75 Years of The Riddler

Batman faces many villains with serious, even angry demeanors, which makes the Riddler standout for his comical antics and style. The Riddler is a villain who delights in his naughty schemes. His obsession with solving puzzles is what defines Riddler’s criminal career as he habitually leaves puzzles and riddles as his calling card. What sometimes appear as innocuous brainteasers have clues nestled within to taunt Batman and the Gotham police.

On the occasion that he does best Batman, it usually involves putting the Caped Crusader in complicated death traps to further test him. As a fan of magicians, the traps Riddler lays for Batman typically have an abundance of flair and accoutrements, which provide Batman with the loopholes to escape. Riddler’s compulsion for traps and the need to prove he’s smarter than others are usual the factors of his downfall.

The Prince of Puzzles made his debut in Detective Comics #140 (October 1948), created by Bill Finger and Dick Sprang. Introduced as Edward Nigma (later Nygma or Nashton), the Riddler’s origin started with a school puzzle contest he became obsessed with winning to the point of cheating to ensure his victory. His newfound passion for puzzles grew and after leaving school he became a carnival performer, running a rigged puzzle game.

Wanting greater thrills and challenges, he became a fulltime criminal. During his first encounter with Batman and Robin, Riddler tried to stump them through riddles laced with double entendres. He traps them in a maze on the pier, but they escape before an explosion occurs, and Riddler seemingly vanishes.

It’s revealed that he survived in Detective Comics #142 (December 1948) when he resurfaces to steal the prize money from a puzzle contest. Riddler then creates his own contest with clues that involve a skyscraper and a blimp towing a puzzle.

Riddler’s silliness was on full display in Batman #171 (May 1965) when he tells Batman that he’s reformed, then attempts to discredit Batman and Robin with riddles that lead them to find Riddler conducting legal business. When Batman finally catches him committing a crime, the Riddler uses a device that makes him like a roly-poly toy in a failed attempt to avoid capture.

The 1989 Secret Origins Special sees a film crew working on a documentary about Gotham’s costumed villains who interview Riddler as an elderly man. He pesters the crew with junkyard props and silly riddles while attempting to refrain from revealing actual details about his own origins.

Though he’s known for lighter stories, Riddler has also starred in more serious tales. In the one-shot Riddler: The Riddle Factory (1995) by Matt Wagner he hosts an underground game show to find dirt on celebrities. Many of the famous people he targets and humiliates apparently commit suicide, which suggests that he might have had something to do with their deaths.

The Riddler was a part of Jeph Loeb and Tim Sale’s Batman: The Long Halloween miniseries in 1996-1997. He gets hired by Carmine Falcone to discover the Holiday Killer’s identity, survives Holiday’s attack on Falcone’s office, and is sought by Batman for information on Harvey Dent.

In “Hush,” another Loeb story that appeared in Batman #608-619 (December 2002-November 2003), Riddler is diagnosed with cancer. He finds one of Ra’s al Ghul’s Lazarus Pits and uses it to heal himself, then connects with Dr. Thomas Elliot, who secretly becomes the masked criminal Hush. When Hush announces that he wants to get revenge on his childhood friend, Bruce Wayne, he and Riddler plot with other villains to destroy Batman.

Starting in Detective Comics #822 (2006), Riddler awakens from a year-long coma due to a head injury and is somehow cured of his obsession with riddles. He decides to take a break from the life of crime by opening a private detective agency, even partnering with Batman. In one case, they prove Bruce Wayne’s innocence when he is implicated in a crime.

As part of the DC Rebirth, he had a larger story, “War of Jokes and Riddles,” which began in Batman Vol. 3 #25 (August 2017) by Tom King and Mikel Janin. The war begins when Riddler offers a partnership to the Joker, based on the logic that neither would be satisfied if the other killed Batman. In reply, Joker shoots him in the stomach and leaves with Batman on his trail. After healing from the wound, Riddler creates a team with other Batman villains to attack Joker and his own crew of big name baddies. Throughout their war, they claim territory in Gotham, and Riddler convinces Batman to join his side in the conflict. During a fight between Batman, Joker, and Riddler, Batman nearly kills Riddler but is prevented from doing so by Joker who has achieved what he’d been missing throughout the conflict: the ability to laugh.

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