The Simpsons has been around for 30 years now, and as is natural in an episodic show such as this, there’s been a whole host of antagonists for the main characters to deal with. To try and keep plots fresh (without a crazy wedding or Marge becoming a robot), new characters are often introduced specifically as roadblocks for the family to deal with.
This in and of itself is nothing new though. The characters featured here span pre and post-Golden Era (commonly thought of as Seasons 3-4 until Seasons 9-10), though a good majority did appear during that sweet spot. For all the other criticisms you can throw at the show down the years, shortage of guest stars is definitely not one of them.
Importantly, this is villains in particular; and as such they need to have done something fitting the description of villainous to earn their spot. For example, while Nelson is a bully, he’s on Bart or Lisa’s side in quite a few episodes, so isn’t really in the ballpark of evilness.
Likewise, career criminal Snake has shot Apu, sure, but there’s just a $100 fine for that these days. The ones that make the cut are much more monstrous.
Stacey Henley is a published author, avid gamer and all-round nerd. She can most often be found roaming through vivid expansive spaces and discovering the world around her, but only in video games. In real life, she mostly stays home.