I forgot about this lol
OK...bridge to understanding Riddler.
To start. There's more to him than just gaining knowledge and proving how smart he is...that's not his goal. It's about, as Charlie Sheen would put it, WINNING. Riddler NEEDS to win, and this is only done by being better and smarter than his opponent.
In his childhood, he was FORCED to be better and smarter by his father. Edward was scared to death of losing, as he would receive both physical and mental abuse at the hands of his father. The mere thought scared him so much, he would obsess over improving himself, crafting his skill and intellect over virtually every subject, to prepare for any challenge that was thrown at him.
But when push came to shove...he wasn't as good as he thought. So he resorted to cheating, to deceive his father...to gain the much needed recognition and respect he he craved...and to spare him the pain of losing.
So what would this do to a kid? He was treat and crafted in the world of adulthood at a young age, by his pushy father. The traits that he learned as a CHILD affected him in his adulthood.
It's why when we're first introduced to him in the comics, he's already a criminal. Someone like him could never hold down a proper job, or proper relationships.
His egotism was born out of cheating. His mind was twisted out of cheating. His constant cheating, born out of the desire to constantly win. To prove his worth to his father.
Cheating to Edward would seem almost like a crime...and criminals, in order to cope, add coal to the fire, to stop the train from stopping.
Then the joy of winning, the feeling of being better than his father would have ever thought, the false notion that he won all did through his own 'amazing self', propelled him into a life of crime. So at some point in his career, Edward actually became unaware he cheated at all. He committed crimes that didn't force him to cheat to win, never pushing himself...that was until he gained confidence and became the Riddler.
Why Riddles? Is it because they are all that challenging to figure out...not really. I believe he uses riddles because, while they are a challenge, they are his downfall in the long run. A part of him believes no one will crack them...while at the same time, he hopes they do. Because he himself wants to be solved.
They act as clues...they always serve for his capture. I feel this is because he wants to be punished when caught out...He wants to be punished for deceiving his father...not being as brilliant as he made out...to receive the mental pain of reliving his fathers abuse for being a loser...all this ties into his obsessions.
He does it to win, while another part of him seems to do it to lose. He strives to win...but while subconsciously, begs to lose, despite the cheating he does, despite the praise he gives himself.
I feel sorry for him to be honest. Because deep down, he knows he will never win, he's not that good and he knows he deserves it