I graduated high school and started college in 2000, so for me there was a very clear demarcation, but I suppose you're right now that I think about it.
Maxaroni is literal Poochie from Itchy and Scratchy, except he's not a dog.
The principle with the bow tie was actually a roadie for Big Brother and the Holding Company. Don't get him him high, he'll talk your ear off about the time he fucked Janice Joplin.