riddle me this

personality

From the get-go, the things most apparent and on-its-face about Edward are his pompous, grandiose sense of self-worth and his jovial extravagance. Arrogant, egotistical, and incapable of accepting himself as anything but the most brilliant, it’s unfortunate his remarkable intellect comes shackled with an insufferable hubris. Fortunately for the rest of Gotham, that hubris leads to his downfall.Still, Edward Nygma is a very real threat. So consumed by his obsession for attention, validation, and proving his own intellect, he has a long, stained track record of devising traps and riddles, imprisoning his victims as pawns in his deadly games against a hero, namely Batman. Worse yet, he doesn’t even consider these to be crimes or murder — if they were just a bit smarter, they wouldn’t be in the situations they find themselves in — and their deaths and defeat are used for his ultimate goal: to reinforce his sense of superiority. But make no mistake. Edward, while plagued with a delusional sense of self-importance, is debilitatingly insecure, and his uncontrollable compulsion for proving his own intelligence is paramount in his life. It will never be enough.

Positives: Observant, dedicated, clever, deductive, persistent, independent
Negatives: Egotistic, arrogant, immature, short-tempered and petty, indignant, resentful
Alignment: Lawful evil
Temperament: Choleric-sanguine
Enneagram: Type Three - The Achiever (Level 9)
Mental Health and Personality Disorders: Severe obsessive-compulsive disorder (OCD) and narcissistic personality disorder (NPD). He has periods of emotional instability and, while he is not as physically violent as the other members of the Rogues' Gallery, he is volatile, dangerous, and has shown that he is more than capable of ferocious brutality.

modus operandi

Edward has a compulsive need for leaving behind clues, often in the form of riddles, to his crimes. In this way, he's challenging the intelligence of those he's selected as an opponent. This does not mean he sees them as an equal. He does not.The Riddler does not often kill and causing bodily harm is never his endgame or goal. Any injury or death that may be a result of his crimes is more or less a side effect, though he may perceive it as inevitable. His one true goal is always about proving his intelligence and outsmarting someone, specifically Batman.His crimes include, but are not limited to, blackmail, assault, burglary, armed robbery, manslaughter, homicide, kidnapping/abduction and hostage-taking, and various cybercrimes including hacking the stock market.

background

Childhood
+cw: child abuse

Edward grew up in a house of terror. His mother was never in the picture; his father, an abusive, raging beast. He went to bed black-eyed more than once, swollen and purple, and limped to school where he was tormented by the other kids.One day, he entered a school contest, young Edward so bright and brilliant, earning first place. His father was convinced he cheated and beat him to a pulp. Punched, kicked, bloodied and bruised, aching and hurt, for years, Edward learned a constant, perpetual lesson: the strong will always prey on the weak, and his father will always think of him as a moron, capable of nothing and worth absolutely nothing to no one.It is during Edward’s childhood that he begins developing a lifelong obsession with proving his intellect, in outsmarting everyone and never telling a lie. This fixation crops up in his love for riddles, puzzles, and games… something that will never die away.

Origin of the Riddler (Zero Year)
[note: Though I use Zero Year, I'm more than happy to be compliant to other Batman origins i.e. Year One. Likewise, aside from the events of Zero Year, I do not use New 52.]

Edward grows into a man. He has his humble beginnings as a scam artist, then, in computer forensics amassing intelligence for blackmail, then, eventually, as a strategist and advisor for the auspicious Philip Kane, who was at the time in control of the famous Wayne empire, and billionaire Bruce Wayne's uncle. Kane had chosen to ignore Nygma’s shady past. A grave mistake.With the surprise return of Gotham’s son — Bruce was believed dead before — Edward advises Philip to kill his young nephew, masked as an accident or misfortune, to garner public sympathy all to improve Wayne Enterprise’s less-than-favorable image, and to eliminate Bruce as competition. Philip discards his advice, and Edward lets slip the dogs of war. A group called the Red Hood gang, sent by Nygma, corners Bruce with a botched murder attempt, blowing his brownstone up in a plume of fire. Philip puts two and two together and holds a gun to Edward’s head. Edward escapes.Shortly after, Nygma flashes on a wide screen in Gotham City, masked and decked in green. “Riddle me this, Gotham!” he shouts, bright-eyed and brilliant. “There are two sisters. Each gives birth to the other. Who are they?”The answer: Day and night.He shuts Gotham down in a total, impenetrable blackout, and the Gotham City Police Department, desperate to restore power before a superstorm slams the coast, plays right into his hands. Nygma waits for them to fix it. They do. And alerted, in control of the power grid, Edward sets off an explosion, blowing up Gotham’s retainer walls and setting a catastrophic, monstrous flood loose, wiping out the city.Edward claims this is his way of weeding out the dumb from the smart, to leaving only the brilliant. He marks this a new year. Zero Year. In time, with the help of the GCPD and an old friend named Lucius Fox, the mysterious Batman, in reality Bruce Wayne, is eventually able to track down Edward’s location. He solves all of the Riddler’s riddles. He pommels the man to a bloody smear. He seizes the power grid from him, gives it back to Gotham, and crushes Edward’s stronghold of terror to ashes. At last, after a month of total and frightening darkness, the city can heal.Nygma is too dangerous and “mad” to be housed in Blackgate Prison. He is sent to Arkham Asylum, a place he will be more familiar with than any man should.

Life of Crime
(The Long Halloween, When in Rome, The Riddle Factory, The Batman Chronicles #3: Riddle of the Jinxed Sphinx, Hush, and Arkhamverse including Batman: Assault on Arkham, Batman: Arkham Knight - The Riddler's Gambit, and the Arkham games)
+cw: cancer

After Zero Year's failure, the Riddler continues his marred and troubled life of crime, foiled time and time again by the Dark Knight. He has worked with Carmine Falcone, Gotham's largest mob boss, to uncover the identity of serial killer Holiday. He's aided Catwoman, or Selina Kyle, in Rome, attempting to dig up the truth about her past and family. He's robbed. He's killed. He's hosted a lethal riddle gameshow on live either-late-night-or-too-early television.Eventually, however, even Edward's presence begins to wane. He fades into the background. New criminals crop up. One day, with rain pouring and the world going tinny in his ears, world-renowned neurosurgeon Doctor Thomas Elliot tells him he has an inoperable brain tumor. Cancer.But miraculously, Edward beats it. He finds the location of an untouched Lazarus Pit, a naturally occurring bath of chemicals that can restore the dead back to life with one major setback: it drives anyone who goes in it mad. It gives Riddler clarity, though. He deduces that Batman, Gotham's Dark Knight, their one and only true Caped Crusader, is actually billionaire playboy Bruce Wayne... And he learns something else, too.Doctor Thomas Elliot was Bruce's childhood friend, who's despised him since the day Bruce's father saved his mother from a supposed-to-be-fatal car accident, barring Elliot from immediate inheritance. The Riddler exposes Batman's identity to him. Elliot picks up the mantle as Hush to enact revenge. The two join forces, unexpected bedfellows, in bringing the vigilante down.But the plan fails. After siccing Hush onto the Batman and nearly killing him — Elliot's identity was hidden and muddied by bringing in Bruce's enemies and friends into the mix as red herrings, planting seeds of doubt within his own ranks — Batman is eventually able to learn Hush's true identity and the mastermind behind the whole master scheme. He captures Elliot. He confronts the Riddler. Edward reveals he had cancer, cured by the Lazarus Pit, and Batman pulls out two trump cards: Edward won't ever expose Bruce's identity to the world because a riddle that everyone knows the answer to is worthless, and now aware that Edward had used a Lazarus Pit, he could tip Ra's al Ghul off, the leader of the League of Assassins and the recognized owner of these pits. It would put Edward in their deadly crosshairs.It's a stalemate.As is his wont, Edward continues his seedy lifestyle, returning to more cyber roots. He is able to horde a wealth of destructive blackmail material and intends to let the cat out of the bag on Christmas day, promising a chain of events that will lead to Gotham's final fall. He's stopped. He's sent to Arkham Asylum. He escapes. He eventually falls under the boot of Amanda Waller, director of the shady government organization A.R.G.U.S., and is forced to become a part of her so-called Suicide Squad with a detonating device implanted through the back of his neck. Edward is as smart as he is wild, though. He fries it via self-electrocution and escapes, and Waller, at a later date, captures a new team and gives her criminals-turned-government-pawns a directive: kill the Riddler and obtain his cane, which she believes may contain data about the squad that he himself hacked and extracted. She doesn't count on Nygma turning her pack to his side by disabling their bombs, though, or in Batman swooping in and thwarting her plans in having both Nygma and the Suicide Squad killed.Everything blurs after that. Edward is thrown to Arkham Asylum. Edward breaks free. Edward captures hostages, using them in his deadly riddle games against his lifelong nemesis Batman, and after each soul-crushing defeat, battered and humiliated, he grows more and more desperate, unhinged, and obsessed, a tarnished shell of his former self.Officer Cash of the GCPD notes that Edward's rants are no longer funny. He's broken, and Batman broke him.The events of Arkham Knight unravel. Supervillain Scarecrow, or Jonathan Crane, intends to unleash a cloud of fear toxin across the entirety of the East Coast. In order to save GCPD Commissioner Jim Gordon and his pupil Robin, held hostage by Scarecrow, from certain death, Batman reveals his identity to the whole world. He defeats Scarecrow eventually. Then, mysteriously, he dies in a freak explosion set upon Wayne Manor.

Private Investigator
(Detective Comics #822, 824, and 828, Batman Confidential #26, 27, and 28 [he's not working alongside Batman/the GCPD as an inmate, but reformed and free], and Gotham City Sirens)
[note: My default is that Infinite Crisis #7 did not occur and Edward was never struck by Shining Knight, sending him into a coma and "curing" him of his OCD. Edward becomes a P.I. after the events of Arkham Knight.]

The Batman is dead, and with him, so is Edward's all-consuming obsession in beating him. He is set adrift. His purpose in life, scrambled. Nygma is aimlessly forced through the revolving doors of therapy, having no more reason to break free, and eventually staggers out of a psychiatric hospital one last time, finally and at last legally "sane".He starts his own private investigation firm, sanctioned due to his great intelligence, and even proves a valuable asset to the GCPD. Edward Nashton is no longer Nygma or the Riddler and, admittedly, may struggle in his day-to-day life. His OCD is still prevalent but is better managed and no longer so connected to a propensity for crime.