I still enjoyed seasons past the tenth, and I say anything close to the 300th or past the 14th season where the animation changes to digital and sound and music gags are off their mark is where things really dip.I have the first 3 seasons of the Simpsons on DVD. At what season should I stop purchasing sets? I was told that season 8 was the last consistently good season. I haven't watched Simpsons since the late 1990's, but I checked out some recent episodes on Hulu and they were bad. What the hell happened? Did they run out of ideas, or was it a change in the philosophy of the writers. I don't remember them ever resorting to sight gags and slapstick for the sake of slapstick.
The writing team on the first few seasons were so subverse. It was like they were starving artists who were hungry to prove something.
And then I found these seasons leading up to the HD seasons to still be charming. The animation and sound/musical cues (or lack of) becomes a hindrance now to jokes though.
But then the HD seasons become a total chore to watch for awhile thanks to even more sterile animation, going-through-the-motions voice acting (could Skinner and Flanders be even less funny now?), and writing that relies on too many pop culture trends now. What annoys me even more now though is that instead of using a rotation of Springfield residents, they keep using one-off stock generic characters to fill the backgrounds and say jokes. These past two seasons do have their uptick episodes though.