Take a look at the 1st transformation of The Riddler. Hes not some agent nor some geek. He is as stated a
Dangerous Tricky Criminal. Hes also seemingly wealthy judging by his pad (Most likely from all of the money hes stolen) as well as a sharp dresser. The Riddler is more than just mere question marks as you can clearly see.
http://www.youtube.com/watch?v=inFV1irkvdk
If you want to get deeper into the darker layers of his psyche, check out this video and see his fascination with torture! Weak? Check out more of Gorshins portrayals and see that The Riddler has landed some punches, but he and everyone else was beaten up in that show.

He also had some nice disguises. Make no mistake, when the giggles stopped, The Riddler was entirely creepy. Of course he really didnt need the mask because everyone knew who he was and he didnt mind. Maybe it has a more disturbing meaning, but you can never tell. Though it was a TV show, you can still get an idea of what he does to his victims, and he has plenty of them.
Im sure that most of us can agree that this is the best portrayal of The Riddler. Suave, highly intelligent, multi lingual, witty, and indeed creepy. In this version as well as Gorshins, The Riddler has got the best of Batman and lured him into a trap, leaving him to die. What gets him caught is that The Riddler spends too much time trying to perfect the trap and misses minor things in which Batman figures out and escapes. The Riddler did not need to say Riddle me this to tell you his next riddle, you either got it or you didnt. Though all of his riddles werent that simple, some of them had double meanings so that you were either going the right way or the wrong way. Not every riddle has to make perfect sense, you just have to think like The Riddler, which obviously isnt easy. In addition, his tapes from B:AA gives you more of an idea of how he is. His bursts of anger and his intimidation.
Who better to give you an idea of The Riddlers psychology than the great Hannibal Lecter. You dont believe me? You should check out the trailer for Silence of the Lambs and see how hes described. Blue unblinking eyes the haunt you, just like Frank Gorshin. Never mind his eating habits. Just like The Riddler he is suave, sophisticated, dangerous, and creepy. He uses riddles, anagrams and cryptic messages as well.
What messed up The Riddlers character to a certain point was, without a doubt, was Batman Forever. Though he was still dangerous and strange, he was made a weakling, which bled into the comic world. An element that I did notice was how perverted The Riddler was in BF as he was in the 60s TV series. This places me in the mind of this man
Ted Bundy. You guessed it, suave, sophisticated, dangerous, and creepy (and perverted). He had many disguises as well. He taught himself psychology to trick people into doing what he wanted. Also had outbursts of anger. Look at his smirk, seems familiar right?
There is no need to give The Riddler an origin of something that he never was, because he is perfectly insane, weird and dangerous as he has been. The elements have always been there, but some of you just didnt see it. Yet, The Riddler is in fact an enigma and in himself a riddle, so how could you easily solve that without thinking as he thinks?
P.S. I thought this page could use some pictures

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