Murder, mayhem, and general mischief regularly disrupt the lives of the Simpsons and the citizens of Springfield, thanks to a colorful cast of nogoodniks who bring chaos wherever they go. Ranging from petty crooks to would-be world dominators, these villains each add their own unique brand of trouble to the town that has seen its fair share of bedlam.

While some of these miscreants return time and again to seek revenge against Fox’s first family of animation, others appeared in just a single, memorable episode of The Simpsons, yet left a strong enough impression to create a lasting mark on pop culture.

Here is a look at the various villains to ever darken the doorstep of the Simpson family doorstep.