"Batman!? But how could he have figured out my nefarious schee-- oh, wait, that's right, I told him about it."
―The Riddler

Possibly the worst gimmick of all time. The Riddler's thing is... he rats himself out to the police. I know, right? He lives in Gotham City, and tries to defeat Batman... how? By telling Batman exactly where he's going to be committing a crime... and then committing a crime there. This invariably gets the crap kicked out of him, and dumps him right back in the asylum. Loser.

However after a long stint in the Asylum ( during which he watched all the Saw movies repeatedly) he came out with anew lease of life , putting people in bizarre death traps and trying to escape his overt campness and stereotypical homosexuality of his earlier years. He also developed a bizarre fetish for brain damaged monkeys. Don't ask what he does with them , i've seen it and still have problems keeping food down. I mean : if you're going to walk around in skintight lycra with a cane some serious signals are being sent. Loser.
Batman Meets the Riddler-0

Batman Meets the Riddler-0

One of Batman's first documented battles of wit with Riddler.