"The Computer Wore Menace Shoes" has a number of my favorite dark moments.
Homer: Here it is everybody! The world's greatest web site!
[a highly annoying newbie web page, complete with several clashing sounds, is seen]
You'd think all the noises would be annoying, but they're not.
Bart: I got suspended from school today.
Homer: No kidding. [obviously ignoring and then continuing to ignore Bart] What do you think of my page, Lisa? Be honest, it's great, isn't it? Go ahead, say it's great if you want to.
Bart: They found a switchblade in my locker.
Lisa: Well, a web page is supposed to be a personal thing. You've just stolen copyrighted material from everyone else. They could sue you for that.
Bart: I took a swing at a cop.
Homer: They can't sue me if they don't know who I am. I'll just
call myself Mr. "X".
Bart: I'm just mad all the time.
Homer: Yep, you just can't go wrong with Mr. "X".
Woman: We'd like to award this years Pulitzer prize to Mr. "X". Unfortunately, we don't know who he is, so his cash award will be used to feed starving children.
Homer: Noooo! [runs down to podium]
Homer: I'm Mr. "X"! Gimme, gimme!
% Back at home.
Marge: I'm proud that you won the Pulitzer ...
Homer: Finally..
Marge: ... but I do feed bad about the starving children.
Homer: They're with God now.
Marge: Oh, well, that's good. [realizes] Hmmmm.
Moe keeping Moleman underneath his floor.
Flanders: [reading a computer screen] They're controlling our minds with flu shots. I knew it. Well, kids, now aren't you glad that we don't believe in inoculations?
Rod + Todd: [shivering from an apparent fever] Yay.
Todd: Mommy?