History: (Batman I #171 (fb)) -As a boy Eddie Nashtron won a jigsaw puzzle contest at school by breaking into his teacher's desk and photographing the assembled jigsaw puzzle the day before the contest. As an adult he ran a crooked carnival puzzle game, but this wasn't satisfying enough for him. He changed his name to E. Nigma and took on the costumed identity of the Riddler, committing daring crimes, then leaving riddles at the scene of the crime to taunt the police. He became an arch-enemy of the Batman.

(Batman I #171) - Riddler was paroled and told Batman and Robin he'd gone straight, offering to help them capture the Molehill Gang who'd been foiling them. Batman was suspicious about Riddler changing his nature, but accepted his aid anyway. The Molehill Gang operated out of the sewers, popping out of manholes for robberies, and then escaping into the winding tunnels beneath the city. Riddler learned their location from his jailhouse friends, and led the Dynamic Duo to their lair. The gang's lair was rigged with spring-loaded manholes and cables, but the heroes overcame them and apprehended the crooks. Two days later Batman and Robin were honored guests at the Police Athletic League picnic, and in their picnic basked Riddler left a clue, "What's the longest word in the world," and the solution was "smile" because there was a mile between the first and last letters. Batman deduced that Riddler had returned to a life of crime, and was going to rob millionaire "Smiles" Dawson. They saw Riddler running away from "Smiles" yacht with the prized black pearl of the Pacific, and when they tried to apprehend him his trunk popped out puzzle pieces that entangled them. They did catch Riddler, but it turned out he'd bought the black pearl fair and square with his uncle Edward's inheritance. "Smiles" had a riddle left behind by Riddler, "Why is an orange like a bell?", and Batman came up with the answer both must be peeled / pealed. He figured Riddler would target the Peale art gallery, and saw Riddler holding a gun to Peale, taking an ivory-and-ruby cross. The gun turned out to be a lighter, and the cross another purchase, but Riddler told them he'd already given them a clue as to what his master plan was. Robin guessed that the purchased items were black, white, and red, which referenced the riddle whose answer was "a newspaper." Batman figured out that that answer was too obvious for the Riddler, and because the pearl was shaped like an "O" and the cross like an "X" he'd try to rob the Western-themed Ox Club. Riddler was indeed casing the joint, revealing that he only pretended to be a changed man to keep Batman guessing, and he'd only helped catch the Molehill Gang so the Dynamic Duo could focus all their attention on him. He activated his costume's defenses, and it shocked the heroes to the touch. Batman and Robin struck his head, causing him to spin like a top, but not injuring him. Batman realized he'd turned on the defenses by pressing one of the question marks on his costume, so Batman pressed it again to deactivate the defenses, and knocked Riddler down with one punch.

(Batman I #179) - Riddler escaped from prison by carving a skeleton key, and resolved to stop leaving riddles so he'd stop getting caught. He tried to commit a jewel heist, but couldn't bring himself to finish because he hadn't tipped his hat to Batman with a trademark riddle. Riddler couldn't bear a life without crime, so he began studying psychoanalysis, so he could condition himself out of his riddling compulsions. Days later he robbed the Yab Soda Company's antique coins, and was thrilled that he'd overcome his weakness. Gordon reported the crime to Batman and Robin, but were baffled by the change in Riddler's MO. Batman deduced that he had sent riddles, but very surreptitious ones. In the past few days Batman had received a 9 inch blank letter, a honeysuckle plant, and seen the state of Minnesota painted in a bank. Minnesota was "the state where you could always get a soda," a nine inch letter was "Y" because it was one forth of the word yard, and the honeysuckle was like the letter A because it was always followed by a "bee." The clues spelled out Yab and pointed to the soda company, so Batman had Gordon report any hidden clues to him over the next few days. Three strange advertising stunts were clues that led Batman and Robin to the Corsican Glove Factory, where they caught Riddler red-handed. Riddler realized that he hadn't cured himself, when he slept he went sleepwalking setting up clues for the Dynamic Duo. He admitted he couldn't overcome his compulsion, but told the heroes he'd merely devise more clever riddles they couldn't crack.

(Batman I #317) - Riddler broke out of prison, and knowing he still had a compulsion to send Batman riddles before committing crimes he sent him a book entitled “1001 Riddles For All Occasions,” hoping to throw him off by sending clues for his next possible 1001 crimes. Riddler robbed a poultry truck, and then set the chickens loose on a magazine distribution warehouse to make off with their magazines. His former cellmate Jake Hammer was a gun-runner, and Riddler decided to take his place. The magazine warehouse was a front, and the magazines were hollowed out and filled with firearms. He met Hammer’s contact at Gotham Harbor, but the man was upset that Riddler was selling him guns and not his known contact. Batman and Robin showed up on the scene, telling Riddler they’d virtually ignored his book of riddles, instead choosing to do detective work and interview Riddler’s cellmate. Riddler grabbed a firearm from his stash and tried to gun them down, but Batman caught him in a cargo net. Batman annoyed him by riddling him “Why are you like a spawning salmon.” The Riddler knew the answer was that he was going up the river.

(Question I #26) - Gordon solved one of Riddler's latest clues while the rogue was in prison. He visited Joker in his cell to tell him he was being released because he hadn't been read his Miranda Rights, and the DA didn't think he was worth the time. Gordon told him he was a has-been, having run out of clever riddles, and advised him to find a new career. Riddler caught a bus to Hub City, where he met fellow ex-con Sphinx Scromuliski, and they hit it off. She told him she was going to rob the bus, and he'd given her an idea with his modus operandi. She shot anyone who couldn't answer Riddler's riddles, getting the immediate attention of their fellow passengers Question and Aristotle Rodor. Question got Riddler's interest by reciting John Donne's "Song," and berated Riddler for using puerile puns as riddles. He asked metaphysical questions, such as why a benevolent God allowed suffering, if God existed, and if he didn't why religion was ingrained in every major culture. Question snagged Sphinx's gun, and she fled the bus, falling into a freezing river and drowning. Riddler, Question and Tot huddled around a barrel fire, and Riddler admitted he told riddles because the questions that plagued the Question drove him to near madness as well. In the Christmas spirit the Question said he'd let the Riddler go before the police arrived if he could answer the Question's riddle, and the Riddler was game.

(Impulse #48) - Riddler was looking to avenge himself after a defeat by Flash, so he targeted Impulse, kidnapping Max Mercury and Professor Morlo. Riddler told Impulse he'd hidden three bombs around Manchester, and Impulse would have to solve a series of riddles to find them. Impulse got bored with the riddles, so he ran around Manchester at superspeed until he found and defused the bombs. Riddler was supremely annoyed that Impulse wouldn't play his game, and Impulse handed him over to the police.

(JSA #28) - Nevada; Riddler went to Roulette's House to attend one of her gladiatorial contests. He was among the crowd of villains that watched members of the JSA forced to fight each other.

(Green Arrow III #12) - Riddler and his crew robbed a restaurant, and he admitted this wasn’t a big job for him o he’d limit the banter and riddles. Green Arrow and Black Canary were eating at the restaurant, and they quickly took Riddler out.

(JLA #63) - When Wonder Woman’s lasso, the embodiment of truth, broke because she doubted it, the truth became subjective, altering the world. Riddler could no longer understand his clues, and Batman easily captured him.

(Green Arrow III #35-37) - Albert Davis hired Riddler to steal a number of mystical Russian artifacts from the Grell Museum in Star City, and Riddler agreed, but point out that he was no common criminal, and that he would also commit distraction crimes that appealed to his sense of whimsy. After completing the job for Davis he painted an art restoration lab blue, hog-tied the Star City Rockets baseball team and filled the financial center Montrose Tower with dried prunes. Davis disapproved of his theatrics, so Riddler choked him a bit with his cane before concluding their business. Riddler acquired an atom bomb, and announced to Star City that he would be detonating it. He cut off all exits to the city and holed up in the Tinder-Smith Garden arena, booby-trapping it so well even Green Arrow couldn't get inside. He demanded a ransom of $100,000,000, but the power went out in the city, and all mechanical devices stopped functioning because Mr. Davis used the stolen Russian artifacts to cast a spell over Star City. Green Arrow took this opportunity to take down Riddler, and he was imprisoned. Davis' spell also summoned demons that killed anyone breaking any laws or acting out in any violent fashion, Davis' idea of a perfect society because his wife and children were killed in a carjacking years ago. Green Arrow wanted the name of Riddler's employer, and refused to play word games with the villain. He beat on Riddler until he gave up Davis.

With the help of Hush, Riddler deduced Batman's identity, but refused to share it with other criminals.

(Green Arrow III #49, 50) - Riddler, contracted by Brick, had Arsenal kidnapped by Drakon and brought to his safehouse, Puertas al Infierno, a former prison, and left a taunting riddle for Green Arrow. The Outsiders and Team Arrow stormed the safehouse, defeating Riddler’s hi-tech armored mercenaries. Riddler caught Green Arrow and shot him in the shoulder as payback for the brutalization Arrow’d put him through. Once Riddler learned his security had been breached by the Outsiders he fled, noting that his act was a game, and a hint of things to come when he was serious about destroying Green Arrow.

(Villains United: Infinite Crisis Special #1) - The Society made plans for a worldwide prison break to free every incarcerated supervillain, and they sent Killer Croc to free Arkham Asylum's inmates. Riddler was one of the released inmates and after the prison breaks Riddler and the escaped villains massed in Metropolis. They were confronted by an army of virtually every hero on Earth, and the heroes and villains engaged in an epic battle.

(Batman I #705-707) - Riddler met his supposed daughter Enigma, and brought her along on a case. They ransacked the home of Lucius Fox for computer files on the Jade Compass Society, and when Batman interfered they attacked him. Enigma wanted to kill Batman, but Riddler warned her that if anyone did that, it would be him. Batman summoned Robin, and they forced the villains to flee. Riddler and Enigma presented the computer files to their employer, a woman flipping a scarred coin. Riddler was happy with his payment, but she’d also promised him the files on him from the D.A. office, the only prize that motivated him to do monkey work that he saw as beneath him. She promised she’d hand over the files after Riddler and Enigma did one more job.

Comments: Created by Bill Finger &  Dick Sprang