The Riddler
3 minutes...and go...
Why did the Riddler try to get Batman to engage him with riddles? Why, of all the super-villains, did he try to use logic puzzles? It always seemed to me that villains were more compelling with they had real plans. Real villainy. Real devious messages.
The Riddler? I think he just wanted love. I mean, his whole backstory is centered around being the nerd, being scored, being irate, being rejected.
And then he turned that anger, that scorn, on Batman. But not to kill him. Sure, the Riddler had lethal traps and cruel puzzles from time to time. And he certainly would have (and did) commit murder, depending on the version. But I think all Riddler secretly wanted was engagement.
I mean, the Riddler seeks out the only other person in Gotham who would certainly understand lonliness. The one person who is out every night, without fail, trying to find connection.
Of course the Riddler would focus on Batman.
Of course the Riddler would look for love in a person who would scorn him.
The Riddler wasn't trying to get diamonds. Or money from Gotham's vault. Or, hell, I don't think the Riddler even wanted the girlfriend who turned him down.
The Riddler wanted attention.
Like a child who will take the negetive attention when he can't get the good.
So the Riddler gave Batman riddles. Because in his childish mind, an angry father-figure just might appreciate his macaroni drawings. Or the bombs he planted on the bridge. And he knew Batman would always be there. To play his game. No matter how tired Batman was from work. He would never scorn poor Riddler. He would play, he would answer the riddles, and he would pat Riddler on the head and tell him "Good one."
...And then lock his ass up.
Do you think Riddler got Covid19 in Arkham Asylum?