The Riddler, aka Edward Nygma, has earned the reputation of being Batman‘s smartest villain (even though it’s really Mister Freeze). Over the years, the Riddler has displayed a deep well of technical knowledge, inventiveness, and analytical thinking. On top of that, he has his cache of trivia and general knowledge which he uses in his riddles. All of this has been used to challenge and test the Batman, and, many times, it’s pushed him to the brink.
With that in mind, let us look back on the most genius moves ever made by the infamous Riddler over the years–as well as some of his dumbest decisions.
10 GENIUS: Kicking Off Zero Year
During Scott Snyder and Greg Capullo’s Batman “Zero Year” storyline, it’s revealed (or, rather, retconned) that the Riddler is the first costumed foe that the Batman faced. More than that, the Riddler beat out Batman twice before shutting down all power to Gotham City so that only the most clever survive.
In essence, at the beginning of both’s careers, the Riddler beat Batman and unleashed an apocalyptic event upon Gotham City. He runs Gotham during Zero Year and keeps out of the reach of Batman. He is eventually defeated of course, but he had a good run here.
9 DUMBEST: Trying To Set Up A Riddle During Knightfall
One of the more laughable moments for the Riddler is his attempts to set up a riddle for Batman and the GCPD during the dramatic events of “Knightfall.” For the uninitiated, Knightfall is the iconic story in which Bane breaks Batman’s back.
During this period, Arkham Asylum was busted open by Bane, and all the inmates were running rampant in Gotham. Riddler and his henchmen set up a trap for Batman and the police, but both were too busy with the numerous other threats enveloping Gotham. In the end, Nygma’s henchmen abandoned him and took the loot.
8 GENIUS: The Primal Riddle
In a story in Batman: Legends of the Dark Knight, the Riddler presents his “Primal Riddle.” This was intended to be a deathtrap that left Batman with two options: drown or die by electric shock. There was no out, no solution, and no escape. The Riddler would simply kill the Batman in a manner theatrical enough for his own tastes.
Unfortunately, Batman still found a way out and took down Nygma, but this showed a surprising break from the Riddler’s usual need to actually provide a solution for his foe.
7 DUMBEST: Trying To Cooperate With The Joker
During the recent “War of Jokes and Riddles” storyline in Batman Rebirth, the Riddler attempted to make an alliance with the ever-mercurial Joker. In the Riddler’s mind, neither villain had been able to defeat Batman on their own, and both would be dissatisfied if the other were solely responsible for Batman’s death.
Logically, the two should team up and become a force that even Batman could not overcome. The Joker is anything but logical, so he shot the Riddler to see if it would make him laugh. It surprisingly didn’t. The Riddler recovers, and the two villains begin their war that almost razes Gotham to the ground.
6 GENIUS: Solving The Conundrum
For a short while, the Riddler was actually reformed. A blow to the head from the Shining Knight shifted Nygma’s brain chemistry in such a way that he was cured. During this time of good intentions, the Riddler found himself at the mercy of the villainous Conundrum. This rogue modeled herself after the Riddler and took him and a famous writer hostage.
The Riddler immediately deduces that Conundrum and her henchmen are police science students in college and are trying to “fill the void” left by the Riddler. Eventually, the Riddler is able to signal Batman for help, and the Dark Knight saves both Nygma and the writer.
5 DUMBEST: Failing To Identify The Holiday Killer
One of the Riddler’s “earlier” failures is his inability to identify the Holiday killer in Batman: The Long Halloween. He bragged about his ability to identify Holiday, but he couldn’t quite hack it.
He was tasked with doing so by Carmine Falcone, and the Riddler tested Falcone’s patience by accusing Carmine himself of being Holiday. He was later targeted by the Holiday killer, but the killer spared Nygma.
4 GENIUS: The Metal Maze
During the Dark Nights: Metal storyline, the Batman Who Laughs, a villainous version of Batman from the Dark Multiverse, gives the Riddler a card that grants him greater power. With this power, the Riddler created a vast labyrinth keeping any outsiders from entering Gotham City.
3 DUMBEST: Teaming Up With King Tut
In Year of the Villain: The Riddler, we learn that Lex Luthor neglected to pass out the gifts of Perpetua to the Riddler, and, at this point, the Riddler was frequently cooperating with King Tut.
Their failures to beat Batman were getting more and more pathetic, and Lex Luthor confronted Nygma with why he didn’t receive a gift. Luthor viewed Nygma as a man constantly hamstringing himself, and this motivates the Riddler to abandon Tut and start a new phase in his life.
2 GENIUS: Discerning The Batman’s True Identity
During the now-legendary “Hush” storyline by Jeph Loeb and Jim Lee, the Riddler teams up with the mysterious Hush to bring down the Batman. The Riddler helped Hush lay out many of his schemes and even informs Hush of Batman’s secret identity as Bruce Wayne.
When it’s all said and done, Batman confronts the Riddler about this, and Nygma brags about it to the Dark Knight.
1 DUMBEST: Allowing Batman To Make Him Too Afraid To Use It
Disappointingly, Batman talks the Riddler into not doing anything with the knowledge. Batman tells the Riddler that there’s no value in a secret shared with others, and the knowledge of Batman’s secret identity is only valuable if it remains a secret. The Riddler is dumbfounded by this and realizes he can’t do anything with the secret identity.
Now that everything has been rebooted by Flashpoint, it seems that the Riddler no longer knows that Bruce Wayne is Batman.
As one of the most intelligent villains in Batman's rogue's gallery, the Riddler has some good plans. However, not all of them are good.