The Prince of Puzzles
Hi Diddle Riddle/Smack in the Middle
- "Question: What does no man want to have, yet no man wants to lose?"
"Answer: A lawsuit."
- ―The Riddler[src]
The Riddler is an infamous Gotham City criminal and one of Batman's greatest foes. He is a masked man in a bright green spandex costume that commits various bizarre crimes and leaves riddles leading to his next crime.
Riddler is a cackling, clue-dropping criminal. He delights in challenging Batman and Robin with his puzzles that he leaves at every scene of a crime. Although he was a high school dropout, Riddler is still highly intelligent and is able to leave riddles difficult to even the Caped Crusaders, which are often many-layered and contain several possible solutions. Riddler was the main villain of the first episode. He was also the main villain of the first comic, Riddler's Ruse.
- United Underworld and the Legion of Doom
- The Molehill Mob - Hired thugs for Riddler during his plot to steal the Moldavian postage stamps.
- Harry (portrayed by Allen Jaffe) - Member of The Molehill Mob.
- Molly (portrayed by Jill St. John) - Riddler's first moll.
- The River Rat Gang - Comprised of Whitey (portrayed by Roy Jenson), Whiskers (portrayed by Tim Herbert), and Fangs (portrayed by Marc Cavell). They assisted Riddler in a plot to dispose of King Boris. They all love cheese.
- Mousey (portrayed by Susan Silo) - Riddler's moll in the River Rat Gang. It is revealed that she dropped out of high school.
- Tallow and Matches (portrayed by Joe E. Tata and Michael Greene) - Simple henchmen who assisted Riddler in a plot to steal Incan Jewels that will be destroyed if exposed to oxygen.
- Moth (portrayed by Linda Gaye Scott) - His female partner during his plan to steal the Great Treasure of The Incas.
- C.B., Von Bloheim, Wolf (portrayed by Richard Bakalyan, Theodore Marcuse, and Burt Brandon) - Simple henchmen helping Riddler with his movie and help him with his plot to steal Mr. Van Jones's valuable collection of silent films.
- Pauline (portrayed by Sherry Jackson) - Riddler's moll during his movie and his plot, but when she was spotted by Batman she tried to escape but Batman caught her.
- Mr. Van Jones (portrayed by Francis X. Bushman) - collector of valuable silent films that Riddler wanted to steal.
- Across and Down (portrayed by Jim Lefebvre and Ken Scott) - Simple henchmen who helped Riddler get Professor Charm's Demolecularizer.
- Siren (portrayed by Joan Collins) She worked with Riddler.
- Betsy Boldface (portrayed by Peggy Ann Garner) Riddler assistant.
- Kayo and Cauliflower (portrayed by Nicholas Georgiade and Gil Perkins) Riddler thugs.