0110 - Herman Hermann (Patreon)
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I always got the impression that Herman was based on an actual person from a writer's childhood or something. He's very specific, and has the sort of odd creepy energy that might linger in someone's memory for years.
After a couple of significant early appearances, Herman quickly becomes the criminal who does things too serious for Snake, for example mimicking the Maynard from Pulp Fiction role in "22 Short Films About Springfield". Encouraging a 10 year old to start an army...that's weird, right? Herman's a creep.
Early on I think the intended running joke was that Herman would give several different reason for his arm loss, but as he falls into obscurity, so does this bit. In season 24's "To Cur, With Love", it is revealed the arm was removed by a passing van, in a flashback.
When this happens, Herman decides to open a gun shop...instead of go to piano school? That's not conjecture, it's he says, it's odd. By the time we get to season 24, our deep dives are going to be weird, I think.
This post is part of my "Every Simpsons Character Ever" series. For a list of my rules in this project, click here.