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Celebrity Cameos on The Simpsons: Ranked from Worst to Best

12 min read

Over 35 seasons, The Simpsons has attracted Hollywood's biggest stars, music legends, and even presidents. Some elevated their episodes to classic status. Others... well, let's just say not everyone can pull off yellow skin. Here's our definitive ranking of celebrity cameos, from the forgettable to the absolutely legendary.

The Worst: When Star Power Fizzles

15. Lady Gaga (Season 23, "Lisa Goes Gaga")

The Role: Herself, arriving in Springfield to cheer up Lisa
Why It Didn't Work: Even Simpsons writers have apologized for this one. Gaga's over-the-top positivity felt forced, the songs were forgettable, and the whole episode felt like a 22-minute commercial. When your cameo makes longtime fans question the show's integrity, you've missed the mark.

14. Elon Musk (Season 26, "The Musk Who Fell to Earth")

The Role: Himself, becoming Homer's friend
Why It Didn't Work: The episode aged like milk in a Tesla trunk. Musk's wooden delivery and the fawning portrayal of him as a genius inventor feels cringey in retrospect. The Simpsons works best when it mocks powerful people, not when it kisses their rings.

13. Mark Zuckerberg (Season 23, "Loan-a-Lisa")

The Role: Himself, giving entrepreneurial advice
Why It Didn't Work: A billionaire telling kids to drop out of school? The tone-deaf message combined with Zuckerberg's robotic delivery created one of the most skippable cameos in Simpsons history. Even his animated avatar seemed uncomfortable.

The Mediocre Middle: Star Power Without Sparkle

12. Katy Perry (Season 22, "The Fight Before Christmas")

The Role: Moe's girlfriend in a live-action segment
Why It Didn't Work: The live-action/puppet segment was already weird, and Perry's appearance as Moe's girlfriend felt more like stunt casting than clever writing. Points for trying something different, but it landed with a thud.

11. Tony Blair (Season 15, "The Regina Monologues")

The Role: Himself, welcoming the Simpsons to the UK
Why It Didn't Work: Political cameos age poorly, and Blair's appearance feels especially awkward now. The jokes were safe, the delivery was stiff, and the whole thing felt like a diplomatic obligation rather than comedy.

10. Alec Baldwin & Kim Basinger (Season 10, "When You Dish Upon a Star")

The Role: Themselves, befriending Homer
Why It Didn't Work: Not terrible, just forgettable. The episode mocked celebrity culture effectively, but Baldwin and Basinger didn't add much beyond their names. Their divorce shortly after made rewatching uncomfortable.

The Good: Celebrities Who Got The Assignment

9. Paul & Linda McCartney (Season 7, "Lisa the Vegetarian")

The Role: Themselves, teaching Lisa about vegetarianism
Why It Worked: The McCartneys brought genuine warmth to their roles, and their appearance actually served the plot. "Maybe I'm Amazed" playing over the credits remains a beautiful moment. They even insisted Lisa stay vegetarian permanently—the only time a guest has changed canon.

8. Stephen Hawking (Multiple Episodes)

The Role: Himself, usually outsmarting everyone
Why It Worked: Hawking got the show's humor and delivered self-deprecating jokes with perfect timing. His wheelchair with a built-in helicopter and boxing glove became iconic. He loved the show so much he came back four times.

7. Johnny Cash (Season 8, "El Viaje Misterioso de Nuestro Jomer")

The Role: The Space Coyote
Why It Worked: Cash's gravelly voice as Homer's spirit guide was perfect casting. Mysterious, profound, and slightly menacing, he elevated a trippy episode into something genuinely spiritual. "Find your soulmate, Homer."

The Great: When Celebrities Become Springfield Legends

6. Danny DeVito (Season 5, "Homer's Triple Bypass")

The Role: Herb Powell, Homer's half-brother
Why It Worked: DeVito didn't just do a cameo—he created a fully realized character. Herb felt like he belonged in the Simpsons universe, and DeVito's energy matched the show perfectly. So good he came back for another episode.

5. Michael Jackson (Season 3, "Stark Raving Dad")

The Role: Leon Kompowsky, a mental patient who thinks he's Michael Jackson
Why It Worked: Despite later controversies leading to the episode being pulled, this was masterful celebrity cameo work. "MJ" helped Bart write "Happy Birthday Lisa," creating one of the show's most touching moments. The mystery around his involvement only added to the legend.

4. Dustin Hoffman (Season 2, "Lisa's Substitute")

The Role: Mr. Bergstrom, Lisa's substitute teacher
Why It Worked: Credited as "Sam Etic," Hoffman brought genuine emotion to one of the series' most heartfelt episodes. His chemistry with Lisa was perfect, and "You are Lisa Simpson" remains one of the show's most touching moments.

The Legendary: Cameos That Defined The Simpsons

3. Leonard Nimoy (Multiple Episodes)

The Role: Himself, narrating alien encounters
Why It Worked: Nimoy understood the assignment completely. His deadpan delivery of absurd lines ("A solar eclipse. The cosmic ballet goes on.") was comedy gold. He embraced the silliness while maintaining his dignity. "May the force be with you!" "Do you even know who I am?" "I think I do. Weren't you in Star Wars?"

2. Kelsey Grammer (Multiple Episodes)

The Role: Sideshow Bob
Why It Worked: Grammer transformed a one-note villain into one of TV's greatest recurring characters. His theatrical delivery, singing voice, and ability to make Bob simultaneously menacing and ridiculous created magic. The rake scene alone justifies this ranking. "Die, Bart, Die" becoming "The Bart, The" in German? Genius.

1. Phil Hartman (Multiple Episodes)

The Role: Troy McClure, Lionel Hutz, and others
Why It Worked: Hartman wasn't just a guest—he was family. His characters became so integral to Springfield that the show retired them after his death rather than recast. "Hi, I'm Troy McClure. You may remember me from..." became one of the show's most beloved running gags. No celebrity understood The Simpsons' tone better or contributed more to its golden age.

The Secret to a Great Simpsons Cameo

The best cameos understood a crucial truth: The Simpsons works when celebrities are willing to be mocked, show humility, or disappear into a character. The worst cameos treated the show as a promotional opportunity or demanded reverence.

It's the difference between Phil Hartman creating timeless characters and Lady Gaga using Springfield as a concert venue. Between Leonard Nimoy joking about Star Wars and Elon Musk wanting to look cool.

Want Your Own Celebrity Moment?

While you might not get animated by the actual Simpsons team, you can still experience the magic of seeing yourself transformed into a Springfield resident. Turn yourself into a Simpsons character instantly at simpsonify.ai—no agent, no studio contract, no wooden line delivery required.

Who knows? Your Simpsonified portrait might be more memorable than some of these actual celebrity cameos. At least you won't end up on anyone's "worst" list.

"Hi, I'm Troy McClure. You may remember me from such websites as simpsonify.ai and other quality internet destinations!"