The Simpsonsboasts some of the most iconic characters in animation history, and they’re not all nice.
Sometimes it’s on purpose, sometimes by neglect.
Ranking them is merely a matter of degree, consistency, and the nature of their behavior.
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Waylon Smithers (Harry Shearer) serves his infamous boss as both an assistant and advisor.
Still, though, there are moments when there’s no trace of kindness to be found.
InThe Simpsons Movie, he shows that he’s willing to laugh at you until he’s physically incapable.
This is not the demeanor of an empathetic child, let alone a sympathetic one.
Extreme flammability aside, they’re often so visibly dangerous that only Krusty would give them a thumbs up.
On both a large and small scale, Krusty’s indifference is (hysterically) disgraceful.
This guy is a reminder that saying “dude” all the time doesn’t make you cool.
Ergo, he’s in charge of lots of murders.
His employees aren’t always successful, but the intent is there.
Fat Tony is so powerful that he has the gall to ask “What’s a truck?”
Toss ‘em a fish and watch ‘em slap their fins together."
Quimby’s demeaning remarks reflect his own approach towards power.
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Even the seal on his office wall reads “Corruptus in Extremis.”
It doesn’t take a linguistics major to figure that one out; this man needs to be stopped.
Ironically, Bob made it more educational and intellectually stimulating.
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Indeed, Sideshow Bob is a very sophisticated villain.
Burns
Simply put, the man who blocks out the sun is the most evil person in town.
That happens in the season six finale, in which every citizen of Springfield is tempted to shoot him.
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Even Smithers leaves his side (after barely talking his boss out of stealing candy from a baby).
He’s the worst guy in Springfield, hands down.
NEXT:The Best Sports Episodes of ‘The Simpsons,’ Ranked
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