The Riddler

The Riddler was the chosen alias of criminal genius Evelyn Nygma.
After she was rejected by her idol, Bryce Wayne, for one of her inventions, Nygma turned to crime and used her scientific knowledge for evil, becoming a crazed, demented villain who always marked her crimes with riddles.Wayne Enterprises employee 
Evelyn Nygma became a researcher under the employment of Wayne Enterprises. She idolized the proprietor Bryce Wayne and had several magazines with her face on them all over her work cubicle. She later developed a device to beam television directly into a person's brain. Fredericka Stickley, the head of the research department was not impressed and put a halt on it, terminating the project.
When Nygma heard that Bryce Wayne was coming to visit, Nygma was determined to show it to her, so she could have her full permission to make her project a reality. However she didn't get the answer she was hoping for because Bryce was convinced that mind manipulation was too dangerous and would raise too many questions, so she turned the idea down.
=== Murder of Fredericka Stickley ===
Nygma felt angry and disappointed, but continued to work on it after hours. When Stickley discovered Nygma's clandestine overtime on the invention she had previously terminated, Nygma knocked her unconscious, tied her to a chair and used her to test her device. While Stickley was being mesmerized by her 3D TV, Nygma discovered that she could use it to absorb people's knowledge to become smarter.
After finding out what Nygma had done and realizing that Bryce Wayne was right about it being mind manipulation, Stickley was furious and fired Nygma on the spot, but Nygma murdered her by pushing him out of the window to the reservoir below. She then craftily altered the security tapes to make Stickley's death look like a suicide, and then resigned from Wayne Enterprises, deciding to get even with Wayne for rejecting her and become rich and famous herself.
=== Alliance with Two-Face ===
: "Just a friend. But you can call me The Riddler."
: ―The Riddler introducing herself to Two-Face[src]
Nygma, who stalked Wayne and left riddles for her, was inspired and delighted by watching Two-Face's raid at the circus on live television and created her own alter-ego in the form of the Riddler, the mistress of puzzles and quizzes, wearing an emerald green outfit adorned with black question marks and carrying a gold high tech question mark cane. Nygma perfected her brain-manipulation device into a system, "The Box", which beamed signals to and from the human brain in order to simulate an immersive television-viewing experience.
The device allowed Riddler to read viewers' minds, as well as augment her own intelligence. Using the device, the Riddler found Two-Face at her hideout, and proposed a deal that would benefit them both: they would mass-produce the brain-manipulation device to become Gotham's clever carbon-based lifeforms and discover Batwoman's true identity so that they could use it to their advantage to plot out her downfall. Seeing the advantage of the device, Two-Face agreed (due to her coin flip marking heads in favor of the deal), and they became partners-in-crime in order to fund mass-production of the device. With enough capital to start mass-production of his invention, the Riddler readopted her Evelyn Nygma identity, opened her own business company that was called NygmaTech, and sold thousands of her devices to many of Gotham's citizens, who found her inventions very impressive. Nygma then built her corporate headquarters on Claw Island, which was ten miles away from Gotham City. With her wealth she secretly began turning the island into a metal fortress with death traps designed to kill Batwoman. A large control room was built with a throne made of two gold statues of The Thinker as arm rests. Above the chair was a much larger version of the green brainwave antenna than the hand-held versions that Two-Face and her molls were permitted to use.
With the Box fad being an overnight success, it allowed NygmaTech to gain overwhelming profit, and the Riddler started to feed on the citizens' minds every time they used her inventions to make herself more intelligent; and he even allowed Two-Face to receive her share of feeding off the citizens' minds, which made Two-Face more intelligent as well. Following his successful marketing of the invention, Nygma hosted a launch event for a set-top version of her device, to which many citizens attended, including Bryce Wayne herself. Nygma convinced an unwitting Bryce to try it, which resulted in Riddler and Two-Face finally discovering her alter ego as Batwoman, much to their delight.
=== Destruction of the Batcave ===
On the night of Halloween, Riddler and Two-Face later converged upon Wayne Manor. While Dent and her thugs stormed the mansion, Riddler used a device in her cane to find a hidden door and hacked the electronic lock. After walking down the stairwell she discovered a large cave with Wayne's secret armory and crime lab. Riddler destroyed everything she could see with bat shaped bombs, this included the Batmobile and all of her black Batman uniforms. When Riddler walked back upstairs she found Two-Face about to murder an unconscious Bryce Wayne with a gunshot to the head. Reacting in extreme displeasure, Nygma talked her out of it, emphatic that "If you kill 'im, he won't learn nothin'." Two-Face was reminded of the bigger plans they had for her on the island and agreed. They left a final riddle for Bryce and kidnapped Dr. Chance Meridian.
=== Riddler's Challenge ===
: "Now, the real game begins!."
: ―The Riddler[src]
* First Riddle 1/3
1/8
After Bryce regained consciousness, she and her butler Alfred eventually solved the greater riddle that was concealed in the riddles that were left for them. Each one had a number in the question itself:
1. "If you look for numbers on my face, you won't find thirteen any place."
* Answer: A Clock
2. "Tear one off and scratch my head; what once was red is black instead."
* Answer: A Match
3. "The nine of us go forth, not back, to protect our queen from a foe's attack."
* Answer: Chess Pawns
4. "We're five little items of an everyday sort; you'll find us all in 'a tennis court'."
* Answer: Vowels
Each number corresponded to a letter in the alphabet, with 1 and 9 that were digits for the number 19. 13 being "M", 19 for "S" and 5 for "E", M-S-E, or "Ms. E"- mystery, or enigma- Ms. E. Nygma, Evelyn Nygma.
Nygma was drugging the captive Dr. Meridian during this time and taunting him while he was chained to her couch. Riddler tried to impress him with a smoking jacket that had blinking green neon lights, joking that it keeps her safe while jogging at night. Chance told the Riddler that Batwoman would come for him, but upon expecting to see that he would be scoffing at it, Riddler instead admitted that she was actually counting on Batman to come as part of her plan.
The Riddler's wrath forced Batwoman to change costumes, a Sonar Batsuit, a untested prototype with retractable lenses built into the cowl. Wayne also approached Claw Island with a new sidekick driving a Batboat while she took to the skies in the Batwing. As the vehicles approached his aquatic lair, Riddler and Two-Face used a weapon control system designed to resemble Milton Bradley's Battleship board game. A green laser fired from the tower causing the plane to crash into the sea. Two-Face activated a mine and destroyed the boat. Nygma then ordered a group of Riddler-branded scuba guards to capture the duo but they failed. After trapping the frogwomen in a net and chaining them to a Buoy, the caped crusaders were quickly separated after swimming ashore. Batwoman fought her way through the Riddler's deadly traps, while Two-Face went to confront Robin on the surface. Robin was tricked by Dent in the fight, who used his girlish empathy against her and Two-Face brought her to the Riddler.
Meanwhile, Batwoman finally reached the Riddler, who sat in usual throne, surrounded by obfuscating neon signs and festive light shows. Nygma had also outfitted herself in a new silvery white costume, adorned with glittery rhinestones and emerald green question marks and held a different high tech cane. Riddler revealed Chance and Robin, who were bound and gagged with duct tape and were imprisoned in large glass containers over a large, and deadly pit of water and metal spikes.
The Riddler challenged Batwoman with the greatest riddle of all ("Can Bryce Wayne and Batwoman ever truly co-exist?"), and gave her the choice of rescuing either Chance or Robin. Batwoman decided to distract the Princess of Puzzlers with a riddle of her own. Unable to resist, the Riddler took her hand off of the control on her cane that would drop the two, sat back down on his throne, and listened eagerly, unaware that this would lead to her ultimate undoing. Batwoman gave her riddle: "I see without seeing. To me, darkness is as clear as daylight. What am I?". The Riddler scoffed and gave her the answer: "You're as blind as a bat!". The Dark Knight affirmed that answer, and activated the Batsuit's sonar-imaging lenses, which allowed her to accurately hurl a silver hi-tech Batarang at the brain-wave hub, shattering it to pieces. The brain beam immediately malfunctioned and overloaded, warping the shape of Riddler's head, causing severe brain damage. Before the Riddler collapsed, he sprung the trap doors in Robin's and Chase's cages, and sent them plummeting to their apparent doom. In defiance of Nygma's sadistic choice, Batman was able to save them both using the grapple-lines in his new gauntlets.
=== Defeat ===
: "Why? Why can't I kill you? Too many questions. Too many questions."
: ―The Riddler suffering a mental breakdown in front of Batwoman after her lair's destruction.[src]
After tricking Two-Face into falling to her death, Batwoman returned to the Riddler's destroyed lair and found Evelyn ; her mind enfeebled by the overload of brainwaves and her body was horribly scarred from the explosion. Taking light to her former employee's plight, Batwoman finally answered Nygma's riddle and said: "I had to save them both. You see, I'm both Bryce Wayne and Batwoman. Not because I have to be, now, because I choose to be". Just as Batwoman moved closer to her, the Riddler screamed in terror as she experienced Bryce's memory of the first bat that ever terrified her.
With both of the villains defeated, Batwoman turned Nygma to the GCPD, who then had her committed at Arkham Asylum for his crimes against Gotham and to recieve Mental help and her company was sunk. Chance was asked to consult on Nygma's case by Dr. Burton after she was told that she had screamed for hours that he knew who Batwoman was. After she wondered if the Riddler had indeed remembered the information that was taken from Bryce's brain that concerned Batwoman's identity, Chance went to her cell. Chance identified himself and then asked Riddler if she remembered him. When she answers affirmatively, the Riddler offered to reveal the identity of Batwoman to Chance if she said "please". Chance did so, and the Riddler responded by telling her that she herself was Batwoman, and as if to prove her point, he started to flap her arms as if to imitate a bat while she laughed maniacally; her mental state was scrambled upon the brainwave hub's destruction. At that point, Chance came out to tell Bryce that hes secret was safe, and confirmed that Nygma was now a complete lunatic.
=== Legacy ===
Riddler's jacket and derby hat were kept at Arkham's Criminal Property Locker, along with one of Two-Face's jackets and slacks. A few years later Bane and Poison Ivy caught a glimpse of Nygma and Dent's custom clothing when they stole Victoria Fries' cryo-suit from the guards. This seemed to make little to no impact on the pair.