1. Ned Flanders 

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The words "Ned Flanders" and "Dark" don't seem like they mix, but beneath his sunny exterior lies a whole mess of disturbing shit. In the episode "Hurricane Neddy" we learn that Ned was once a troubled child whose beatnik parents essentially subjected him to a year long beating that forced him to suppress all of his negative impulses, and instead replace them with all those "Diddleys" and "Doodleys" everyone knows him for. Though he vows at the end of the episode to express his rage like a healthy person, it's pretty clear that he reverts back to being one big ticking time bomb of repression.

Key Line: "...And if you really tick me off, I'm gonna run you down with my car." 

2. Ms. Hoover 

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Ms. Hoover is an alcoholic who shows very clear signs of depression which is not ideal given that she's responsible for a classroom full of second graders. Clearly, it's taken a toll on her teaching abilities..

Key Line: "Since we have fifteen minutes until recess, please put down your pencils and stare at the front of the room."


3. Nelson Muntz

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As the school bully, Nelson is frequently painted as a villain, but when you actually stop to think about the fact that he's a ten year old boy whose dad walked out on him, and who has obvious issues at home, his anger issues suddenly start to make a lot more sense.

Key Line:  "I'm going away for a week. Cya!" (His mother does not seem to care if he disappears for long stretches of time.)

4. Laurleen Lumpkin 

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Laurleen's tenure on The Simpsons was brief but soul crushing. She begins her arc as a struggling cocktail waitress who tries to seduce Homer (with a downright beautiful song) because he's the only man that's ever treated her with an ounce of respect. Homer eventually rejects her advances, and she apparently takes it pretty hard because the next time we see her, she's clearly drunk and her voice actress has switched from Beverly D'Angelo, to the woman who does Lunchlady Dorris. (Note: Apparently she comes back in Season 19 but i'm not gonna talk about that because, well, fuck that...)

Key Line: "I spent last night in a ditch." 


5. Agnes Skinner

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Mrs. Skinner is painted as the quintessential overbearing mother, but I would argue that the opposite is true. There's a lot wrong with the episode "The Principal and the Pauper", in which it turns out Principal Skinner is actually an impostor named Armin Tanzarian, but I would argue that the worst part of it is the old woman's willingness cut her biological son out of her life forever (by tying him to a train no less) in favor of the man that stole his identity.

Key Line: "I'm sorry, Seymour.  It's nice you're alive, but you're just not what I'm
looking for in a son.  I'm glad you understand." 

6. Chief Wiggum

Hilarious Simpsons Characters That Are ACTUALLY Very Sad

Though he seems like he's just a big, incompetent teddy bear, Chief Wiggum is actually a very bad man. Whether it's putting a boot Ms. Hoover's car to get his son a part in the school play, or confiscating a ring toss game because Homer doesn't bribe him, the sheer number of times he out and out exploits his power as police chief is disturbing. Springfield is basically a police state.

Key Line: "The man i'm really looking for, wink, is a Mr. Bribe, wink, wink." 

 

7. Moe Szyslack

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It's no secret that Moe is a dark character, but just calling him a hateful, rage-filled, scumbag doesn't do justice to just how disturbed the character is. What people often overlook is the fact that after overreacting to crank calls and saying "Whaaaat?" a lot, Moe's most notable running gag is probably his repeated suicide attempts which...yeah, it's really messed up. There's not much more to say than that.

Key Line: "Hey 'pu, you got a breakfast cereal for people with Syphilis?" 

8. Mayor Quimby

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It's no surprise that The Simpsons would feature a satirically negative depiction of a politician, but Mayor Quimby's long history of embezzlement, adultery, and, yes, even murder, somehow manage to defy expectations.

Key Line: "I'll admit I used the city treasury to fund the murder of my enemies, but as Gabbo would say, I'm a bad wittle boy."


9. Homer Simpson

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While we're on the subject of suicide (What a great way to end a list about a beloved cartoon, huh?) let's talk about the time in that Homer casually decides to off himself by tying himself a boulder and drowning himself. No, seriously, it happened. In the season one episode "Homer's Odyssey", Homer gets fired from the nuclear plant, and after an unsettling scene in which he breaks open his 10 year old's piggy bank in an attempt to steal beer money, Homer leaves his family a note and heads for a bridge. He is only stopped when his family follows him, and is almost run over by a car. This spurs Homer to lead a crusade on safety which gives him a new lease on life and eventually leads to him being offered a new job at the plant. So yeah, if you've ever wondered how Homer got his job as safety inspector, that's the reason...the deeply upsetting reason.

Key Line: `Dear Family.  I am an utter failure, and you'll be better off without me.  By the time you read this, I will be in my watery grave.' (An excerpt from his actual suicide note...Have a nice day...)