The Simpsons is one of the best television series ever created. It’s coming close to becoming the longest-running prime time series in history, and has managed to influence entire generations of fans and audiences. The absurd adventures and tribulations of Homer, Marge, Bart, Lisa, and Maggie have entertained people for over thirty years, and the show hasn’t slowed down in the slightest. But the fun family stories have also managed to explore incredibly heavy and depressing story lines.
Many of the side characters in the franchise have been given dark, depressing backstories that would rival any indie drama. And even the main family has been revealed and twisted over the years, becoming increasingly complicated. The show is largely about people trying to live their lives in a world where they just can’t seem to win. The world is against them, and there’s no amount of silly jokes or clever wordplay that can help the characters escape their innate faults and inner demons. These are the fifteen of the darkest things that have ever come out of The Simpsons that you never realized watching the show over the years. And, heads up, spoilers are coming.
15. Everything To Do With Sideshow Bob
Played by Kelsey Grammer, Sideshow Bob has been one of the more famous recurring aspects of the series. The character originally appeared in the very first season, trying to frame Krusty for armed robbery in an attempt to steal his show out from under him. Bart manages to uncover the exact evidence needed to exonerate Krusty, and sends Bob to jail. But the intellectual would-be thief would return every couple of seasons with a new evil scheme – but now, he’s skipping the subterfuge and going straight to attempted murder. He’s tried to kill his new wife Selma, ten-year-old Bart, his former employer Krusty, and various others in his rage. He even once detonated a nuke with the intention of destroying all of Springfield, but the bomb turned out to be a dud. Even recent years haven’t seen him calm down. At one point, he even cut the face off a fellow prisoner in jail and sewed it onto his body so he could escape. The original Bob was a fun villain for an absurd but still relatively down-to-earth sitcom. Now, he’s a full-on movie monster.
14. Nelson And Milhouse Both Come From Terrible And Depressing Broken Homes
Over the course of the series, two of Bart’s friends and Lisa’s love interests have grown into their own fleshed-out characters: the nerdy blue-haired Milhouse, and the perpetually sleeveless bully Nelson. But as part of their definition and contrasts with Bart, both come from completely broken homes that fell apart in different ways. In both cases, money is always a problem that seeps down from their parents and has a negative effect on their lives. With Milhouse, his parents’ marriage fell apart before his eyes and he watched as his spineless father degraded further and further into a pathetic sad sack that the entire town makes fun of. Meanwhile, Nelson barely knows his father. His dad skipped town years ago, leaving Nelson in the care of his alcoholic, uncaring mother. The two live in a wreck of a house that he does his best to hide from others. Both are established as intelligent and gifted young men, but their situations and upbringings have helped transform them into shells of what they could have been. Bart got off lucky.
13. Ned Flanders Is A Lonely Two-Time Widower
The next door neighbor to The Simpsons since the series began, Ned Flanders has lived a devout and blessed life. Mostly. While he seems to have perpetually good luck and is maybe the nicest man in town, he’s also had a very specific aspect of his life become increasingly sad over the years. Ned is a two-time widower, having lost his first wife Maude to an errant t-shirt cannon (because of Homer, naturally). His period of grief was altogether brief, however, as he started seeing other women in an attempt to move on. It wouldn’t be until Ned met Edna Krabapple, Bart’s long-suffering 4th grade teacher, that he really found happiness again. Their relationship was actually an incredibly sweet and healthy coupling, and they brought the best out of each other. But then Marcia Wallace, the actress who played Krabapple, tragically passed away. In respect, the show quietly killed Krabapple off-screen, leaving Ned alone again. Maybe the only plus side has been Homer’s increasingly better relationship with him.
12. Barney’s Failed Attempts To Go Sober
Barney Gumble has been Homer’s best friend since the early days of the show, but he’s been slowly phased out of the series over the years. Part of it probably stems from the rising prominence of Lenny and Carl, but his overall development as a character probably played a role, too. See, Barney was an incredibly talented young man who became a drunken wreck thanks to his friend Homer. Taking the drinking completely out of hand, Barney became a wreck in a city full of them. In the 12th season, he tried to kick the habit and clean up his act. But this only lasted a few years, and Barney has fallen back into booze. He only appears briefly now, and the audience never knows what version of him we’re going to get: the clean, sober Barney, or the wreck of a human being. And that’s just too sad of a reality for The Simpsons.
11. Moe Has Tried To End His Own Life On Screen
Moe is the crotchety and cheap bartender of, well, Moe’s. He’s constantly angry, disturbing in his attractions to women, and consistently reminded by the world that he’s an ugly piece of dirt. And the thing is, he agrees with all that. He thinks he’s horrible. It’s why he’s tried to end his life so many times. It’s been played for laughs in some of the darker episodes of the show (like the Christmas episode where he tries and fails to kill himself five times). But some of the later episodes, especially in season 24’s “Whiskey Business”, his suic*dal tendencies have been played horrifyingly straight. At one point, he actually put his head through the noose and called the suicide hotline, only to be put on hold and pranked by Bart. When he slips and knocks his chair over, it really looks like the end for him. Homer, Lenny, and Carl find him and save him in time, but for a moment it looked like The Simpsons was about to do something even brutal shows have trouble depicting.
10. Grandpa Simpson Is SUPER Sad And Depressed Living Alone In A Retirement Home
Abraham Simpson – a.k.a. Grandpa Simpson – has been terrible to people all his life. His quiet abuse of Homer while raising him helped morph Homer’s outlook on life and turn him into the man we know him as. He discouraged Homer from any of his passions or dreams, and belittled him at every opportunity. While he did love his son, his own anger and failings shaded their relationship. So when Homer took his father to a retirement home and left him there, Homer saw it as almost as revenge for his troubled childhood. But the rest of the family has often forgotten about him in the process, leaving him to grow older and senile alone. And as he’s proven time and again, his antics (like driving through the mall or mistaking a hot iron as a phone) make him a danger to himself and others. He’s not a healthy old man, and the fact that his family doesn’t care enough to fix it doesn’t help.
9. Homer Is Legit Abusive To His Family
Homer Simpson is one of the most simple characters in fiction. He’s a passionate man who enjoys happiness, whether it comes from a hug or a drink. He’s a good man at his core, and quick to befriend anyone. But that passion makes him quick to anger too, and often in an uncontrollable way. He gets angry and acts out in a way that no one should replicate. Here we are thinking of the “running gag” of Homer strangling his son. During the Family Guy crossover with The Simpsons, even the pretty horrible Peter Griffin is horrified by this tendency of Homer’s, and he’s not wrong. Some episodes have even shown Milhouse watching the abuse, and looking on in sheer terror. It’s played as a joke constantly, but the second it’s played straight it becomes frightening. And that’s before the kind of indifference he showcases towards Lisa and Maggie, which borders on sheer abandonment at times.
8. Maggie Might Be A Psychopath
The smallest of the Simpsons, Maggie has proven to be an incredibly brilliant baby. She’s displayed an aptitude for music and knowledge well beyond her age. But she’s been showing some disturbing signs along with that intelligence, and none of them speak well of her future mental health. After watching an Itchy and Scratchy cartoon, she decided to imitate the act and ended up bashing her father with a mallet. In another famous moment, she ended up pulling the trigger on the gun that almost killed Mr. Burns. And while most of the town comes to the conclusion that it was an accident, the ending implies that Maggie was maybe a little more knowing when she fired that gun. It’s not the first time she’ll end up firing a gun at someone, with an episode even revealing that she hides a bolt action rifle under her crib that she uses to protect her family. That’s some serious murderous abilities right there.
7. Lisa Is Depressed, Like, A Lot
Lisa Simpson is usually portrayed as the smartest member of her family. She’s usually the one figuring their way out of whatever problem they’ve found themselves in. But while all that intellect and skills are useful in the stranger situations they deal with, they are less useful when they’re just trying to live. Lisa finds herself isolated from the other students. She’s largely friendless, and usually portrayed as one of the least popular students at her school. She can’t even connect properly with her parents on any serious or intellectual level. And any time she finds some kind of happiness, it’s taken away from her at the end of any given episode. And the future episodes we’ve seen of her adult life show her a successful member of society but still sad about her seemingly perfect life.
6. Bart’s Potential Goes Nowhere
Over the course of the series, Bart Simpson has become something of a hardcore troublemaker. He’s sarcastic, mean spirited, and confrontational. It’s all the stuff you expect to see with a potential felon, but here’s the thing: Bart is way more than that. He’s effortlessly artistic, becoming a famed graffiti artist in just a few weeks. He picks up instruments and languages in hours alone, and can master them in days. He’s an artistic genius, but no one recognizes that. Instead, they lay all the possible accolades and achievements on Lisa. And while Bart may be more popular and sociable than Lisa, that still manages to tear down his self-esteem. And when we get to see the future laying ahead of Bart, it gets worse. He starts his own artistic business, but it’s not able to go anywhere. He ends up as an office drone with two children and a divorced wife, leading a quiet and depressed life, which we found out in a Christmas episode. Jeez, The Simpsons.
5. Marge Is The Ultimate Enabler
Marge Simpson is a truly tragic character. She was a young woman full of promise and potential that found herself trapped in a world she never expected to be living in. Despite all her academic and artistic achievements, she never had the chance to follow through with her passions. Instead, she ended up falling in love with Homer and being brought down to his level. She’s constantly trying to bring her family back up to a higher status of life, but she can never keep their innate nature and crazy instincts from peaking through. She has trouble finding a happy middle, expecting the best results and not willing to compromise. It results in her being a weirdly passive character, even considering her reactionary nature. She doesn’t stop Bart or Homer from going off and performing increasingly worse and worse acts.
4. The Show Has Enraged Everywhere They’ve Vacationed
Over the course of almost thirty years, the Simpsons have traveled all around the world and explored all kinds of cultures. But the family hasn’t always approached them from a completely even-minded approach. Their travels have gotten the creators of the show in trouble from time to time, especially when their adventures around the world end up attracting international attention. People from Australia and Japan were incredibly offended by the depictions of their countries, as they were very stereotypical depictions of their nation. And when the family went to Brazil and portrayed it as a dirty world filled with ferocious monkeys, the nation demanded a formal apology from the cartoon. It’s not like the cartoon ever really apologized for the routine, but sent the family back to the country ten years later in a different episode (this time mocking the World Cup and political shifts in the nation) with even worse results.
3. The Family Guy Joke
So, the previously mentioned Family Guy/Simpsons crossover wasn’t the first time the two franchises ran into each other. Following a jab from The Simpsons (where Peter Griffin was used as the example for plagiarism in a dictionary), the fellow Fox show decided to respond with an attack back. But they decided to take it a step way too far with their response. In a play on the ads that run at the bottom of episodes, Marge Simpson walked on to advertise The Simpsons. Resident Family Guy predator Glen Quagmire attacks her and tries to force her on the ground. Marge manages to escape, only to be impressed off screen and she ends up inviting him back to her house. At which point, Quagmire follows her home, Homer stumbles in on them in bed, and Quagmire ultimately shoots and kills the entire family in their house. WOW. It’s one of the darkest things that show has ever done (which is saying something), and feels needlessly frightening and sickening.
2. The Reason We Never Saw More Lionel Hutz Or Troy McClure
During the golden age of The Simpsons, two of the most memorable recurring characters were the inept lawyer Lionel Hutz and the increasingly weird C-list actor Troy McClure. They were both mainstays of the series in the earlier seasons, and often the best parts of the episodes they appeared in. But there’s a reason they disappeared from the show. They were both played by famous SNL actor Phil Hartman, who had been appearing regularly in various shows and movies. But Hartman’s wife, Brynn, had a troubled history with drugs. The two got into a shouting match, and Hartman threatened to leave her if she couldn’t get her addictions under control. That night, as he slept, Brynn went into the room and shot him in his sleep. She eventually turned the gun on herself, shocking the comedy world. The characters were retired in tribute to Hartman.
1. The Springfield Police Might Be The Worst Cops In America
Chief Wiggum is hilarious, no doubt about it. But from the perspective of the characters in the universe, having him as a figure of authority must be constantly stressful. The police force are hilariously caviler and open with their stance on bribery and extortion (i.e. they love it), and have even arrested people for failing to pay sudden surprise fees. They only engage in actual criminal investigation when they get a little kickback for their troubles. And they wrongfully arrested a LOT of people over the years but never faced any real form of internal investigations. What few good cops do patrol the city have to contend with one of the most aggressively stupid characters in all of fiction, Chief Clancy Wiggum. This is a guy who rubs his temple with the barrel of his gun, and he’s technically one of the most powerful men in town. Living in a place like that, no wonder there are always riots.
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