The ‘Simpsons’ Jokes That Aged the Worst

Fans pick the most dated punchlines and dusty gags in ‘Simpsons’ history
The ‘Simpsons’ Jokes That Aged the Worst

For all the major world events that Matt Groening and The Simpsons have successfully predicted during their 34-year run on TV, they really whiffed on the World Trade Center.

The Simpsons began in the first year of George H.W. Bush’s presidency and has continued well past his passing. In that time, trends have come and gone, krumping happened and celebrities have turned from beloved to reviled and vice versa. Times have changed since The Tracey Ullman Show first unleashed America’s favorite nuclear family upon the world, and, for as many classic Simpsons jokes have aged like a fine antifreeze-free wine, just as many have aged like curdled malk.

Over in the Simpsons subreddit, the superfans recently discussed which Simpsons jokes were a hell of a lot funnier before we knew what Jared from Subway was really up to. Here are their top picks…

Cypress Creek Elementary Schools Website

The obligatory pick for poorly aged Simpsons jokes goes to the URL on the sign of the Simpsons childrens new elementary school in “You Only Move Twice.” Prolific Simpsons writer Josh Weinstein has gone on record saying that this is the most dated joke of the Simpsons Golden Age because, within a decade, an elementary school having a website would be positively mundane phenomenon. “Nobody ever says Italy,” however, is as timeless as France itself.

“Aw, the Denver Broncos!”

To be fair, Homer’s famous football complaint at the end of 1996’s “You Only Move Twice” (yep, that episode again) goes in and out of relevance depending how Denver’s squad is performing — the Broncos would go on to win back-to-back Super Bowls in 1998 and 1999. Nowadays, the Sean Payton/Russell Wilson experiment isn’t paying any dividends, and the Dallas Cowboys are still the more attractive team to own for anyone who understands football — unlike Marge.

“I’m Jared From the Subway Ads! I’m Only A Little Overweight and Sexually Ambiguous”

If only “ambiguous” was the worst way to describe Jared Fogles sexuality. When Chief Wiggum donned the now-notorious pedophiles iconic extra-large pants in “Treehouse of Horror XVI” back in 2005, he had no way of knowing that they belonged to yet another horrible criminal who Springfields most inept police chief failed to sniff out.

“Robert Downey Jr. Is Shooting It Out With the Police!”

Everyone in 2023 knows Iron Man to be Hollywood’s greatest comeback story, but in 1999, Robert Downey Jr. was just an embattled nepo baby who flamed out of Saturday Night Live before being a B-grade heartthrob. The same year The Simpsons skewered him in “Beyond Blunderdome,” Downey Jr. famously told a judge, “It’s like I have a shotgun in my mouth, and I’ve got my finger on the trigger, and I like the taste of the gun metal.” Today, he prefers the taste of shawarma.

“They Stick All the Jerks in Tower 1”

“The City of New York vs. Homer Simpson” left syndication for half a year after 9/11, and Homers parking quandary seemed lost to the airwaves forever. When the episode did finally return to television in 2006, the marvelously New York confrontation between Towers One and Two was cut from the broadcast, but that didnt stop us from thinking spectacularly poor taste jokes about never forgetting it.

“The Bartender Even Looks Like John Travolta!”

Just 12 days before John Travolta sparked the Travoltaissance with an appearance in Pulp Fiction, he tended bar at Itchy & Scratchy Land, making this poorly-aged Simpsons joke the quickest to reach its expiration date. When the episode aired, Travolta was a washed-up has-been who had gone the way of disco — days later, he was boogying through movie history with Uma Thurman.

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