Growing up in the late 90s to early 2000s, my exposure to The Simpsons was when a majority of people were in agreement that the show was in decline due to the more outlandish nature of the gags and plots seeping it's way into the regular episodes (not just the Treehouse of Horror or non-canon ones). As such, I kinda associate the television series to an extent with these more 'wacky' episodes, even though I understand this is what began to turn people away from the series as a whole.

The first three seasons definitely feel a bit more grounded in reality and have a much more down to earth feel, but even that was starting to erode by then. An episode where Homer tries to find new purpose in life after being fired from his Power Plant job is fairly different in tone and feel than something like Bart accidentally getting roped up with the mob and believing the principal of his school was murdered. I think the reason why these more outlandish plots worked is because they just tip-toed on the boundaries of what 'worked' and what didn't. Characterization in Seasons 3-9 still felt pretty consistent and relatable, and worked great at satirizing issues in America. Homer fishing a British individual out of sugar is pretty silly, but isn't the driving force behind the plots themselves. It all works without turning the characters into broad stereotypes that exist for cheap laughs. Each Season up until 9 got a bit wackier with it's jokes which can definitely be offputting, but for me, I think it was Simpsons at it's peak. A good balance between being absurd and taking advantage of it's animated format, and using it to satirize society as a whole.

I think TheRealJims' video on 'The Computer Wore Menace Shoes' kinda illustrates where the series was going and puts my thoughts into post-Season 9 pretty well. It's still decently fun and creative even if these weird outlandish plots and gags became the main focus, but it's a fairly different show from what people would consider 'the golden years'.

So, eh. I like a lot of the stuff post-Season 4 and still consider it a decent time, with stuff between 4-9 being 'peak Simpsons' to me. Even something like Season 10-15 can be pretty funny going in with the mindset that it was more of a cartoon than anything else. I consider The Simpsons Movie (or Hit & Run) a good 'finale' to the entire series. I feel there was an earnest attempt to steer the series back into something more grounded when they switched to higher definition, but the series length kinda unfortunately made things a bit more stale. The more strict runtime the writers have received certainly doesn't help matters.

Super Eyepatch Wolf's retrospective on the series is also a fun watch if you haven't looked at it yet!