- Cant Un Hear 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.
- 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.
- Dork Age: Several examples.
- 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.
- 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.
YMMV / The Riddler