The Simpsons’ Best Guest Stars
For a small town, Springfield sure attracts a lot of famous people. The Simpsons has welcomed celebrity guest stars since the very first season, and they’ve never slowed down. In 34 years, they’ve amassed a lot of gems. Here are some of the best.
1. Tony Hawk
The world’s most famous skateboarder had the privilege of helping The Simpsons ring in their 300th episode of “Barting Over.” Regular skateboarding wasn’t enough for such a momentous occasion, so the show treated us to a superpowered skateboarding duel to the death between Homer and Tony Hawk.
2. Jon Lovitz (Various)
Lovitz stands in an exclusive circle of guest stars who have graced the show with multiple characters. For some reason, most of his roles revolve around Marge. He’s played her billionaire prom date (Artie Ziff), her theater director (Llewellyn Sinclair), and her art teacher (Professor Lombardo). In a crossover episode, he played Jay Sherman from The Critic to help Marge throw a film festival for Springfield.
3. Danny Devito (Herb Powell)
Homer having a secret half-brother: surprising! Homer ruining his life? Much less so. Homer and Herb welcomed each other with open arms, but the relationship soured when Homer’s car design drove Herb’s company out of business. Danny Devito’s performance perfectly balanced melodrama and comedy.
4. Rodney Dangerfield (Larry Burns)
Rodney Dangerfield got no respect, but at least he got a guest spot on The Simpsons. He plays Larry, the long-lost son of Mr. Burns. While he and Homer hit it off instantly, he couldn’t connect with his billionaire dad. It took a fake hostage situation to stitch the relationship back together.
5. Phil Hartman (Various)
The late Phil Hartman held a place on The Simpsons that could never be replaced. He brought to life fan-favorite recurring characters Lionel Hutz, Troy McClure, and one-time villain Lyle Lanley. His comedic presence elevated every episode in which he appeared.
6. Kelsey Grammer (Sideshow Bob)
Sideshow Bob has been with The Simpsons since the inaugural season, and she hows no signs of disappearing anytime soon. Kelsey Grammer delivered a performance so iconic it’s no wonder the show kept bringing him back. A bonus mention goes to David Hyde Pierce, who plays Sideshow Bob’s brother, Cecil, a clever nod to Grammer and Pierce playing the brothers Frasier and Niles Crane on Frasier.
7. Sting
The Police frontman can’t rest when one of his fans is in danger. After repairing his relationship with Krusty the Clown, he leads a parody of “We Are the World” to save the imaginary child Bart tricked everyone into thinking he got stuck in a well. When Bart did get stuck in a well, Sting dug without rest until Bart was rescued.
8. Leonard Nimoy
Leonard Nimoy’s performance in “Marge vs. the Monorail” helped secure the episode as the best of all time in many fans’ minds. He saved Krusty’s life and made a man very uncomfortable by talking about the cosmic ballet. Once his work was done, he teleported away before our very eyes.
9. Mark Hamill
Mark Hamill took a break from being the best Joker voice actor to give The Simpsons some love. Anyone with the secret dream of saving Luke Skywalker’s life got to live it vicariously through Homer as he fought his way through crowds of nerds to bring Mark Hamill to safety.
10. Conan O’Brien
“Bart Gets Famous” gave Conan O’Brien the honor of having both been in the writing room for The Simpsons and being on the show. Bart wants to prove that he’s more than just a dumb catchphrase, but Conan’s having none of it and callously makes Bart say his line. Remember, only Conan may dance.
11. James Woods
Of all the things a show could do with a big-shot Hollywood guest star, sticking him behind a convenience store counter isn’t the first thing that comes to mind, but The Simpsons pulled it off. James Woods takes his research very seriously, so we see him live the life of a Kwik-E-Mart clerk. Until he had to leave and battle aliens on a faraway planet, that is.
12. Buzz Aldrin
Only The Simpsons could take a man with one of the most monumental accomplishments in human history and get him to say, “Careful! They’re ruffled!” Buzz Aldrin has been on the moon and on The Simpsons, which accounts for living the dreams of just about every American.
13. Every Musical Act in “Homerpalooza”
Every player in “Homerpalooza” does such a great job that it would be criminal to pick just one: Sonic Youth raided Peter Frampton’s cooler, Cypress Hill ordered an orchestral version of “Insane in the Membrane,” Billy Corgan served up Homer’s “smiling politely” line, and Peter Frampton gets frustrated by it all.
14. Johnny Cash (Coyote)
Sometimes, celebrities voice themselves. Other times, they voice an original character. But on extra rare occasions, they voice mystical talking foxes that only exist in hot pepper-induced hallucinations. Johnny Cash kills it as the fox who serves as Homer’s spiritual guide in “The Mysterious Voyage of Our Homer.”
15. John Waters (John)
It may seem quaint now, but “Homer’s Phobia” broke new ground for an episode. John Waters stars as John (a different John, not himself) in an episode where Homer must confront his bigoted views on gay people. John Waters gives a delightful performance as the owner of a vintage collectibles shop who befriends the Simpsons.
16. Stephen Hawking
Even someone as brilliant as the late theoretical physicist Stephen Hawking can be a fan of The Simpsons. When he isn't explaining the physics of black holes localized in a hardware store, he's having a drink at Moe's and punching Homer with his chair's built-in boxing glove.
17. Gary Coleman
The late Gary Coleman showed us how powerful catchphrases can be in “Grift of the Magi.” He plays himself as an enthusiastic but unobservant security guard working for Lindsay Naegel. He does so much in such little time to guarantee a spot on this list.
18. Jane Kaczmarek (Judge Harm)
Corporate synergy can lead to some crossover duds, but bringing in one of the stars of fellow Fox hit Malcolm in the Middle beat the odds. Kaczmarek did such an excellent job of bringing her Lois energy to The Simpsons that Judge Harm has made the occasional appearance even 20 years after her debut.
19. Stan Lee
A surprise visit from Stan Lee made Comic Book Man learn the lesson “never meet your heroes” the hard way. At first, he was starstruck by the comic legend visiting his shop, but by the end of the episode, he couldn’t wait until this crossover event ended.
20. Adam West
Believe it or not, there was a time when Adam West was mostly confined to cartoon cameos. Johnny Bravo, Family Guy, and Fairly Oddparents all had their turn, but The Simpsons did it best. It's too bad we never found out why Batman doesn’t dance anymore.
21. Weird Al
If a cartoon doesn’t have a Weird Al guest appearance, is it even a good show? Weird Al starred as himself to save Homer and Marge’s marriage with a parody of John Mellencamp’s “Jack & Diane.” Years later, he returned to turn Homer’s grunge anthem “Shave Me” into “Brain Freeze.”
22. JK Simmons
J.K. Simmons gave such an iconic performance as Spider-Man character J. Jonah Jameson that the character followed him into animation. He’s appeared multiple times as a JJJ existing in The Simpsons’ world, the best one being when he runs a poetry journal and demands poems about Spider-Man. But because Simmons has more than just one hit, in Season 30, the show treats viewers to him playing a parody of his character Terence Fletcher from Whiplash.
