10. The Riddler Tries To Murder Children And Summon The Devil - Batman: Dark Knight, Dark City
Chances are, when confronted with the name 'The Riddler', you immediately think of a weedy guy in an admittedly sweet question mark suit getting the stuffing kicked out of him by someone for being a big nerd. And, to be fair, you'd generally be right... unless you were talking about the Riddler in Dark Nights, Dark City.
Because this series does what a million attempts of giving the Riddler mohawks and making him ripped could never do: it makes him legitimately menacing. Edward Nygma is, in this series, trying to summon a demon seemingly just for kicks, resulting in a plan that seems comprised specifically to traumatise the Dark Knight.
During the course of the comic, the Riddler hands Batman a baby doll that explodes into a bunch of human blood, leaves a hanging man for him to rescue, and then dressed a bunch of his henchmen up like zombies just to convince the Bat that he's already accomplished his evil plan.
In short, it looks like a particularly rough day at work for the Dark Knight, which is not even taking into account the fact that at every point of his hunt for the Riddler, the villain leaves him a baby to rescue from an awful situation.