What needs to be sharpened like a blade but is made out of fat and electricity? The human mind. With that little quandry as a starting point to help set the scene, it is time to discuss Edward Nygma, or as he's better known, the Riddler.
Nygma is the smartest enemy in Batman's rogues gallery, keeping the Dark Knight's mind sharp as a well-honed Batarang. He is a mastery not just of puzzles, but strategy, computer languages, logical systems, engineering, forensics, and several other fields of study. He also has an obsessive compulsive nature which compels him to leave riddles whose answers will allow others to solve the crimes he commits, buy few are smart enough to keep up. Here are ten times Riddler's outsmarted Batman:
10 Making His Mark During Zero Year
When Scott Snyder took over writing Batman during DC's The New 52, he originally planned to build upon the established Batman continuity. However, DC editorial required him to write a new Batman origin story. The result was Batman: Zero Year, a bright-colored tale exploring how Bruce Wayne became the Batman.
This wild thrill of a sci-fi romp featured many Batman villains --both classic and obscure-- but the main villain is Riddler, who successfully plunges Gotham City into an apocalyptic state, effectively taking over the whole city with an army of weaponized drones while making the citizenry completely dependent upon him. Batman eventually bested him but by then, Riddler had forever left his mark on Gotham.
9 Prison Break in Forever Evil
One of the big events of The New 52 was Forever Evil, in which the evil version of the Justice League from another reality took over the Earth, while a team of villains banded together to defeat this new foe. During a massive prison break, Riddler proved that he was able to out-think most security systems that Batman and the rest of Gotham's law enforcement community thought could hold him.
Beyond all this, he invented new riddles just to align with his escape, then beat the ever-living snot out of an abusive guard who had earned Riddler's ire. His cruelty may be questionable, but no one can question his motives or his results.
8 Prison Break in Death of the Family
During Death of the Family, the Joker attacked the different members of the Bat Family, reasoning that they were holding Batman back, and if Batman was ever to be set free, first Batman would have to lose all the people he loved. During an attack on Arkham, Joker stopped outside a cell to talk with an inmate: the Riddler.
Joker threw a gas grenade into Nygma's cell, telling the master of riddles that if he did not break out in two minutes, he would die. Riddler easily escaped, informing the Joker that there were forty-six ways to break out of his cell, three of which could be achieved in under two minutes. As it turned out, Riddler could always get free and was just waiting to account for a recent shift in the guards' rotations. Joker forced his hand and nearly killed him, but the two still teamed up to defeat Batman.
7 Defeating Batman in Death of the Family
While Death of the Family is all about Joker's master plan to sadistically torture, flay, and kill every member of the Bat Family, he is not the only villain to be involved in the planning. As Joker himself tells Batman, Edward Nygma is "your strategist, the man who keeps your mind sharp."
The sharp-minded strategy involved in Joker's takeover of Arkham includes taking civilian hostages and dressing them as the Justice League members, then killing them in front of Batman, all to psychologically manipulate the Dark Knight. It also involves dressing prison guards as the Joker and Batman and forcing them to dance, installing surveillance systems, and coordinating multiple ambush points throughout the Asylum. Joker enjoys such sadism, but Riddler is the mastermind capable of making these horrors a reality.
6 The Hush Heist
Batman: Hush is considered by many fans to be one of the greatest Batman stories of the 2000s--no small feat, considering the many great writers to tackle the character during that decade. As all of Batman's rogues begin attacking him in what seems to be a coordinated conspiracy, Riddler is seemingly left out, as is made clear when the Caped Crusader stops Nygma and his henchmen while they are robbing an armored truck of all things.
Of course, Edward Nygma is smarter than all those other villains whose strings are being pulled because, as it turns out, he is the one who has been the puppet master all along. Not only does he put Batman through the ringer, but he convinces Gotham's greatest detective that he's innocent.
5 Figuring Out Batman's Secret Identity
One of the most harrowing scenes in Batman: Hush involves the Dark Knight confronting Jason Todd, who had been dead for years. However, the former Robin's grave has been exhumed in the Wayne Family Cemetery. This means that whoever opened the grave and set Jason against him has learned the fact that Bruce Wayne is really Batman. If it was not obvious already, it was the Riddler who figured this out.
Edward Nygma has been dying of cancer and ended up using one of Ras al Ghul's Lazarus Pits. During the process of being resurrected, his mind became even sharper than usual and in this temporary explosion of mental acuity, he worked out Batman's secret identity.
4 Devastating Gotham in The War of Jokes & Riddles
When writer Tom King began his Batman run, it seemed like he could do no wrong. His stories grew increasingly inventive as he dealt with issues of mental health, personal legacy, and even incorporated various forms of spoken word poetry into the dialogue. Then he enraged fans with a shocking plot twist so they rudely flooded him with death threats.
But in between these two points, King wrote a single masterful story which was heralded as his crowning achievement: "The War of Jokes and Riddles." This story is all about a feud between Joker and Riddler which escalates into an all-out war, tearing Gotham asunder. No matter what Batman does, he can't stop the two factions from fighting, so in the end, he joins forces with the Riddler, knowing that the only way to end the war is for one side to beat the other.
3 The War's Final Punchline
Not only does Riddler force Batman to join forces with him in "The War of Jokes and Riddles," but he also pulls a con on Batman. The whole war, which killed hundreds of people and tore Gotham asunder, was the Riddler's idea of a joke to make the Joker laugh.
As Riddler tells Batman, "Not every story is your story. You really think it bothers me you're alive? I could kill you. Easily ." Riddler then goes onto explain his motives, saying, "I keep you alive for the same reason we all keep you alive... You're not a challenge. But you're fun." Joker, on the other hand, was a challenge, which was all the motive Nygma needed.
2 Working with the Designer
Recently, writer James Tynion IV took over Batman and introduced new villains, among them a criminal mastermind who worked with Catwoman, Joker, Penguin, and Riddler at some. This villain is called the Designer, because of his intricately complex designs behind executing the perfect crimes.
The Batman did not even know the Designer existed, but Riddler established contact with this individual and worked to become an even better villain. Then the Designer worked with Joker, who was such a psychopath the whole operation exploded, but that doesn't invalidate Riddler's achievements here.
1 Clearing Bruce Wayne's Name
Billionaires have immense power, and they also abuse this power... a lot. After all, what better example of abuse is there than a billionaire spending his fortune on cool gadgets to beat up poor and mentally ill people every night?
In the fantasy world of DC Comics, when Bruce Wayne is accused of murder, he is actually punished for his unchecked privilege getting someone else killed. Of course, Bruce Wayne didn't kill the person and he is found innocent... but only after Edward Nygma, of all people, clears his name.