The Simpsons: 10 Most Bizarre Celebrity Cameos/Guest Stars

The Simpsons have amassed a large group of fans, made up of millions of weekly viewers. In its 30 years, it has also managed to snag some celebrity guest performances. Some high profile guests like Donald Sutherland, Albert Brooks, Wiliam H. Macy, and others have lent their voice talents to the series.

Other guests have also lent their voices and even likenesses to the show in the absolute most bizarre way. Some do not seem to fit the show, while others feel like they were shoehorned in. Sure, not every cameo fits but at least they provide some memorable moments. These are the ten most bizarre guest stars and cameos on The Simpsons.

10 James Woods

“Who needs the Kwik-E-Mart?” Years before Family Guy, Hercules, Grand Theft Auto: San Andreas or a bunch of racist, sexist and homophobic tweets, James Woods replaced Apu at the Kwik-E-Mart in this fifth season gem, “Homer and Apu.”

In the episode, Apu is driven out of his beloved convenience store for selling expired meat. He is soon replaced by the Videodrome actor, who is supposedly researching for a role. It’s just a weird choice for a cameo and yet another strange instance where The Simpsons did it before Family Guy.

9 50 Cent

“Pranksta Rap” is a pretty weak episode of season sixteen. It acts like an 8 Mile parody that’s come out too late to be relevant. It’s also kind of racist and ignorant of rap and hip-hop culture? The only saving grace of the episode is the “Thursday the 20th” meme.

Anyway, rapper 50 Cent shows up in a phoned-in cameo that feels like every single modern Simpsons cameo. Basically, a Simpsons character will say “oh my it’s [x celebrity and occupation]” and then the guest will reference their own work. It’s a bit tiring.

8 NSYNC

“Word.” This one’s pretty funny. “New Kids on the Blecch” is a twelfth season episode in which Bart, Nelson, Ralph, and Milhouse are featured in a boyband. Unfortunately, they are a proxy to get people to join the navy. The songs in it are absolutely hilarious and catchy and its parody at propaganda is pretty smart.

The NSYNC cameo is also funny, as it features the group giving guidance to the young boyband. Justin Timberlake is excited to meet Milhouse for some reason. The episode ends with NSYNC explaining how great the navy is, defending the United States from Godzilla.

7 Katy Perry

This one is weird because it’s in live-action. For those who don’t remember, Katy Perry was set to appear in an episode of Sesame Street in 2010. Unfortunately, her outfit was deemed “inappropriate” for the children’s program and was cut from the broadcast.

The Simpsons embraced her in the season twenty-two episode “The Fight Before Christmas.” She appeared in a live-action segment where puppet versions of Homer, Bart, Lisa, Marge, Maggie, Moe, and Mr.Burns sing Christmas songs and tell cheesy jokes. It’s a harmless segment that unintentionally parodied a television incident.

6 Gary Coleman

It’s amazing how many cameos Gary Coleman did in his lifetime. Whether it was a Scooby-Doo special or a Drake & Josh episode, he seemed to be anywhere that would pay him. In season eleven episode “The Grift of Magi,” Gary is the security guard at a toy company, though he’s not all in there in the head.

As corny as it is, there are a few good bits in the episode. Gary Coleman’s descent into insanity is pretty funny, as is his argument in the commercialism of Christmas. His final lines, “whatchu talkin’ bout everybody” is an all-time classic Simpsons joke.

5 Ben Stiller

This is the first actor on this list that is playing a character rather than just themselves. Here, Stiller plays the head of a sugar company that Marge issuing. His name is Garth Motherloving and is a parody of supervillains in the funniest way imaginable. He also owns a depressed Oompa Loompa.

Marge eventually loses her goal but audiences are left with one of the best one-off characters ever. At least Homer was able to see a beloved Oompa Loompa. Too bad it was under the direst of circumstances.

4 Thomas Pynchon

Author of Inherent Vice, Gravity’s Rainbow, V, and other novels, Pynchon is known to be a recluse. He rarely gives interviews and nobody ever knows where he is.

Apparently, he was too busy doing guest spots on The Simpsons. Here, Pynchon plays himself on two separate occasions. Both times, he is wearing a bag over his head and making it very obvious who he is. He has joined authors like Tom Clancy, Maya Angelou, and Stephen King as guests on this show. Hopefully, others can be lucky enough to meet Pynchon one day.

3 Matt Groening

Creator of Futurama’s own Bender, Matt Groening’s name appears all over The Simpsons’ marketing material and credits. In the episode “My Big Fat Geek Wedding,” he can be seen at a Springfield science-fiction convention.

Playing himself, he greets fans enthusiastically (and incredibly sarcastically) and says he will sign autographs anywhere and anytime. He mentions that fans can ask on the street, his private property, request a sketch or a lock of his hair. It’s this passive-aggressiveness that makes it so funny and really zeroes in on what makes fandom so scary for a lot of artists.

2 Jon Lovitz

No, this does not include Artie Ziff, the slimy former flame of Marge Simpson. This is Jon Lovitz as Jay Sherman, the critic on, well The Critic. ABC’s animated series was moving to FOX, so there was this big push to do a crossover. While the episode “A Star is Burns” is not that bad, Sherman’s appearance can’t help but feel a little bit forced.

Lovitz is a wonderful performer and one of the funniest people alive. Sherman is also an all-time great animated character but maybe The Simpsons isn’t the best place for him?

1 Jim Jarmusch

This cameo stems from Homer not knowing who this is. Filmmaker Jim Jarmusch is one of the coolest directors around, making classics like Down By Law, Ghost Dog, and Stranger Than Paradise. He’s not necessarily the most mainstream director, so him appearing on an episode of one of the biggest shows ever, seems kind of wrong? He makes references to his films and does the same thing other Simpsons cameos do. It’s such a bizarre guest spot for one of the most underground auteurs.

At least it’s funny and I’m sure Jim Jarmusch’s Cheaper By The Dozen 3 would be a masterpiece.

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