knowing that this knowledge might compel the other members to not agree with his plans. He also approached Catwoman to join them, as he also had need of her unique burglary skills to secure specific equipment necessary to the group's plans, but she declined.
After learning of Batman and his reputation amongst both Gotham citizens and criminals, Riddler, against the wishes of his fellow members, decided to attract the Dark Knight's attention, hoping to eventually kill him and make his return known to the authorities and civilians in a spectacular fashion. For his, he decided to attract Waller's attention and draw a number of the Agency's operatives to Gotham, targeting and killing the ones they sent.
For his plan, Riddler created a long ranged signal and made a deal with arms dealer Rumi Mori to receive radio-wave guided homing missiles. With the necessary components collected, Riddler planned to hack the agents' phones, make them produce the guidance signal and, after allowing it to play long enough, fire a radio-wave guided missile to their locations. After Mori bowed out, Riddler set up plans to murder the arms dealer in retribution. He also began completing recruitment for his criminal organization, specifically targeting the more intelligent criminals he could find. One such was Eli Knable, who became his second-in-command.
In the weeks coming up to the Pact's attacks, Riddler and his men confronted Mori within his own casino, the Virago. When a security guard tried to escort him out, he murdered him and locked down the building. After taking hostages, the Riddler then place Mori in one of his death traps and promised to let him out, if he successfully solved a riddle. During the commotion, Batman appeared and incapacitated a number of his men, including Knable. As Riddler held Batman at knifepoint with his cane, the vigilante ordered Commissioner Gordon to raid the casino.
Stunned at this turn of events, Riddler fought with Batman, but was easily overpowered by the vigilante. Deciding to make his escape, he activated the death trap to murder Mori, hoping it would distract Batman long enough for him to leave. However, the vigilante was able to disable the trap and confronted Riddler on top of the Virago's statue. Stunned on why he had saved Mori from certain death, Riddler was once again defeated by Batman. After detonating a bomb to open his escape route, Riddler then left Batman a puzzle box. Threatening to kill others unless he was able to solve the puzzle, Riddler destroyed the statue's supports and made his escape.
Batman would be able to solve Riddler's box, but only found a signal emitter inside. Due to the Batcave having a scrambler installed, the missile was unable to fire and locate the Batcave. After taking it to Wayne Enterprises to look at it closely, the signal was allowed to play long enough to send a detonation order, resulting in the minor destruction of Wayne Tower and the death of Lucius Fox.
During the next week, Riddler purchased an abandoned Water Tower in the East End of Gotham and created another death trap within it. He also set up a supercomputer capable of breaching SANCTUS's security and another trap to guard it from both the Agency and other members of the Pact. After kidnapping Special Agent Mario Fernandez, he took him to the trap he had set up and forced him to solve it, promising a hint to what he was planning for the Agency. Fernandez was unsuccessful and was killed by the ultra-sonic emitter.
Batman and Gordon would later discover the trap, thanks to a tip the vigilante had received from one of his contacts. Using evidence they were able to find, pointing to Fernandez's mistakes, Batman and Gordon were able to solve the puzzle, finding one of the homing missiles bought by Riddler. The criminal then appeared on screen, revealing his past with the Agency and tried to explain their responsibility for his condition. During this, Riddler also mocked Batman for not telling Gordon about his connection to the rocket being fired at Wayne Enterprises, knowing he had a connection to Lucius Fox.
Later that night, Riddler retreated to his personal barge, the Lady of Dublin, along with his men. He was also able to locate and kidnap four of the Agency's agents, including Iman Avesta and Vernon Blake, placing them within death traps. As he and his men prepared to murder the agents around Gotham, Batman arrived, having retrieved a location from either a deal with Mori or interrogating Knable. As he defeated Riddler's goons, he made an attempt to knock out the criminal with his Bat-Stunner. However, the criminal had prepared for this, as he was wearing protective materials under his suit. As Batman released Avesta from her trap, Riddler activated a trap to hold Batman. He then revealed himself to be conscious and showed the vigilante where the missile launcher had been hidden.
With the vigilante now in his grasp, Riddler threatened to murder the other hostages, unless Batman solved three simple riddles. However, in solving these, he and Avesta would be blasted by the sonic devices he had set up in their cage, which could kill her within those three blasts. Depending on Batman's decisions, two possibilities will happen.
If Batman refuses to answer one of or both of the riddles, Riddler will murder Blake. If the first riddle isn't answered, he will also kill another agent if Batman doesn't answer the second correctly. During the final riddle, Batman uses a drone to emit the signal, directing one of the missiles towards the cage. Furious at these turn of events, Riddler fires the rest of the missiles to kill the other agents, but these are directed into Gotham's river by the drone, where they can detonate without harming anyone. Batman then defeats the criminal and places him in bonds. However, Riddler considers it a victory, having made Batman kill the agent(s), even if it was indirectly, and broken his code.
If Batman complies with the Riddler's game, Riddler subjects him and Avesta to the blasts. However, during the final riddle, Batman instead uses a drone to emit the signal, directing one of the missiles towards the cage. Furious at the turn of events, Riddler fires the rest of the missiles to kill the other agents, but these are directed by the drone into Gotham's river, where they can detonate without harming anyone. Batman then defeats the criminal and places him in bonds. Though he admits defeat, Riddler mocks the vigilante for having harmed Avesta and rendered her deaf to save the other hostages, commenting that his "friends" would have been proud.
Riddler revealed that he had set the plan up to draw [the Pact's] attention and show them how he impressive he believed he was. Realizing that one of their former comrades may have set him up, he was shot by a poisoned dart from a drone, operated by Lucius Fox's daughter Tiffany. As he died, Riddler mentioned how they had "broken the Pact", causing Batman to wrongly believe that "John Doe" and "his friends" had been involved in his attacks.
The Agency would place the blame on the GCPD for Riddler's death and later take his corpse into possession. Batman would also take his cane, which he kept in the Batcave to remember his victory over the criminal. Hoping to extract samples to replicate a usable version of LOTUS, they placed it into a cryogenic unit to preserve it and transfer the corpse out of the city. After learning Riddler's death, the Pact put together a plan to retrieve his corpse, so that they could access the secret location of SANCTUS's lab and Project LOTUS. After they retrieved a Phalanx Key and EMP generator from Wayne Enterprises, they attacked the convoy set to escort him and collected his body.
With assistance from Catwoman, they would duplicate his eyes to fool the retinal scanner and access the files. After learning about SANCTUS, she would attempt to stop them in retribution for his death and Lucius Fox's, ultimately leading to her working with Batman. The Pact would also keep Riddler's body, so they could retrieve bloods samples to synthesize non-lethal versions of Project LOTUS and cure their various ailments.
Unfortunately, during their attack on SANCTUS's labs, the Agency would steal the samples and drain the blood from Riddler's body, leaving the case damaged. With this, his corpse would decompose at an accelerated rate, ensuring the Pact couldn't get any more samples. The remaining samples were later destroyed by Avesta to ensure the Agency couldn't use them as bargaining chips for the Pact's cooperation.
Riddler's murder would remain unsolved for weeks, leading the Agency to blame "John Doe", now the vigilante/criminal Joker. However, he was not responsible and, depending on whether he becomes vigilante or criminal, either would wrongfully blame Waller or deduced that it was actually Tiffany Fox. Batman would eventually discover the truth when she either confessed to save Waller's life or was forced to reveal it to him during Joker's game. Depending on whether she learns Batman's identity, Tiffany would either see her actions as justified or regret doing so. If Batman confronts the villainous Joker, she can be taken into custody by the Agency to await trial for Riddler's murder.
Despite his high intelligence, the Riddler was brash and arrogant, taking pleasure in beating his opponents and believing himself to be superior to his victims and pursuers. Riddler also seemed to be sadistic, taking pleasure in seeing his victims either scared or be gruesomely injured. Riddler would also leave elaborate clues and puzzles behind at his crimes, believing that the people who would not be able to solve them, something which he was proven wrong on many occasions. He was also willing to kill civilians or put them at risk, as seen when he ordered one of his men to execute a hostage to distract Batman.
Riddler's costume consisted of a dark green suit jacket, a purple shirt, a green tie, dark green trousers and a pair of black leather shoes. To hide his identity, he would also wear a green domino mask and a hood, the latter of which seems to been sown to his suit jacket. Riddler also wore a golden question mark on his left lapel and black gloves, to prevent him from leaving evidence that could lead to the authorities learning his identity. It is unclear how much protection he wore, but it is known that he had equipped a device that neutralized Batman's Bat-Stunners during their final confrontation.
Riddler would wield a golden-topped black cane during his crimes, which he used as both a weapon and a tool during his crimes. The top of this cane was stylized as a question mark, though the inside of it was sharp enough to cut human flesh. Riddler would use this as a method of execution of his victims and within combat with his opponents, using the hooked edge to grab at his enemies and objects to use in combat. The hook could also act as a grappling hook, with a button to detach and fire it at specific objects. This also came with a pulley system to pull the Riddler towards his target. The cane also had a multitude of different buttons on it, which could act as transmitters to activate or operate devices and contraptions, such as explosives and his death traps.
Riddler would often leave these boxes at his crimes, believing that his pursuers would not be able to solve them. These would often consist of elaborate puzzles, including riddles and methods to reshape them, and clues to his plans. Riddler would also place advanced circuitry within them for the purpose of challenging his opponents, such as one where the person had to manipulate waveforms to access their next clue.
Riddler would use death traps (or "murder boxes", as other people called them) to either taught his victims or challenge his opponents. These would consist of many different machines or devices, including controllable saw blades, sonic blasters and a multitude of different devices, most of which he made himself. One such was used on Rumi Mori, where he was trapped within a small glass chamber and his fingers were removed for each time he got the solution to a riddle wrong. Another trap, set for Batman, forced the vigilante to solve a puzzle whilst coping with a sonic blast if he got a riddle right, or killing an Agency agent if he refused or got it wrong.
To Riddler, Batman was a "wannabe" who filled the void he himself had left after taking a leave from Gotham. Upon coming to blows with Batman, Riddler admitted to his formidable skill and forfeited the fight by causing a diversion and leaving a puzzle. After Batman and Gordon solved Riddler's "murder box", Riddler started to admire the vigilante's intelligence and began to see him as a worthy opponent. However, he never shied away from mocking the vigilante, particularly with Lucius' death, and would try to use his own moral code against him in their final encounter.
It is mentioned several times that Riddler considered the Pact his friends, despite adversity he had with several members. It seems that he was the closest to Bane, who considered him to be his friend and would seek retribution on his murderer. It seems he and Harley Quinn had a purely professional relationship, though he was unwilling to listen to her advice regarding the group's secrecy. It also seems that Riddler had a very poor relationship with Joker, the two being constantly arguing and Joker considering him to be a "rude know-it-all". It's currently unknown how he and Freeze felt about each other, but likely to have been purely professional.
Mori had sold radio wave guided homing missile and silos to Riddler prior to their confrontation at Mori's casino. After Mori backed out of their deal for either realizing Riddler's plans or after he requested the use of his biotech company, Riddler swore retribution on Mori and attacking him at the Virago casino. The encounter resulted in two of Mori's fingers being cut off, leaving him traumatized by the experience, and being placed under surveillance by the Agency. If given the chance and incentive, Mori would be easy to sell out Riddler.
Eli was Riddler's right hand man and one of his most trusted henchmen. Having worked for him for some time, Eli eventually grew fearful of the criminal due to his brutal methods, sophisticated machines, and methods of torture. Even whilst captured, he refused to speak, despite the brutality of the Agency, due to his fear that the Riddler would take retribution. Eli was also fearful that Riddler's plan could not be stopped, believing the criminal to be smarter than even Batman.
- "Stop me if you've heard this one before. I begin and have no end, and I end all that begins. Who am I?"
- "Our issues can't be solved with handshakes, Mori."
- "I've heard stories in the street about you, Batman. You're the biggest name in Gotham since... well, since I've left town."
- "You're supposedly the 'world's greatest detective', yet here you are, completely at my mercy. I don't see much evidence of that. I expected more of a battle from you, Batman. Something longer, more of a match of wits. While my men mop up what passes for law enforcement in this town. It would've been hard to deal with you both at the same time, but no cause to hold back now. You surprised me a little with how quickly you arrived, but just a little."
- "Let me show you how it was done, back in the day."
- "You should see your face. Its confusion is delightful. I think I'll take it with me."
- "Halfway there, Batman. Means you've got half a chance of stopping a whole lot of pain. To be honest, you're already doing better that I thought. But don't sit around feeling pleased with yourself. Unless you want to see me tear this city apart."
- "Don't say stupid things, okay? Not when you've just started earning my respect."
- "I wasn't always like 'this'. The Agency made me."
- "That's the thing about having a mind like mine. You remember everything... even the things you'd rather not."
- "Come on, now. Don't get your tights in a twist. I knew you weren't sharp enough to do it on purpose. There's no room at the top for schoolboys who're too squeamish to fight in the gutter. You don't have what it takes to be a player in this town. Not without giving up those 'values' you hold so dear. Game on!"
- "You brought this on yourselves, all of you."
- "You can't possibly think clunking a few heads is enough to make me roll over."
- "Now, let's get started. We have a lot to get through. I'm curious to see how you'll handle it all."
- "Very good Batman, you saved a life. But..."
- "Well, congratulations Batman. You managed, even in my twisted game, to keep everyone alive. But at what cost?"
- "Welcome to the maelstrom. Deeper and deeper you go. This is the vortex of life, pulling you down into its depths."
- (After stepping on a panel) "Ah ah ah! To truly understand my mind, you must first walk a mile in my... well, certainly you know the rest."
- "I take you by night, by day I take you back. None suffer to have me, but do so from my lack."
- "This is my city. This is my plan. Nobody will interfere!"
- This iteration of the Riddler differentiates from other versions, as he is skilled at hand to hand combat, older than Batman (mentioned to be sixty by Amanda Waller) and wears a hood rather than the traditional bowler/derby hat. He is also treated as a very serious threat (rather than comedy relief), as he is recognized as one of Gotham's first "supervillains".
- The version of Riddler seen in Gotham is the only other version of Riddler thus far who is older than Bruce Wayne, and much like this Riddler, predates Batman.
- Whilst it is confirmed that the Riddler's forename is "Eddie", possibly short for Edward, Edgar or Edwin, his surname is currently unknown. Although, it is possible that it's either Nigma or Nashton.
- Despite being a minor antagonist, Riddler serves as the main antagonist in The Enigma.
- Agent Avesta has mentioned that Riddler does show signs of Obsessive Compulsive Disorder (OCD). This is also divulged by seeing the way he arranges the items on his desk, bed and pantry in his hideout.
- It is possible that Riddler was the client who hired Catwoman to steal the prototype Phalanx Key from Wayne Enterprises. It can be assumed that he needed it bypass SANCTUS' electronic locks and get revenge on the organization. However, with a backdoor already installed within their systems, he simply could have found a way to bypass them himself.