The Simpsons is one of the longest-running programs in television history. With an amazing thirty seasons under its belt, the show has been a pop culture icon for decades and remains one of the most beloved shows off all time. But after all that time, some aspects of the show might not stand up to the test of time.
Many Simpsons episodes are timeless and still rewatchable, but there are some that are products of their time. They feel out of place and inappropriate watching them after all these years. While the show can boast an impressive number of brilliant episodes, here are some episodes of The Simpsons that have not aged well.
10 The Principal And The Pauper
"The Principal and the Pauper" is a rather notorious episode in The Simpsons' history. The episode reveals the man we have always known as Principal Seymour Skinner is actually an imposter. However, by the end of the episode, the town decries that they will just forget that matter and go on with their lives.
At the time, the shockingly lazy writing of this episode seemed like an outlier in the normally excellent show. However, all these years later, the episode is still insultingly bad and now seems like a sign of the eventual decline in quality for the once-great show.
9 Beyond Blunderdome
Several episodes of The Simpsons have centered around celebrities playing themselves and it's always a bit risky. For one, it seems like a pandering gimmick, but there's also the chance the celebrity will have a significant fall from grace, like this example.
"Beyond Blunderdome" finds Homer helping Mel Gibson improve his latest movie. There's some amusing stuff in the episode, but with Gibson's frequent controversies, he's far from the beloved movie star he's depicted as in this episode. It's a little strange to see him this way.
8 A Star Is Burns
Crossover episodes are a difficult thing to get right, and after all these years, this particular attempt feels more and more like a miss. The episode finds Jay Sherman, the main character of The Critic coming to Springfield to host a film festival.
Despite giving us the classic "Boo-urns" joke, the desperate attempt to promote another Fox show on The Simpsons felt really awkward. It was also not a popular idea with The Simpsons' creators. And now after all these years, with The Critic a largely forgotten show, it feels even odder.
7 Last Temptation Of Homer
With a show being on the air for so long, it is only natural that the writers would want to push the characters to new places occasionally. However, it can become problematic when they show a side of a beloved character that audiences don't want to see.
In this episode, Homer is fighting the mutual attraction between himself and a new co-worker. While the fact that Homer doesn't act on the impulses is meant to be honorable, looking back, he doesn't come off so well. With Marge sick at home, Homer seems extremely selfish for almost seeking out a more attractive partner.
6 The Way We Was
"The Way We Was" is a charming flashback episode that shows the early romance of Homer and Marge – which was foolishly retconned in later years. The episode shows Marge and Homer meeting in high school and making plans to go to prom together, only for Marge to go with Artie Ziff instead.
After the prom, Marge is with Artie who becomes aggressive with her in the backseat of a car. While this ultimately pushes Marge towards Homer, the show really glosses over the uncomfortable sexual misconduct that occurs.
5 Homer Loves Flanders
The fact is that as society changes and events unfold, some images that were once acceptable become distasteful for modern audiences. In this episode of the show, Homer grows to see Ned Flanders as a friend only to annoy Ned to the point where he's ready to snap.
In a dark dream sequence, Ned marches to the top of a tower with a rifle and begins firing at the people below, imagining them as Homer. It is a shocking moment to think about now and given some of the horrific events that are still etched in our minds, it is a disturbing image to watch.
4 The City of New York vs. Homer Simpson
The Simpsons has been acknowledged in the past for its eerie talent for predicting future events. In the case, of the episode "The City of New York vs. Homer Simpson", such eerie omens make it difficult to watch.
The episode does nothing wrong itself, but the New York City-set story which prominently features the World Trade Center invokes a lot of 9/11 images. It is all pure coincidence, but some of the jokes and comments in the episode make it impossible not to think of that tragedy.
3 Much Apu About Nothing
In recent years, The Simpsons have been called out by some critics for the depiction of the character Apu. There was even a documentary called The Problem with Apu which discussed the character's offensive stereotyping. Though Apu has been a character on the show for years, the controversy made it hard not to see him differently.
This specific episode that centers around Apu trying to become an American citizen is especially uncomfortable now. Not only are some of the more offensive aspects of the character put on display, but it gives Homer a somewhat anti-immigration stance which is unpleasant to watch.
2 Homer's Phobia
As we've seen on this list, as flawed as Homer Simpson can be, it's not fun to see him become an all-out jerk. So in an episode dealing with homosexuality, Homer's views on the matter are certainly cringeworthy.
The episode shows Homer shocked to discover the family's new friend John is gay. While the episode ultimately shows Homer's homophobic views are foolish, seeing him take such a hateful stance makes him very unlikable. To add to that, he almost forces Bart to murder a caged animal to prove he's a man.
1 Stark Raving Dad
For The Simpsons to get Michael Jackson to prominently guest star on the show was a pretty big deal. Even though he was using a false name in the credits, the massively popular popstar was very recognizable in the plot about Homer meets a man in an asylum who thinks he's Jackson himself.
Obviously, Jackson's reputation has suffered since then. Sexual assault accusations against Jackson have been thrown at Jackson repeatedly throughout the last few decades. The new documentary Leaving Neverland goes into disturbing detail about the accusations, which has severely damaged Jackson's reputation.