One of the darkest is 'The Killing Joke'. It delves deep into the relationship between Batman and the Joker. The Joker's attempt to prove that one bad day can drive anyone insane is both disturbing and thought - provoking.
The Joker is a prominent villain in many of the darkest Batman graphic novels. For example, in 'The Killing Joke', he is the central antagonist, with his maniacal plans and his complex relationship with Batman. His actions are often very dark and disturbing.
Definitely check out 'Batman: Year One'. It shows a darker side of Gotham City as Batman is just starting out. It's gritty and real, depicting his early struggles. And 'Batman: The Dark Knight Returns' is also a classic. It shows an older, more jaded Batman coming out of retirement in a world that has become even more corrupt and violent.
Sure. 'Dark Victory' is a great but dark one. It continues the story from 'The Long Halloween' and explores more of Gotham's underworld and Batman's battle against it. There are some really intense and dark moments in this one.
His relationship with other villains can change. After saving Batman, he might be shunned by his fellow villains, which could lead to him further exploring his new - found moral side. He could then form an uneasy alliance with Batman to fight against the other villains who now see him as a traitor.
The Joker is a likely suspect. He loves to target Batman's loved ones to mess with him. He might use the kidnapping as a way to draw Batman into a twisted game, setting up elaborate traps along the way.
I think 'The Long Halloween' is a top - notch Batman villain story. It's a mystery - thriller that has Batman trying to figure out who is committing murders on holidays. The story involves many of his classic villains like Two - Face, the Penguin, and the Riddler. It shows how they interact with each other and with Batman in a complex web of crime and deception.
One possibility could be that Batman, after facing one too many betrayals in Gotham, decides to take a different path. Maybe the constant struggle against crime with little real change in the city makes him cynical. He could start using his skills and resources to control the underworld instead of fighting it. For example, he might start dictating which criminals can operate and where, creating a new order that is still dark but under his command.