Ooooh! Zombie thread resurrection! Can I play?
My fave Simpsons moments almost always involve Comic Book Guy:
To Lisa:"Thats a very rare issue of Mary Worth, in which she advocates suicide"
To Bart: "I must get on the internet to register my disgust immediately"
Comic Book Guy dating Principal Skinners mother: priceless episode. After their breakup, he's inconsolable. Marge tells him they were just too different. He says "I don't understand". Marge ponders a moment, then tells him "You're Marvel, she's DC." He immediately replies "I understand completely".
Speaking of Skinner, the single biggest laugh I ever had from a Simpsons episode was when he walked into a scene dressed in Michele Pfeiffer's Catwoman costume from "Batman Returns", defiantly insisting he's NOT a sissy. OMG, laughed so hard tears were pouring down my face.
Anything with Sideshow Bob.
Anything where Homer or Lisa interact with the Apple store.
The entire ep when Homer accidentally moves to the gay part of town, esp when a twink skateboards past Homer and Smithers and shouts "hey, is that the hot bear we heard you've been dating?"
And of course Homer's legendary defeatist screed to his children: "Well, kids, you tried your best and failed miserably. The moral is, never try..."
The shows been circling the drain for well over a decade now, but when it hit the mark it was (and occasionally still is) pure genius.