10 ‘Simpsons’ Jokes That Have Become Embarrassingly Outdated

Just cause the show lasts forever, doesn’t mean the jokes do
10 ‘Simpsons’ Jokes That Have Become Embarrassingly Outdated

For more than 30 years, The Simpsons has been unleashing joke after joke after joke, and as the cruel passage of time moves forward, some of those gags lose their relevance. Sometimes the bit is tethered to a reference that has fallen into the Springfield Gorge of obscurity. Other times, circumstances have so drastically changed that it makes the joke’s entire foundation crumble. 

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At any rate, the following are the timely Simpsons jokes that mustered hearty laughs when they aired in the 1990s but are now met with blank stares at best or overwhelming cringe at worst...

‘The next time the Yankees win the pennant’

Episode: “Bart Gets Hit by a Car,” Season 2, Episode 10

The New York Yankees are notably one of the greatest teams in Major League Baseball history. But in 1991, the Yankees franchise was a shell of its former self, having not made the postseason in nearly a decade. The previous season, they had finished in last place for the first time in 24 years, with a record of 67-95. 

This made them prime fodder for The Simpsons. When Bart arrives in Hell after getting hit by Mr. Burns in his car, the Devil seems surprised to see him. “You’re not due to arrive here until the next time the Yankees win the pennant,” he explains. “That’s nearly a century from now.” Things were that bleak. 

Of course, after a complete overhaul, the Yankees won the pennant (and World Series) five years later in 1996, as well as in 1998, 1999, 2000 and 2009. Somehow Bart still managed to dodge going back to Hell.

‘Aww, the Denver Broncos!’

Episode: “You Only Move Twice,” Season 8, Episode 2

Outside of five outstanding seasons in the late 1970s and late 1980s, the Denver Broncos had never really been that notable of a team in the NFL since their founding in 1960. Although Homer once dreamed of being John Elway, his favorite team has always been the Dallas Cowboys, which is why when mega-millionaire Hank Scorpio rewards him with an NFL team for helping out with his plot to seize the East Coast, Homer is disappointed to find out it’s the Denver Broncos. The team is portrayed in the scene as bumbling athletes who fail to throw, catch and tackle properly.

In early 1996, when the episode was being produced, the team had just finished a mediocre season with an 8-8 record. However, this joke quickly became outdated. By the time the episode aired in November, the team had already turned into a powerhouse, topping the AFC West weeks after the episode aired. The Broncos would go on to win the Super Bowl the following season in 1998 (and then again the season after that).

After expressing his disappointment, Marge tells Homer, “I think owning the Denver Broncos is pretty good!” But Homer rejects her thought, stating, “You just don’t understand football, Marge.” 

‘I don’t see any cameras’

Episode: “Beyond Blunderdome,” Season 11, Episode 1

Robert Downey Jr. is a beloved and versatile actor, most notable to modern audiences as Tony Stark/Iron Man in the Marvel Cinematic Universe. Unfortunately, throughout the latter half of the 1990s and early 2000s, Downey dealt with high-profile substance abuse, arrests, stints in rehab and drug relapses.

When the Simpson family is traveling around Hollywood with Mel Gibson in 1999’s “Beyond Blunderdome,” Homer spots what appears to be a movie being filmed. Marge exclaims, “Look! They’re making a movie! Robert Downey Jr. is shooting it out with the police!” Bart is confused, however, noting, “I don’t see any cameras.”

Thankfully, Downey has been clean and sober for 20 years, so this joke might confuse those who didn’t grow up in the 1990s. Additionally, the fact that the Simpsons are hanging out with a seemingly-normal Mel Gibson throughout most of the episode might confuse newer viewers as well.

‘Oh no! Beta’

Episode(s): “Saturdays of Thunder,” Season 3, Episode 9, and ‘Itchy & Scratchy: The Movie,’ Season 4, Episode 6

Betamax (or “Beta”) was one of the earliest videotape recording systems produced, hitting the market in 1975. VHS soon followed in 1976, beginning a videotape format war that Beta ultimately lost, not due to its quality, but due to the greater affordability and format support from movie studios that VHS attained in its first decade or so.

Although Sony produced Betamax players through 2002, Beta had received such a reputation as the format “loser” by the early 1990s that The Simpsons writers wrote two gags poking fun at it. When the Simpsons go to rent a video, we see the local video store is named VHS Village, but they were formerly The Beta Barn. In another episode, when prisoners wreak havoc on Springfield after a prison break, Snake laments that the video player he’s stolen is Betamax format. Hard to believe we’re now two formats removed from VHS (and almost physical media) these days.

‘Property of Blockbuster Entertainment’

Episode: “Homerpalooza,” Season 7, Episode 24

Many folks still remember them, but Blockbuster was a video rental business that started in 1985. By the mid-1990s, it had become a multi-billion-dollar company, expanding into music and film production. They had become so big, in fact, that The Simpsons joked they could even attain ownership of stray children.

“We have a lost child here,” Cypress Hill lead singer B-Real announces to the Hullabalooza music festival crowd in 1996’s “Homerpalooza,” continuing, “If she is not claimed within the next hour, she will become property of Blockbuster Entertainment.”

Blockbuster, of course, went into decline within a few years, as Netflix started its direct-to-home DVD rentals. By 2010, they filed for Chapter 11 bankruptcy protection and now only have one store left after a peak of more than 9,000 in the mid-2000s.

‘They stick all the jerks in Tower One’

Episode: “The City of New York vs. Homer Simpson,” Season 9, Episode 1

The World Trade Center towers had been an iconic part of the NYC skyline for 20 years when The Simpsons visited in 1997. The location played an integral part in the episode’s plot, as Homer’s car is booted and ticketed multiple times in the WTC’s plaza. Many jokes related to the buildings are made. In the middle of an argument between tenants of each tower, one exclaims to Homer, “Sorry about that guy! They stick all the jerks in Tower One!” (Bill Oakley, showrunner for the episode, later called the joke “regrettable.”)

After 9/11, the episode was removed from syndication for years. Once it returned, it was heavily edited to remove any jokes about the towers and cut shots that included them. The treatment of the towers in the episode has even led to conspiracy theories. The unedited episode, however, now appears on Disney+.

‘Name one person who’s gotten rich by doing yo-yo tricks’

Episode: “Bart the Lover,” Season 3, Episode 16

This joke isn’t so much outdated but remarkable in its context. Sometimes, as years pass, people just aren’t the same to society at large, giving a whole different vibe to what was essentially a throwaway joke in 1992’s “Bart the Lover.”

Homer thinks Bart is going to make the family rich by doing yo-yo tricks, but when Marge asks Homer to name one person who’s actually done this, two of the three names he thinks about have a totally different public perception today. Thinking to himself, he wonders, “Donald Trump? No. Arnold Palmer? No. Bill Cosby? No... D’oh!

Thankfully, Palmer hasn’t done anything controversial, and he died in 2016, so his legacy is clean — for now.

‘He thinks he’s one of the ‘Models, Inc.’’

Episode: “Two Dozen and One Greyhounds,” Season 6, Episode 20

The Simpsons are great at calling out shows they recognize as duds. After all, they have a history of being a lead-in to them

In this gag, the family is watching TV together with their greyhound puppies, and one adorably stands up and touches the TV when a model appears on it. “Look at Branford II,” Marge exclaims, “He thinks he’s one of the Models, Inc.

Models, Inc., a spinoff of Melrose Place, only lasted one season and was already canceled by the time this episode aired (it may have been canceled even before the episode was written). So these days, I’m guessing most viewers assume the show is fake. 

Either way, I’m qualifying it for this list simply because it’s such a funny line that almost comes off as a non sequitur nearly 30 years after Models, Inc. aired.

‘A school with a… website?’

Episode: “You Only Move Twice,” Season 6, Episode 20

Even though the .edu web domain started in 1985, when this episode aired 10 years later, the internet was still a relatively new thing to the general public. If a school had a website (specifically an .edu domain), it was likely a major university, not a local elementary school.

When the Simpsons move to the planned community of Cypress Creek, they find everything is much nicer than Springfield. This includes the Cypress Creek Elementary School, which is so upscale it has (gasp!) its own website: studynet.edu (sadly, unavailable today). 

Fast forward to 2023, and what kind of school wouldn’t have a website? Josh Weinstein, showrunner with Oakley at the time, called it “one of the show’s most obviously dated jokes.” It’s among those special gags that once elicited a laugh, but today’s audiences wouldn’t even realize it was written as a joke.

‘What computers?’

Episode: “Homerpalooza,” Season 7, Episode 24

Now we come to my favorite of all outdated jokes on The Simpsons. Apple Computers was founded in 1976 and had major success during the 1980s with their Macintosh computer, with their peak right around the early 1990s. However, Microsoft began to leave Apple in the dust with its less expensive Windows platform, and Apple was nearing bankruptcy when this episode aired in 1996.

Homer is experiencing a midlife crisis when he’s unable to relate to his kids’ taste in music. When he visits his local music store, he doesn’t recognize any of the bands. He sees a poster of Hullabalooza and declares, “There can only be one truly great music festival a lifetime, and it’s the ‘US Festival.’”

“What festival?” the cashier declares, understandably not recognizing the name of a real two-time festival from the early 1980s that was created by Apple co-founder Steve Wozniak. Homer goes on to explain that “it was sponsored by that guy from Apple Computers.” 

What computers?” the cashier asks, in an absurd punchline but still digging on the presumption that Apple was on its way out. Obviously, the company was able to turn around its business significantly in the decade following, becoming one of the world’s most valuable brands today.

As Homer would say, “The joke’s on you!”

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