8 The Simpsons Celebrity Guest Stars That Aged Poorly

“The Simpsons” writers may have predicted some pretty improbably future events, but even they couldn’t have anticipated some guest appearances that didn’t just age poorly, but festered within the cracks of one of the most essential and influential television shows ever made. Throughout its 36 seasons, 781 episodes, and one feature-length film, there have been notable guest star appearances that may have been hilarious at the time, but became anything but.  

In addition to the various “Simpsons” jokes that have aged poorly, some cameos have become truly uncomfortable, and now land with all the comedic impact of a fingernail extraction. After reviewing the series, here are the worst cameos in the show’s history. These appearances remind us that convicted felons, despised public figures, and unsuccessful sports icons alike have made a stop in Springfield, hoping for a memorable visit that ultimately became forever tainted due to real-life events. In some cases, where a “D’oh!” or an “Ay Carumba!” really didn’t quite cut it, celebrity appearances were removed entirely.

Though Dan Castellaneta voiced Cosby during his appearances in “The Simpsons,” this doesn’t change the fact that, real deal or not, any television program referencing Bill Cosby creates a wince-inducing experience we’d rather forget. Throughout the series, “The Simpsons” made several references to Cosby before 2014, when multiple sexual assault charges were brought against the comedian, leading to a prison sentence and more women coming forward after his release. 

The final reference to Bill Cosby on “The Simpsons” was cut from an episode in 2018 following the announcement of Cosby’s assault and sentencing. It wasn’t until 2023 that the show returned to jab at Cosby with upgraded material in season 34, episode 14, “Carl Carlson Rides Again.” In a brief joke featuring Dr. Hibbert, Springfield’s esteemed physician is seen trying to sell some sweaters that have the same signature look as Cosby’s old knitwear, only to be informed by a thrift store sign that they are “no longer accepting Cosby sweaters.” It’s a fitting dig at a now-ruined career, embodying the right level of humor for which “The Simpsons” is known. It’s just a great shame that the joke could even be made in the first place.

While it might be a relatively old cameo now, the issue surrounding it is undoubtedly one of the show’s rawest. Author Neil Gaiman played himself in “The Simpsons” season 23, episode 6, “The Book Job” in 2011. The episode saw Homer and Bart working on their own fantasy novel, which led to a run-in with the writer of “The Sandman” and “Coraline” who, since 2024, has been accused of sexual assault by eight different women. Currently, the author has multiple projects being adapted from his works, including “The Sandman” and the final chapter of “Good Omens” (which, according to Deadline, went from a series to a feature film following the allegations). Disney’s plans for “The Graveyard Book” have been put on hold as well (as per IndieWire). With that in mind, it already has fans asking if his appearance in the beloved sitcom will get the same treatment.

At the time of writing, the episode is still available to watch on Disney+ with Gaiman, even on the episode’s cover image, but fans are still questioning if will be taken off in due course. Over on X, @Garebear__11 asked, “How long until that Neil Gaiman episode of The Simpsons gets pulled from streaming and the only way to ever see it is if you own the DVD?” Who knows if this will come to pass, but for now, it’s one of many episodes on the show that for some, might be worth skipping.

In an episode that has aged like milk funneled from the wasteland of “Mad Max,” the first episode of “The Simpsons” season 11, “Beyond Blunderdome,” saw Homer befriend Mel Gibson and become a consultant for the Oscar-winning star for his next project. Comedy ensues as Homer’s efforts to mold what he thinks would be a good film for Gibson backfire dramatically, and the partnership ends before the credits roll. It’s the episode that gave us that gif of the dog with shifty eyes, but its main guest star has a much less enjoyable legacy. Seven years later after it first aired, Gibson would be arrested for a DUI and, in the years that followed, was caught going into antisemitic, racist, and homophobic tirades.

While he has gone on to both star in and direct films, there’s no question that Gibson’s career isn’t what it used to be and has only fallen further in the last few years. Just recently, the “Braveheart” director caught some heat after denying climate change and the theory of evolution in an appearance on “The Joe Rogan Experience.” In “Beyond Blunderdome,” anyone and everyone in Springfield was a fan of Mel Gibson. Now, it’s a lot harder to find someone who is.

For better or worse, the Simpsons’ innate ability to predict the future hit a real nerve in the case of MLB star and Cardinals batter Mark McGwire. In the 1999 episode “Brother’s Little Helper,” Bart believes Major League Baseball is monitoring Springfield. His terrible theory is proven true when McGwire makes a guest appearance, dropping in via helicopter and rocking the youngster’s world by telling him he’s right. What makes this particularly wild is that 16 years later, the Cardinals would get caught up in a hacking scandal that needed more than a few dingers to shift the attention.

Following an investigation in 2015, it was revealed that the St. Louis Cardinals hacked into the Houston Astros’ team database to gain an advantage over the opposition. Scouting Director Chris Correa was confirmed to be responsible, resulting in the Cardinals paying the Astros $2 million and losing two of their draft pick choices. As far as predictions from Springfield’s finest go, this one is wildly specific and, while perhaps the least impactful, might leave some Cardinals fans to this day doing a Simpsons collar-pull at the joke that didn’t turn out to be funny over a decade down the line.

When actor James Woods started to speak out with some highly sensitive political and sexist views, his animated iteration in “Family Guy” was seemingly wiped from Quahog completely. The show even changed the name of James Woods High School to Adam West High School, in memory of the late “Batman” star and Quahog mayor. “The Simpsons” hasn’t been so quick on the mark, perhaps because Woods only appeared in one episode of the show. Still, it certainly doesn’t make for a fun watch anymore.

The episode “Homer and Apu” sees the titular pair head to India so Apu can get his job back after Homer blows the whistle on the Kwik-E-Mart owner selling expired meat. During their trip, Woods steps in as Apu’s replacement and provides discomfitingly intense service during his time there. Like many other episodes on this list, Woods’ presence feels like just one more star who’s seen in a very different light now and is just another chapter in the show’s long-running history that can be skipped over entirely. Admittedly, the Kwik-E-Mart’s usual proprietor, Apu, has also aged poorly and is in a lot more episodes. White voice artist Hank Azaria had voiced the Asian character since 1990, but rightfully stepped down from the role in 2020.

Initially considered one of the greats, “Stark Raving Dad” sees Homer sent to a mental institution after wearing a pink shirt to work and ends up in a room with Michael Jackson. Well, not the Michael Jackson, but a man who believes himself to be. This creates a comedy of errors as Homer brings his roommate (whose real name is Leon Kompowsky) home and squashes Bart and Lisa’s dreams that the King of Pop is coming to their house. The voice of Leon was credited as John Jay Smith and his true identity was a mystery for years. It wasn’t until 2018 that Matt Groening confirmed Michael Jackson himself had voiced Leon.

The enjoyment from the revelation was short-lived, though. A year later, and following the release of the documentary “Leaving Neverland,” which shone a spotlight on the alleged sexual abuse of young boys by the musician, the episode was pulled off the air and has remained as such ever since. Discussing the reasons behind the decision (via The Daily Beast), showrunner Al Jean expressed concerns that Jackson had weaponized the episode to prey on his alleged victims. “I think it was part of what he used to groom boys,” Jean said. “I really don’t know, and I should be very careful because this is not something I know personally, but as far as what I think, that’s what I think. And that makes me very, very sad.”

What do “Dodgeball” and “The Simpsons” have in common? They both have a cameo from a sports star who is now banned from performing in the thing that made his career. In season 19, episode 19, entitled “Mona Leaves-a,” Homer gets a visit from his estranged mother, Mona, played by Glenn Close. The episode is all about Mona’s final reunion with her son before she passes away, leaving Homer to complete a bucket list of sorts in her memory. It’s a heartfelt entry, but rewatches are slightly derailed by a brief appearance from former cyclist Lance Armstrong, who is seen on television giving an ESPY award with Fozzie Bear. 

Thankfully, both Close and Fozzie Bear escape the episode unscathed, as Armstrong’s appearance is a blink-and-you’ll-miss-it gig. Airing in 2008, it would be another four years before the then seven-time Tour de France winner was stripped of his titles and achievements and stamped with a lifetime ban from racing for illegal doping. While it’s perhaps not as prominent as other appearances in the show, it’s still a surprise that makes you realize just how often “The Simpsons” feels like a product out of time, with the famous names of that era to match it.

The Elon Musk-starring installment of “The Simpsons” was unfunny enough to begin with, but it has only gotten worse with age thanks to the fake-news-funneling tech billionaire’s presence in just about every area we’d prefer him not to be. However, given how he’s perceived in season 26, episode 12 — “The Musk Who Fell to Earth” — you wouldn’t think that was the case. The episode sees Musk visit Springfield and suggest to Mr. Burns that building another power plant would be a great idea. It isn’t, and as a result, old Monty B goes about getting his revenge on Musk for the failed venture. 

Earning terrible reviews following its initial release, the Musk-based episode of the beloved series is about as funny as you’d expect if you’ve ever seen the X/Tesla owner jumping around on a podium. The Guardian deemed it “the most fawning episode” of a series with incredible A-listers over the years, delivering what feels like a Z-lister we’d rather forget. It’s some 20 minutes dedicated to trying to sell just how great Musk is when the last decade has proven that to be not the case. Between this, “Iron Man 2” and social media platforms, Musk really makes it so we can’t have nice things.