His stand-up was bad back then too

40 years ago in the UK it was shown at 8am as a filler program when nobody was watching, because it was so painfully contrived

Personally I don't have as much of an issue with when they're poking fun at him per se, but when they denegrate or damage things he has clearly worked hard on and put a lot of passion into, that's crossing a line for me. It becomes incredibly mean-spirited.

There are two examples in this compilation video. One at the linked time, and another at 6:33. Especially with how happy he is to see Leslie in the second clip until she destroys his art. It's honestly heart-breaking. The pie to the face that came a little bit before that was also hard to watch and really felt mean. Dunno if that's because of how cold and calculated it was (vs the more usual off-the-cuff comments), or because it was a physical act rather than verbal, or something else. But I didn't like it.

It feels cringe (to me) cause these type of people are often bullied in real life work places, again with no real reason.

It's the opposite of the Lil' Sebastian thing, where there's that horse that everyone idolizes for no discernible reason. Although with that, there's the one character who doesn't understand why they do that, so maybe that's what the Jerry thing needed? Or perhaps that would have made it even sadder lol.

It is kinda brilliant though, the way they set it up.

If you don’t like the joke, you can always fall back to the meta level: this is a 40-something dad recalling how dumb and cringe-worthy he and his friends were in their 20s.

The example I think that got me to dislike the trope was in Austin and Ally. The character Desmond was eating a muffin with the muffin wrapper on, and one of the characters mentioned you "have to remove the wrapper before eating it", so he removes the wrapper and throws the muffin away and starts eating the wrapper because that's how he interpreted their advice. And I'm thinking has there ever been a teenager who didn't have some instinct on how to eat a muffin.

Art imitates life

I never saw those moments as Kif being homophobic. I read it as a subordinate being repulsed by the idea of seeing his commanding officer naked.

I only remember one instance of Kif being homophobic, when Zapp says Lee Lemon is filling him with “other emotions that are weird and confusing.” Not wanting to constantly see your commanding officer naked isn’t homophobia.

And his annoyance when Zapp sang a name-swapped version of Lola was about how Zapp is acting toward Leela by doing that rather than the subject matter of the original song. Zapp even replaced the trans subject with a cis one, what could a transphobe even be objecting to?