The Joker
The Joker has done some god awful things to the Dark Knight and to people in general. His biggest crime against Batman was an underhanded one which affected Batman through the series. After Dick Grayson left Batman to become Nightwing, Batman took under his wing a new orphan, Jason Todd. The Joker single-handedly manipulated Todd to the brink of breakdown and killed him while he made The Dark Knight fail to save him. An act which haunted him and became the single biggest regret of his life.
The Riddler
The Riddler is one criminal that the Dark Knight underestimated. The villain teamed up with Bruce Wayne’s childhood friend Tommy Eliot to lead the hero on a wild goose chase where certain events happened that seemed to threaten Batman’s secret identity. It was later revealed that The Riddler was the one behind everything that happened in the Hush events. The mind games make B-man so paranoid that he suffered the aftermath even in other stories like War Games and Under the Red Hood.
Talia al Ghul
What would a list be without the psycho ex-girlfriend Talia al Ghul? Talia, through the years, has proved herself to have a complicated relationship with Bruce Wayne. A polarizing force laid out in a gray area, Talia was once loved by Bruce. Then she went through a bit of a paranoia when she discovered that Bruce preferred to do his job than devote 100% of his time with her.So what does she do? Roofied his drink, basically raping him and carry his child. She then tells him that she suffered a miscarriage only to discover ten years later that she didn’t.
