“Wait a second, is that a bong? . . . You have asthma? . . . Alright, move along.” – Principal Dondelinger

The care that The Simpsons put into every episode remains impressive all these years later.  Take Principal Dondelinger, a bit part created to act as the unwitting matchmaker for Homer and Marge back at Springfield High School in the 1970s.  Early in the episode, he catches Homer and Barney smoking regular cigarettes in the bathroom.  In response, he gives them detention and calls them “Springfield’s answer to Cheech and Chong”.  Later in the episode, he confronts a nameless student who, probably less than clearheaded, has tried to cram a bong inside his prom jacket.  Not only does Dondelinger mispronounce “bong”, but he lets the kid go, assuming it’s an inhaler.  In other words, Dondelinger is so clueless about weed that he doesn’t know what Cheech and Chong are smoking and fails to recognize actual marijuana when he sees it. 

It’s the little touches like those that allow an otherwise one-dimensional character to have some personality, stick in your mind, and get in some jokes that are both excellent and subtle.  He’s more than just another guy who doesn’t like Homer, he’s as fleshed out a 1970s principal as about six lines of dialogue allow.