9. The Death of the Joker - Batman Beyond
Whenever you talk about the twisted side of comic books, things always seem to tie back to the Joker. No matter what form you find him in, the Clown Prince of Crime has inspired many great lines and a whole bunch of uneasiness from everyone that sees him. Though he may have met his end in many different transformations of the Batman saga, the most unsettling final moments from the Joker actually came from the animated series.
Set in 2039, Batman Beyond picks up where the original animated series left off, but never fully answered the question of where Batman's original foes went.
In the animated movie Return of the Joker, we flashback to when the Joker kidnapped Robin and brainwashed him into being a mini version of himself. It already sounds messed up, but once you see young Tim Drake's face as the Joker, that demented smile is enough to make anyone's blood curdle.
In an attempt to finally kill off the Caped Crusader, Joker enlists young Drake to kill his former mentor, only to have him come to senses just enough to direct the lethal gunshot towards the sinister clown. Mark Hamill would end up playing the Joker several more times in the DCAU, but with just a few short gasps, the first brilliant iteration of the classic character came to a bone chilling end.