In regards to “The War of Jokes and Riddles” and how dark it is, the Joker is very pointedly set up by King to be in a situation where he’s “lost his smile.” He’s in a funk, and he’s targeted the Riddler as the reason why. This is a Riddler, I think, that King imagines after the events of “Zero Year,” so it’s a Riddler who literally took a whole city hostage. For a year. That’s hardly a one-note riddle guy.
I get that readers want to escape in these comics, but the logic of the storytelling is solid. What happens when there are two supervillains running around whose gimmick is to screw around with people? What does it look like when they realize the other one exists? It’s not pretty. They literally don’t care what happens to ordinary people. I like (the first part, anyway, because I haven’t seen the second yet) the Kite Man origin. As someone pointed out, that’s what happens when you try to play both sides and you get caught. The guy lost his kid, and went insane. This is literally the most relevant Kite Man has ever been. In King’s imagination, I would expect something similar to have happened to the guy who became the Joker, something so unspeakably awful that he had a complete break with reality.
I’m not a fan of Killing Joke. I think Moore crosses a line that should not be crossed, and I think it’s a tragedy that DC actually kept Crippled Barbara in continuity for decades just because Moore was a prestigious and popular writer. The idea of it is abhorrent. If it had been a character who made their first appearance in it and meant nothing except a message sent to Commissioner Gordon, it would be one thing. At least in Watchmen Moore did something similar as part of that character’s own story.
It’s about perspective. King has one of the most comprehensive perspectives I’ve ever seen in comics. To my mind, it’s comparable to Mark Waid unlocking Flash mythology, figuring out Wally West and then positioning the rest of the speedsters around him. James Robinson gets all the credit for Starman, but I always thought Waid did it better. Robinson sort of cheated by creating a new character. When Waid created someone new (Max Mercury, Impulse), it was someone who contributed to the tapestry rather than defined it. King has done that with Gotham Girl. I imagine when he gets back to her this’ll be more apparent.