Dark Moments in Media

What are some dark moments from your favorite cartoon, TV show, comic, book, movie, video game, etc. that you have encountered?

For me in comics I would say Alan Moore's story of Vigilante(I believe it was 16-17 Happy Father's Day or just Father's Day). In cartoons the Simpson's episode Homer's enemy. In Video Games a lot of the things in Majora's Mask stick out, but personally I believe the final day scene when you visit Cremia and Romani is dark. In books pretty much everything from Greek Mythology.

Spider-man: Reign, the entire story.

Darkest cover I can think of, seriously this one got to me as a kid.

@DoomDoomDoom: That got to me just now. Geez.

From comics, this moment. It just accentuated how bad the series was: I'll add more later.

Those were dark days

Samurai Jack episode 3. I can't find a video of the scene I'm talking about but, after he basically destroys the majority of these robotic bug creatures they start to back of and Jack just doesn't let them, he proceeds to destroy every last one.

Maybe not the darkest moment now but as a kid, to me, the idea that the hero figure didn't let the beaten villains run away and escape but choose to kill them all was very dark.

Crossed. All of it.... FML.

In TV I was shocked when Zim harvested all those human brains in Invader Zim. Bloody Gir also surprised me.

"WHY'S HIS HEAD SO BIG? WHY ISSSS HIS HEAD SO BIG?"