PepperSocks
Bluelight Crew
The Chili Cookoff is hands down my favorite episode.
It's in my top 5 for sure

BTW; I'm 22; started watching when I was 5. I'm all about classical Simpsons and I'm definitely not middle aged. As for the young-uns right now (5-16); I'm not sure what their view is on classic Simpsons.
My brother-in-law has tried to watch some good ones with his my 5 year old daughter but he thinks she's still too young to get it. I have to say though I didn't "get it" when I was that young; I just watched it; I seemed to like it without understanding it like I do now.