The Riddler
In Detective Comics #140, co-creators Bill Finger and Dick Sprang introduce the Riddler as a puzzle expert out to baffle Batman with a series of perplexing plots. Challenging the dynamic duo to a deadly game of wits, Riddler takes control of a giant crossword puzzle before leading Batman and Robin into a booby-trapped maze of doom rigged to explode with a bomb.
The Riddle-Less Robberies of the Riddler
Frustrated by his psychological compulsion to alert Batman and Robin to his crimes with riddles, the Riddler attempts a theft without leaving his trademark clues in Batman (Vol 1.) #179. Unable to rob without riddles, Riddler subconsciously leaves behind seemingly unconnected clues. Batman and Robin’s deduction leads them to a safe at a glove factory, thwarting the Riddler’s “least dangerous robbery of all: a ‘safe’ robbery.”
Riddler on the Rampage
After a plot to blow up Gotham City fails because of his compulsion for clues (Detective Comics #362), Riddler realizes how to defeat Batman: by flooding the Dark Knight with riddle-clues in an attempt to drive Batman insane. Batman and Robin race to crack an elaborate series of unending riddles, each more dangerous than the last, a trail of traps leading them to “a riddle without an answer”: a riddle by itself (Batman #279).
The Oldest One in the Book
After escaping from Arkham Asylum, Riddler reveals a change to his game with Batman: Riddler renounces crime and leaves complex clues leading to other criminals in Batman: Gotham Adventures #11. In trying his hand at Batman’s detective game, the Riddler thinks he’s figured out a way to challenge Batman without putting himself in danger. But Batman outsmarts Riddler by figuring out the first recorded riddle in history: the oldest one in the book.
Riddles
Released from prison, Riddler leaves Gotham for Hub City, home of the detective vigilante The Question. After Riddler hijacks a bus and threatens to kill passengers who fail to solve his riddles, The Question outsmarts and stumps the Bat-villain with complex philosophical riddles and trick questions. Asked about everything from abstractions to seventeenth-century metaphysicians to the benevolence of the universe, the Riddler suffers a nervous breakdown to end The Question #26.
The Primal Riddle
In Batman: Legends of the Dark Knight issues #109-111, Riddler challenges Batman to solve his “primal riddle,” but Batman is nearly killed after a shock from a power grid. The blast bizarrely transfers Batman’s spirit into Riddler’s body, which nearly drives the villain mad by asking overly simple riddles. In search of the missing part of his soul, the conundrum draws Batman to the “ultimate death trap”: an electrified chamber where Batman will either drown or be electrocuted. Escaping the pit as half-Bat, half-man, Batman beats the Riddler once more — after some soul-searching.
Batman: Hush
When investigating the identity of masked villain Hush, Batman falls prey to a conspiracy between the Riddler and his childhood friend, Thomas Elliot, in Batman: Hush. After plotting to figure out Batman’s secret identity (in Catwoman: When in Rome), Riddler deduces Bruce Wayne is Batman and masterminds an elaborate plot involving villains Joker, Harley Quinn, Scarecrow, Clayface, and Poison Ivy. Riddler figures out the face beneath Batman’s mask, but addiction to riddles prevents him from revealing Batman’s secret: “A riddle that everyone knows the answer to is worthless.”
Batman: Earth One (Volume 2)
In Batman: Earth One (Volume 2), the clue-obsessed and egomaniacal Riddler is an anarchist and serial bomber terrorizing Gotham City six months after Batman’s first case. Batman investigates the murders of 43 serial killer victims, deducing Riddler’s seemingly random acts of violence are actually targeted killings — part of a cover-up involving the associates of corrupt Gotham City Mayor Oswald Cobblepot.
Under the Gun
Puzzled by a thought experiment — “The Flash is faster than a speeding bullet, so how do you stop him?” — Riddler holds Central City hostage with an army of weaponized drones in The Flash #50-52. Unable to resist the challenge of beating the Flash’s speed with just the power of the mind, Riddler reveals his most ambitious plot yet: threatening to use the rogue Heat Wave as a nuclear weapon to destroy Central City.
Dark City
Set in Bruce Wayne’s first year as Batman, Zero Year re-imagines Riddler as an ex-Wayne Enterprises employee on a mission to make Gotham City “smarter.” The newly revealed Riddler plunges Gotham into darkness before taking control of the city’s power grid, flooding Gotham and holding its citizens hostage with balloons filled with lethal chemicals. Turning Gotham into his deadly playground, Riddler rules over the savage city with a challenge: outsmart the Riddler with a riddle, save Gotham. Trapped in a rigged game of life or death and tasked with solving 12 riddles, Batman wins this war of the mind — with a punch to the face.
