Fox
When "The Simpsons" has the kind of legendary run it had from season 3 to season 8, no episode could knock it from the pantheon of greatest TV shows of all time. The likes of "Lemon of Troy" and "Marge vs. the Monorail" rank among the best "Simpsons" episodes of all time as instantly rewatchable sitcom classics that manage to cram in memorable jokes over a span of 22 minutes. Of course, we're a long way from season 8 at this point, and one could argue there are more bad episodes than good ones by now
That isn't to say everything post-Golden Era is irredeemable. There have been some real gems over the years; it's just not as consistently great as something like season 5 where every episode is a banger. Even then, there's a marked difference between an episode that's just kind of forgettable and something that actively makes you upset.
Nearly 800 episodes of "The Simpsons" have come out over the years, with more on the way. During that time, "The Simpsons" has put out some storylines that are genuinely baffling in hindsight. They're the kind of stories that make you scratch your head and wonder who thought this was a good idea, whether something is in poor taste or goes against pre-established character traits. As Comic Book Guy would say, these are the Worst. "Simpsons." Storylines. Ever.
The Boys of Bummer (Season 18, Episode 18)
Fox
The following slide contains references to suicide.
We're all for a little dark humor, but when a TV episode borders on incessant cruelty rather than humorous commentary, it's hard to watch. Season 18's "The Boys of Bummer" opens with Bart failing to catch a pop fly during a championship game against Shelbyville, causing the entire town of Springfield to turn against him. Everyone bullies Bart incessantly, to the point where he snaps and begins spray painting "I Hate Bart Simpson" across town so that he can show everyone that he's on their side. At one point, he gets up on a water tower where Chief Wiggum encourages him to jump, which he does and fortunately lands in some bushes.
The entire plot hinges on a town of adults bullying a child to the point he's willing to take his own life. One could view this as commentary on how far sports fans are willing to go in expressing their disdain toward players who make simple mistakes. One could almost view "The Boys of Bummer" being akin to the Britney Spears episode of "South Park," where the show was ahead of the curve in dissecting how society so cruelly treats public figures. Sadly, "The Simpsons" isn't able to thread that needle between humor and commentary as well, so it comes off as unpleasant to watch.
Of course, the townspeople apologize for their behavior (eventually) and stage a fake game to boost Bart's self-esteem. The message only seems to be, "Don't bully children," which should really go without saying.
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Days of Future Future (Season 25, Episode 18)
Fox
Season 23's "Holidays of Future Passed" is actually one of the more underrated "Simpsons" episodes of the modern era. It's a flash-forward episode, only instead of Lisa being President of the United States, she's married to Milhouse and dealing with a rebellious daughter. Bart's divorced and struggles with watching Homer be a great grandfather to his kids when he was such a lousy dad toward him. There's humor and heart as the show offers a glimpse into what the future could reasonably hold for Bart and Lisa. It's such a shame it's spiritual sequel — season 25's "Days of Future Future" — drops the ball so hard.
Instead of sentimental character arcs, "Days of Future Future" opens with Homer dying repeatedly while getting replaced by clones before ultimately winding up in a computer. Lisa's more attracted to a zombie Milhouse than regular Milhouse, and Bart tries to make things work with his ex-wife while working at Cretaceous Park. It feels like the episode is more interested in pursuing "Treehouse of Horror"-esque plotlines rather than really diving into how these characters would be 30 years in the future.
Plus, the episode just ends up being Bart's fantasy while he was getting his mind wiped, a la "Eternal Sunshine of the Spotless Mind." The reveal means one can't help but ask, "What was the point of all this?" To be honest, you could ask that for much of later "Simpsons," but after seeing that the show could still soar with "Holidays of Future Passed," this one just feels like phoning it in.
Homer vs. Dignity (Season 12, Episode 5)
Fox
I'll go ahead and say it: I don't think season 9's "The Principal and the Pauper" is where "The Simpsons" jumped the shark. It's understandable why some people tout it as that moment, with Principal Skinner revealing he isn't actually Seymour Skinner, and "Simpsons" creator Matt Groening has also voiced how much he believes that episode was a mistake. But it's still a funny episode with meta humor dissecting how ridiculous this show can become and still resort to the status quo, because that's simply what all sitcoms must do. The actual point where "The Simpsons" starts it's decline is season 12's "Homer vs. Dignity."
No list of the worst "Simpsons" storylines would be complete without this episode, where Homer becomes Mr. Burns' "prank monkey," humiliating himself to earn money for his family. It's a standard "Simpsons" set-up where the family has money trouble, and Homer goes to extreme lengths to help them. However, the episode takes things a step too far when Mr. Burns has Homer dress up as a female panda that's electrocuted by zookeepers and then taken by the male panda to ... mate.
Homer getting sexually assaulted by a panda just leaves a bad taste in the mouth. "The Simpsons" would occasionally offer some gross-out, dark humor, but this feels like an attempt to get on the level of something like "South Park" or "Family Guy." It was ill-fitting for "The Simpsons" and the much clearer sign the show was running on fumes and resorting to gags in poor taste.
The Strong Arms of the Ma (Season 14, Episode 9)
Fox
This slide contains references to sexual assault.
Far be it from us to say there are certain topics that are off-limits when it comes to comedy. But as should be clear from this list, certain subjects just don't work well within the context of a primetime animated sitcom, which is evident that there are now multiple episodes where Homer gets sexually assaulted.
In season 14's "The Strong Arms of the Ma," the assault comes from his wife, Marge, who begun working out after a traumatic experience, which eventually leads to her taking steroids. The episode could be seen as a cautionary tale of the substance, with Marge's anger flying out of control in many instances. During one scene, Marge wants to get intimate while Homer's against it, and from the fact he's sore the next morning, it's clear Marge got her way.
The scene plays into a troubling trope in media where sexual assault against men is played for laughs. "The Boys" season 4 continued this awful, unfunny trend with Hughie's (Jack Quaid) assault getting downplayed, and "Family Guy" had a similar scene of Lois taking advantage of Peter. If the roles were reversed, there's no way it would've even made it out of the writers' room, as it would've been transparently horrific. An episode spouting the dangers of steroid use could've been worthwhile, but as it stands, "The Strong Arms of the Ma" probably gets skipped in most people's rewatch marathons.
If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).
The Sweetest Apu (Season 13, Episode 19)
Fox
Some great "Simpsons" episodes have come from characters feeling tempted to have affairs, like "Life on the Fast Lane," where Marge gets tempted to cheat on Homer with Jacques, and "The Last Temptation of Homer," where Homer feels the urge to sleep with a co-worker. Such temptations are natural, and both episodes end with each character reaffirming their commitment to their marriage. Sadly, Apu didn't receive a similar revelation.
In season 13's "The Sweetest Apu," Homer discovers that Apu is having an affair with a woman who delivers the Squishee syrup to the Kwik-E-Mart. Apu's wife, Manjula, eventually discovers his infidelity, kicks him out, and threatens divorce. It's all honestly pretty sad, and it forever tainted Apu's legacy. Up until this point, he'd been a great side character with a surprising amount of depth, whether it involved teaming up with Homer to try to get his Kwik-E-Mart job back or teach the Simpsons about how essential immigrants are to the fabric of America. He'd been a great guy ... up until now.
After convincing from the Simpsons (and meeting a divorce lawyer who may have been a demon), Manjula gives Apu another chance when that probably wasn't the best call. Yes, they have eight children together, but their relationship continues to be stressful even after "The Sweetest Apu" is over. Apu's infidelity comes up throughout the series, like in season 14's "Brake My Wife, Please," when Apu and Manjula are seen in couples' counseling, where she elbows him in the stomach. "The Sweetest Apu" shows divorce as an awful thing that should be avoided at all costs, but if Manjula's still violent with Apu after so much time, maybe a separation would've been for the best.
Every Man's Dream (Season 27, Episode 1)
Fox
"Every Man's Dream" basically became every "Simpsons" fan's nightmare. After years of possible infidelity plotlines between Homer and Marge, the pair actually split up with Homer sleeping with a much younger woman, Candace (voiced by Lena Dunham), in season 27.
Only he doesn't actually sleep with Candace, because the whole thing turns out to be a dream. It's not just one dream either, as the episode repeatedly shows characters waking up to show how what we've just seen didn't actually happen, culminating in Hannah Horvath (Dunham's character from "Girls") talking about tattoos. It's less of a commentary on the nature of Homer and Marge's relationship and more of "The Simpsons" trying to capitalize on the success of "Girls" at the time, which is evident from the fact that Allison Williams, Zosia Mamet, and Adam Driver also guest star.
"Every Man's Dream" feels like it was designed to renew interest in the series 27 seasons in. I remember the promos for this clearly of how Homer would date Candace, and it felt like such a betrayal. The fact that none of it actually happens feels like the show having its cake and eating it, too. It wanted to get people talking about "The Simpsons" again without doing anything to upset the status quo.
Co-Dependents Day (Season 15, Episode 15)
Fox
Why does Marge put up with Homer? It's a question that may baffle some viewers even though Homer has shown he can be a loving father and husband from time to time, but usually, his kindness only comes after he messes up majorly. Still, Marge always finds a way to forgive him, which sometimes requires huge leaps in logic, which is the case for season 15's "Co-Dependents Day."
Marge and Homer's relationship starts going amazingly after she begins drinking with him after a trip to wine country. After Oktoberfest, Homer (while drunk) drives them home and overturns the car. Rather than risk another mark on his record, he puts Marge in the driver's seat, so the cops think she crashed the car. It's a pretty despicable thing, even though Homer tries to justify it by assuming Marge would just get a slap on the wrist. Marge even goes to rehab and ... wait, what? Homer's driven drunk plenty of times, and the most he's ever endured is going to Alcoholics Anonymous meetings in season 4's "Duffless." Even if Marge genuinely drove drunk, it's still a drop in the bucket (literally) compared to how Homer's drinking has harmed himself and his loved ones.
Homer thoughtlessly giving Marge a bowling ball for her birthday is bad, but him framing her for his mistakes feels like a step too far. Of course, Marge forgives him because she realizes she didn't like drinking, and she liked spending time with him. It's a quick turnaround from when she discovers his betrayal, and honestly, if Marge wanted to separate from him right then and there, no one could blame her.
What to Expect When Bart's Expecting (Season 25, Episode 19)
Fox
Every so often, "The Simpsons" puts out an episode that just kind of baffles you. It's almost like everyone has realized they've done all they can do with these characters, so they start doing the most random things that border on inappropriate. That's the case with "What to Expect When Bart's Expecting." Bart wants to get rid of his art teacher, so he uses some voodoo supplies to give her a stomachache, only for her to show up pregnant. This causes everyone at Springfield Elementary to talk about how "Bart got a teacher pregnant," which doesn't sound great. From here, Bart starts up a fertility clinic to help other couples conceive, and Fat Tony hires Bart to get his prized racehorse pregnant.
What is this? It feels like someone thought it would be funny for someone to say how Bart got a teacher pregnant only for there to be a revelation that it isn't what it sounds like. After that reveal, everything goes off the rails, with Fat Tony's inclusion really coming out of nowhere. Word to the wise, if Fat Tony and the mob show up suddenly in the third act, it's probably because they didn't know how to heighten the episode any further without bringing in the threat of gang violence.
Combined with the revelation Fat Tony's horse is gay, it all indicates the episode's going for some "lol so random" humor, and it just doesn't work. Bart should be cutting the heads off statues or getting in trouble for shoplifting, not promising couples he can help them get pregnant, which feels so weird to type.
Jazzy and the Pussycats (Season 18, Episode 2)
Fox
"Simpsons" episodes don't necessarily need firm morals, as Homer famously once declared, "It's just a bunch of stuff that happened." But if an episode is going to try to have an emotional core, it shouldn't get it completely backwards. In season 18's "Jazzy and the Pussycats," Bart practices the drums and becomes a well-regarded musician within the jazz community, much to Lisa's dismay, as jazz has always been her passion. However, rather than have Lisa accept that it's okay if her brother is better than her at something, she starts rescuing animals, one of which bite's Bart's arm.
It wasn't directly Lisa's fault, with the whole animal plotline coming out of nowhere halfway through the storyline, but Marge talks with Bart about how she only rescued those animals because she felt bad over being upstaged. Lisa feeling upset shouldn't be Bart's fault. Bart's a notoriously troubled kid, and he finally managed to get his aggression and energy out in a creative outlet. Everyone should celebrate Bart's accomplishments rather than hold him back just so Lisa continues feeling special.
At a benefit concert to raise money for Bart's injured arm, he winds up giving the money instead to build an animal sanctuary. Lisa gets everything she wants at the end — a place for the animals and Bart never drumming again. There's no need for fighting over who's a better jazz musician, as it's something both Bart and Lisa could excel at. But with Bart seemingly quitting jazz for good, his only hope for a good career is to one day become Chief Justice of the Supreme Court.
Love is a Many Strangled Thing (Season 22, Episode 17)
Fox
Homer strangling Bart is one of the oldest gags on "The Simpsonsm" even though it's absolutely child abuse. Everyone just kind of overlooks it, but the show has attempted to grapple with this punishment before, like in season 22's "Love Is a Many Strangled Thing." Homer tickles Bart at a football game, causing him to wet his pants in front of everyone, so Homer attends therapy to learn to be a better father. It's here that Dr. Zander (voiced by Paul Rudd) learns Homer strangles Bart regularly, so he brings in Kareem Abdul-Jabbar to strangle Homer to break him of this habit. It works, but Bart becomes a total sociopath, now that no one can physically harm him, and he even annoys Dr. Zander to the point where he tries to kill Bart.
So is the message that Homer needs to strangle Bart to keep him in line? The father and son end up reconciling by the end, but the whole storyline paints their relationship in such a dark light. Everyone just kind of shrugs their shoulders and realizes that Homer abusing Bart is a necessary evil. "The Simpsons" used the strangling bit for decades at this point, but this is really the first time it hones in on it. Maybe it would've been better if everyone just kept turning a blind eye, like how everyone's cool with "Pokémon" essentially being animal fighting simply because the critters are so darn cute.
Don't worry, true believers. "The Simpsons" brought back the neck-strangling for season 36, so we can all continue enjoying watching Homer assault his child until the heat death of the universe finally brings this show to a close.