The Most Evil Simpsons Characters, Ranked

Sideshow Bob

Despite being repeatedly sentenced and imprisoned, Bob continuously escapes to wreak havoc. His nemesis, Bart, has been targeted for various crimes, including attempted murder.

Kang and Kodos

These aliens feature in "Treehouse of Horror" episodes, often attempting to invade Earth. Their sinister plans include posing as political figures and enjoying watching the chaos unfold from afar, such as during a zombie apocalypse.

Fat Tony

The original head of the Springfield mafia, Fat Tony sees crime as a business motivated by money rather than personal vendettas.

Mr. Burns

Personifying the negative aspects of wealth, Mr. Burns is depicted as cold, calculating, and greedy. He lacks empathy for his employees and readily dismisses them, regardless of their loyalty or contributions.

Artie Ziff

Before Homer, Marge's only love interest was Artie Ziff, her creepy prom date known for his "busy hands." Despite his wealth and success, Artie's life lacks meaning without Marge, leading him to dedicate himself to stalking her.

Lyle Lanley

In "Marge vs. the Monorail," Springfield gets a windfall and decides to invest in a questionable monorail system.

Thai Ridgeback

In "The Simpsons Movie," Russ Cargill stands out as a memorable antagonist. Unlike other villains on the show, Cargill isn't a typical megalomaniac but rather a wealthy environmentalist put in charge of the Environmental Protection Agency.


In "Homer the Vigilante," guest star Sam Neill portrays Molloy, the infamous "Springfield Cat Burglar." Homer organizes a neighborhood watch to catch Molloy, and against the odds, succeeds with the help of his father, putting the elusive crook behind bars.