Batman has the most twisted and obsessive villains in the DC Universe, even when compared to the other of the iconic Riddler pits himself against Batman in increasingly desperate attempts to prove his superiority, however it turns out the Gotham villain also loathes Olliver Queen's Green Arrow.
Green Arrow has his own host of criminals he's had to deal with in order to protect Star City, including the likes of Malcolm Merlyn, Brick, Onomatopoeia, Prometheus and Count Vertigo. Conversely, Batman's own iconic rogues gallery of villains often aim higher than domination of Gotham City alone. Some have gone farther in branching out - like Joker currently traveling America, causing chaos or Poison Ivy's ongoing mission to bring about a new extinction event. For most of Gotham's villains, setting out to battle Green Arrow would effectively be slumming it, and yet Riddler took on the Emerald Archer with gusto.
Beginning in Judd Winick and Phil Hester's Green Arrow #35, readers see Oliver Queen come up against the Riddler, who has hired to cause a bunch of harmless pranks across the city as a distraction for another villain. Oliver is able to capture Riddler, but he still doesn't know who hired him. With the entire city in danger, Green Arrow shows he's the scariest vigilante by torturing Riddler. In addition to dislocating both of Riddler's shoulders, Green Arrow also beats him until he gives up the information. While Riddler did eventually tell Oliver what he wanted, this event seemed to have a lasting impact on Riddler, since he returned to Star City soon after, but this time he wasn't there to tell riddles. He was there for revenge.
Riddler's Grudge Against Green Arrow Is Personal
When Riddler returned to Star City in Green Arrow #50, he hired the assassin Constantine Drakon to kidnap Roy Harper, all to lure Oliver into a trap. The important thing to note here is Riddler really didn't leave any riddles for Green Arrow, as is his trademark Upon returning after Green Arrow tortured him, Riddler was only here to hurt Oliver. Riddler proved he was equal to Joker in brutality when - after shooting Oliver in both shoulders - he proceeded to beat the hero with a baseball bat in a scene that mimicked the death of Jason Todd. Batman is brutal in his fight against crime, but Oliver has a history of causing grievous harm to his criminals, and it seems that was enough to leave Riddler obsessed with revenge rather than trying to prove his brilliance like normal.
Green Arrow Pushed Riddler Too Far
Green Arrow is often treated as a knock-off as Batman, operating as a crime-fighting millionaire, but he's actually even more low-tech, taking his violence further in order to retain an edge over his opponents. While Batman has inflicted terrible injuries in the past, the Dark Knight rigidly sticks to what he considers necessary to get the job done, and he actively denies his emotions while in costume. By pushing things further than Batman, Green Arrow created a far more personal rivalry with Riddler, discovering that when the villain is no longer trying to prove himself, he's even more dangerous. Strange as it is to believe, Green Arrow managed to push Riddler to the point where - as much as he considers Batman his main intellectual rival - he hates Bruce's Justice League ally in a far more visceral way.
