The 5 Worst Simpsons Cameos, Ranked

"The Simpsons" surely has one the most impressive lists of guest stars in all of TV history. Everyone from Michael Jackson to Elizabeth Taylor have appeared on the long-running series, which quickly became a cultural institution capable of attracting seemingly any public figure from any sphere of life.

Celebrities agreed to appear on "The Simpsons" with little hesitation, but the show has also hosted musicians, authors, politicians, and even prominent scientists such as Stephen Hawking. Often, as was the case with Hawking, these guest appearances make for some of the show's best moments, with the late physicist managing to get into a physical altercation with Principal Skinner before revealing his chair comes with a propeller that allows him to airlift himself out of danger.

But with "The Simpsons" now having run for 36 seasons, you're bound to have some duds among the plentiful cameos. With that in mind, here are the five worst guest-stars to have ever appeared on the show.

While many "Simpsons" episodes give guest stars an entire storyline, often the show only manages to secure a brief cameo. That was the case with season 16 episode "Pranksta Rap," a good example of how, by that point, the show really had lost its way. Debuting in 2005, this rap-focused episode seemed about a decade too late to be relevant. Despite the fact that "8 Mile" had been released just three years prior, the show's attempt to parody the Eminem-led drama simply felt like a good way to advertise how behind the times the series was.

Sadly, even a guest appearance by Curtis "50 Cent" Jackson couldn't do much to save this installment from itself. The rapper is in the episode for less than 20 seconds, pulling up alongside Bart in his stretch Hummer and offering him a spot on his world tour. There's nothing egregious about 50's line delivery, but he's such a small part of the episode it feels like a missed opportunity. A joke about him having to carry out community service at the local park also falls flat, making for one of the most underwhelming cameos in "Simpsons" history.

Another guest appearance that's too brief to really bring much to the show, Mark Zuckerberg showed up in 2010 episode "Loan-a Lisa," part of season 22, which certainly won't be cropping up on any lists of the best "Simpsons" seasons. The story sees Lisa trying to convince Nelson not to dropout of school, leading the pair to attend an entrepreneurs' convention where they meet Zuckerberg.

The tech mogul doesn't really do much beyond advising Nelson that drop-outs like himself can become successful. The only real joke revolves around Zuck constantly updating his Facebook page with statuses such as "Mark Zuckerberg is happy to meet new friends," and later after he's tripped at a roller rink, "Mark Zuckerberg is in intense pain." Neither jokes really land, making for a cameo that, much like 50 Cent's brief appearance, just sort of comes and goes.

It also feels like a big missed opportunity for the show, which in its sharper years surely could have made a real meal out of taking Zuck and his tech overlord persona down a few pegs. As it stands, this just feels like the writers were relying on the novelty of getting the dude who made Facebook.

There was a time when "The Simpsons" was one of the most insightfully satirical shows on TV. Though its premise revolved around sending up the idea of the typical American family, it really functioned as a send-up of American culture as a whole, taking aim at everything from politics to pop culture and finding a hilarious and clever way to point out the absurdity of it all. It was truly subversive, and had comedy as its guiding principle.

Since those early years, "The Simpsons" has been swallowed up by Disney following its merger with Fox, but in truth had already lost almost all of its subversive power by that point. Case in point: the 2012 episode "Lisa Goes Gaga." This season 23 installment at least gave guest star Lady Gaga more to do than 50 Cent, but that essentially equated to what felt like a commercial for the pop star and her growing base of "Little Monsters."

The episode sees Gaga visit Springfield to lift the town out of the doldrums for some reason, and Lisa being the most depressed resident gets special attention from the singer. By the end, Lisa embraces the Gaga spirit, essentially becoming one of the pop star's monsters and singing an entire musical number. The idea is that Lisa regains some sense of who she is and what makes her special, which in and of itself isn't a bad idea. But compare this kind of thing to such classics as "Lisa's Substitute." That season two installment accomplishes the same thing as "Lisa Goes Gaga" in a much more moving and understated way by having Dustin Hoffman's Mr. Bergstrom give the precocious youngster a simple, life-affirming note that states, "You are Lisa Simpson." As such, Gaga's guest spot really does seem like a needlessly gaudy, hollow, and commercial affair. Oh, and at one point, Gaga kisses Marge, so there's also that.

Katy Perry was on "The Simpsons" and we could probably end this section here. But if you must know more details, the singer appeared in 2010's "The Fight Before Christmas," in a rare live-action segment that saw her talking to puppet versions of the Simpsons family.

The Christmas-themed episode is structured around four dream segments, with Perry showing up in Maggie's vision of "A Fluppet Christmas Special." The segment, which emulates the look of "The Muppet Show" and "Sesame Street," sees Moe housesit the Simpsons' abode while the family go on vacation. Then Perry shows up for some reason. Why the whole "Muppet"/"Sesame Street" thing? Well, apparently Perry was set to appear on the latter but had her segment cut due to it being deemed too risqué. While it has been claimed that her "Simpsons" appearance was designed to make up for that debacle, as Entertainment Weekly pointed out at the time, her appearance was shot before all the controversy arose. So, it seems her "Simpsons" guest role was actually simply inspired by the fact she was set to appear alongside Elmo and the gang, and not her removal from the final cut.

Either way, Perry's guest spot didn't really do much to make up for anything. The only real gag is that she's supposed to be Moe's girlfriend and that's pretty much it. The only thing more disappointing is the way in which this entire segment, though designed as a parody of Jim Henson's puppet shows, advertises the complete lack of any subversive spirit in a show that once represented the apex of satirical TV. By the time the whole family, accompanied by Perry, break out into a rendition of "The 39 Days of Christmas" at Mr. Burns' behest, the urge to just cancel Christmas altogether has become overwhelming.

Remember when Elon Musk carried that sink into Twitter HQ and thought it was hilarious as a literal representation of the already tiresome buzz-phrase, "Let that sink in" (after which he fired a bunch of people)? Or when he got into a fight on Twitter/x with a satirical video game website over a meme, then got roasted for his appearance on "Saturday Night Live," during which we now know he made the great Chloe Fineman cry? It seems that for Elon, being the world's richest man with an inordinate amount of global influence is not enough. He simply must be seen as the funny guy, too. Lamentably, nothing he's done thus far has indicated that he's worthy of any such designation, including that time he guest-starred on "The Simpsons."

"The Musk Who Fell To Earth" was already doomed simply by virtue of the fact it belonged to late-stage "Simpsons," which despite some impassioned arguments to the contrary, is pretty dire stuff. This 2015 episode actually puts Musk center-stage, which ... why? The man's blunt and lifeless line readings do nothing to help his case for being some sort of comedic mastermind (he apparently repeatedly told Fineman that her writing was unfunny and therefore not fit for his "SNL" appearance), and don't even seem befitting of the goofy little internet prankster image he presents online. It's exactly this sort of thing that leads prominent outlets such as Rolling Stone to form a grand unified theory of why Elon Musk is so unfunny.

As the episode goes on, nothing really changes in that respect. Musk is monotone throughout, and the story surrounding him doesn't do much to help things. But this episode did air during a time when Musk's online notoriety was nowhere near where it is in 2024, so we can't really blame "The Simpsons" itself for trying to build an episode around a man who was yet to reveal just how unfunny he really was. Instead, let's blame that man himself.