Top 100 Batman VILLAINS

1 - The Riddler

#1 - Riddler
First Appearance: Detective Comics #140 (Dec 1948)

"For the record? It's killing me not to ask you "why is this man smiling?"" ~Riddler

Earned bravado. Extreme intelligence. Amusingly clever arrogance. Megalomania incarnate.

The Riddler.

The Riddler is my third favorite villain. Period. What makes him so close to utter perfection is that mind. That perfectly crafted mind that constantly provides and provides and provides. Every Riddler action is clever or humorous and always d***ish, while every line of dialogue is full of that same snarkishly jerkwit that makes Riddler a joy to root both for and against. His criminal plans always force writers to really work their own creative intellects to come up with new and ingenious methods of planning as well as the creation of unique and hard-to-solve riddles that readers work just as hard to figure out as the Bat. And that's the perfect sign of a villain that draws you right into the story; you're as eager to solve the mystery as Batman is.

Riddler is also one of the few villains to win. And that's a phrase I really don't use loosely. Perhaps my all-time favorite Riddler moment is the ending of the Hush storyline, where... well, let's just say that the Riddler wins. He so perfectly plays every single character involved from hero to villain to supporting cast member - hell even the folks in Metropolis - that he ends up getting exactly what he wants.

More awesome than that is his time spent as a detective, where Riddler gleefully works as a good guy and ends up being even more of a thorn in Batman's side by simply doing Batman's job better than him. I mean, that is the ultimate in epic trolling, and one of the stories that resulted in me becoming HUGELY into the Riddler's character. He of course is one of the few men that has deduced Bruce Wayne's nighttime hobby, and at one point (after being hired by Nightwing), deduces that Dick Grayson is Nightwing. So, solid work there, too.

Frankly, every facet of the Riddler just comes off as cool to me. He's a psychotic who knows he's a bit psychotic, but uses his weakness to play to his strengths. He can troll with the best, and also pull of legit crimes with astounding intelligence that makes most masterminds look like dullards. He's the perfect package of supervillain perfection, and for that he earns spot #1 on my all-time Batman villain list.

Greatest Riddler Stories Ever Told (That Aren't Hush):
1. The 1966 Batman TV Series - Frank Gorshin kills it as the Riddler in the old West TV show, and he easily steals the spot as the best character on the series. Constantly watchable, full of personality and also some of the most ingenious plans on the show (which admittedly aren't that grand, but for the show they were), Riddler rocks it.

2. Arkham Asylum/City/Origins - When you think about it, Riddler really plays a bigger role than even the Joker in this video game series, as his constant dialogue throughout each game really builds his character and relationship with Batman. A little meta, full of hilarious hubris and sinister hatred for the Bat, the AA titles have really cemented the Riddler as my favorite personality in the Batman mythos.

3. Dark Knight, Dark City - The story that provided Grant Morrison his inspiration for Simon Hurt, Riddler just rocks it in this tale about the meaning of Gotham City. Amazing artwork (Mike Mignola!) and amazing writing (Peter Milligan!) cements this as not just a great Riddler story but one of the Bat's best as well.