There's pleeeenty of moments in later seasons (even a few in the classic ones) that will qualify as moments that don't work. I'll comment on those myself later, but for now, let me start with two examples where I think the mean approach was for the better.
Gonna come out and say it: Homer's Enemy is a freaking masterpiece of dark comedy. The episode goes out of its way to make Frank Grimes' life a complete misery from beginning to end, rewarding Homer's idiocy and driving poor Grimey (as he liked to be called) to literal self-destruction. But it's not being mean just for the sake of it, it's a brilliant deconstruction of what life at Springfield would truly be like, what consequences would arise from actually co-existing with Homer Simpson, or worse, trying to mimic him. It's simultaneously one of the most brutal and hilarious half hours I've seen. Pure genius.
Now for a more recent one. Remember that contest where the winner would have their original character featured in the show? Said winner was Peggy Black, a lady who came up with the character Ricardo Bomba. In the woman's own words, he was to be "someone that all the women love and all the men want to be". Al Jean described the gesture as "a thank you to loyal fans" and teased making the character a regular. They sent Peggy to work with the animators, and she couldn't be more excited.
The episode airs. Ricardo Bomba appears driving by a mountain side, and not ten seconds pass before he crashes his car into a cliff wall, causing it to explode. Just as he was about to finish his would-be catchphrase, too. That's it. Episode proceeds as normal. More than six years later, that's the first and last that was ever seen of Ricardo Bomba.
That's...that's really freaking mean to the lady who won the contest, after hyping up Bomba's introduction to the skies and making such a big deal out of it. By the exact same token, it was also hysterical. Easily my biggest laugh of an otherwise forgettable episode, hell, that whole season. I mean, you could argue Peggy was in on the joke from the beginning and was told to keep quiet not to ruin it, but I've yet to find any indication at all that this was the case. Closest thing to follow-up news in her reaction I've found lie on the comments of this article (which includes a clip that covers all of Bomba's screentime). Says this anonymous person:
Good one, Al Jean. Good one, you masterful dickhead.
Bring up moments of your own, fellow gaffers!
Gonna come out and say it: Homer's Enemy is a freaking masterpiece of dark comedy. The episode goes out of its way to make Frank Grimes' life a complete misery from beginning to end, rewarding Homer's idiocy and driving poor Grimey (as he liked to be called) to literal self-destruction. But it's not being mean just for the sake of it, it's a brilliant deconstruction of what life at Springfield would truly be like, what consequences would arise from actually co-existing with Homer Simpson, or worse, trying to mimic him. It's simultaneously one of the most brutal and hilarious half hours I've seen. Pure genius.
Now for a more recent one. Remember that contest where the winner would have their original character featured in the show? Said winner was Peggy Black, a lady who came up with the character Ricardo Bomba. In the woman's own words, he was to be "someone that all the women love and all the men want to be". Al Jean described the gesture as "a thank you to loyal fans" and teased making the character a regular. They sent Peggy to work with the animators, and she couldn't be more excited.
The episode airs. Ricardo Bomba appears driving by a mountain side, and not ten seconds pass before he crashes his car into a cliff wall, causing it to explode. Just as he was about to finish his would-be catchphrase, too. That's it. Episode proceeds as normal. More than six years later, that's the first and last that was ever seen of Ricardo Bomba.
That's...that's really freaking mean to the lady who won the contest, after hyping up Bomba's introduction to the skies and making such a big deal out of it. By the exact same token, it was also hysterical. Easily my biggest laugh of an otherwise forgettable episode, hell, that whole season. I mean, you could argue Peggy was in on the joke from the beginning and was told to keep quiet not to ruin it, but I've yet to find any indication at all that this was the case. Closest thing to follow-up news in her reaction I've found lie on the comments of this article (which includes a clip that covers all of Bomba's screentime). Says this anonymous person:
Good one, Al Jean. Good one, you masterful dickhead.
Bring up moments of your own, fellow gaffers!
