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  • Adorkable:
    • His Gotham version is oddly endearing before he becomes a villain; he's a science-loving Nice Guy and a hopeless romantic who has stunted social skills, speaking too quickly and too formally at times, he has a macabre sense of humor, and he can't help but speak in riddles, much to the annoyance of others. There's even a scene where he uses a magnifying glass and forceps to pick onions out of his lunch. Even after becoming a murderous villain, he's still a gigantic nerd.
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    • His portrayal in TAS is also endearingly nerdy at times, such as in "Riddler's Reform" when a he finds himself at a genuine loss for words when beautiful women compliment him.
  • Cant Unhear It: Right now you're probably picturing him sounding like either John Glover or Wally Wingert — and most definitely Frank Gorshin.
  • Complete Monster:
    • Batman: Earth One Volume Two: This volume's Big Bad, The Riddler, is a nobody attempting to be somebody. To that end, after Mayor Cobblepot's death, he takes over one fifth of his criminal empire and has aspirations on the other 80 percent. Framing his assassinations as mass killings, the Riddler rigs an elevator with a bomb and gives the inhabitants sixty seconds to answer a riddle, killing all on board, including his target, when time is up. His next target is killed when he bombs an art museum. The third is onboard a public train with families and children aboard. When Batman gets the riddle correct, the Riddler blows up the train anyways and later attempts to blow up the police precinct to tie up loose ends.
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    • Batman: Doomsday Prophecy (Super Powers Which Way Books): The Riddler is more sinister than usual. Threatening to "end Batman", Riddler kidnaps Commissioner Gordon and attempts to use a Car Bomb to kill him and Batman. Later, Riddler lures Batman to Washington DC, where he kidnaps an actor dressed as Batman and threatens to drop him from a great height if Batman does not reveal his secret identity. But his worst act is luring Batman to a puppet show called The Riddle, held in a children's theater. Riddler sets the theater on fire, willing to let the children in the audience die, just to get the better of Batman.
    • The Batman, by David Voss: The Riddler, Edward Nashton, is a Serial Killer who prefers murdering a parent and their child, leaving behind riddles for the police to solve for his next murders. Having killed Black Mask's wife by chopping off her legs and hanging his son, Riddler would go on to kill Jason Todd's mother and brother by making them inject poison into themselves. Later forcing Batman to solve a riddle to prevent the mayor's husband and daughter from dying, Riddler still has the husband murdered despite Batman solving his riddle, having Batman framed for his death. Capturing Bruce Wayne and his ex-girlfriend Julie Madison, Riddler has Bruce and three other rich men fight to the death to decide who's really Batman, threatening to drown Madison should they all refuse.
  • Dork Age: Several examples.
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    • His metrosexual neck-Tattooed Crook period during Judd Winnick's Green Arrow in the 2000s.
    • While his appearances in Batman: The Animated Series are generally well-liked, some of his video-game based gimmick episodes are not.
    • Likewise, while his portrayal in The Batman was enjoyable, his Marilyn Manson look-alike costume-design is best forgotten.
    • While he has been generally well written in Snyder and King's runs, a lot of people (including Catwoman in universe) can't take his sideburns seriously.
  • Hilarious in Hindsight: He's well known for being an Insufferable Genius, frequently boasting about his intelligence to people around him and saying he's smarter than they are. When introduced in Power Rangers in Space, the Trope Namers for the Psycho Rangers introduce themselves by boasting they're better than the Rangers, with the Blue Psycho Ranger saying they're smarter. Thanks to certain casting in the Batman: Arkham Series, Psycho Blue Ranger and the Riddler now share a voice actor.
  • Magnificent Bastard: Batman: The Brave and the Bold: The Riddler, real name Edward Nygma, is a brilliant puzzlemaster with an affinity for puns and outwitting his opponents. When one of Riddler's heists is thwarted by the arrogant Batwoman, Riddler baits and unmasks the hero due to her smug personality, and, when Batwoman tries to get revenge on Riddler years later, he outwits her yet again, nearly killing her and taking down Batman in the same move before being stopped. Returning in Scooby-Doo! & Batman: The Brave and the Bold, Riddler masterminds a diabolical scheme to create a deadly teleportation device. Kidnapping the Question and disguising himself as the hero to gain intel on the investigation into his crimes, Riddler fools even Batman himself with the disguise, all while using Clayface to pull off a variety of successful heists while giving him information on Batman's past that throws the hero off his game. Riddler ultimately finishes up the teleporter and escapes capture when exposed, nearly pulling off his criminal scheme in its entirety with ease.
  • My Real Daddy: While Dick Sprang and Bill Finger created him, he only appeared twice before Frank Gorshin depicted him — and he created most of his memorable aspects, such as his dapper suit and his role as Batman's intellectual superior.
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