The 12 Best Simpsons Guest Stars, Ranked

As with any show that’s been on the air for a while and accumulated a large, dedicated fan base, The Simpsons has attracted some big-name guest stars over the years. As the longest running series in the history of American television, it’s also the series with the all-time biggest number of guest stars.

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Everybody from Mick Jagger to Katy Perry to Danny DeVito to Stephen Hawking has lent their voices to either a one-off character or a yellow, Springfieldian version of themselves. As season 30 brings us even more Simpsons guest stars, here are the 12 best Simpsons guest stars, ranked.

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John Waters in The Simpsons
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12 John Waters as John

John Waters in The Simpsons

The episode “Homer’s Phobia,” in which the Simpson family befriend a gay man named John, much to the chagrin of a narrow-minded Homer, has been praised by LGBTQ rights advocacy groups such as GLAAD for its progressive, inclusive message. John Waters was the perfect casting to play the gay guy who introduces the Simpson family to the gay community because he and his transgressive films thrive in the “campy” side of homosexuality, which is part of what homophobes like Homer are scared of.

The character was designed to resemble Waters, particularly with the thin mustache. The writers even used Waters as a sounding board to determine if the gay community would be offended by anything in the episode, and they took his suggestions on board.

11 Lawrence Tierney as Don Brodka

Don Brodka in The Simpsons

The best episodes of The Simpsons don’t just make you laugh – they also make you feel. “Marge Be Not Proud” is a prime example of that, as Bart is caught shoplifting and tries to hide it from his parents, then tries to make it up to them when they find out.

Reservoir Dogs star and infamous tough guy Lawrence Tierney was the perfect casting to play the store cop who catches Bart in the act. He plays every gag – like the phone call that sounds like a conversation with two sides until he says, “They weren’t home” – in such a deadpan, almost indifferent way that they become even funnier.

10 Peter Frampton as himself

In the season 7 episode “Homerpalooza,” in which Homer attends a music festival called Hullabalooza (a play on Lollapalooza), a lot of musical artists play themselves: the Smashing Pumpkins, Cypress Hill, Sonic Youth. But it’s Peter Frampton who stands out as the funniest because he plays himself as the old guy among all these young new artists.

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For example, he catches Sonic Youth stealing food out of his cooler marked “Property of Peter Frampton” and yells, “Get out of there, you kids!” Sonic Youth’s Thurston Moore says, “Oh, come on, Mr. Frampton. You’re not gonna eat all that watermelon!”

9 Kathleen Turner as Stacy Lovell

The episode “Lisa vs. Malibu Stacy” tackles the sexism of Barbie dolls in the most hilarious and ultimately uplifting way, as Lisa not only points out the outdated, misogynistic lines Malibu Stacy says to the girls she’s brainwashing – she creates her own alternative, Lisa Lionheart.

Kathleen Turner’s low, husky voice was perfect for the cynical, embattled toy mogul who aids Lisa in her quest. Even though, in the end, Malibu Stacy wins out by giving the doll a new hat, the episode’s wider message, carried by Turner, is a feminist one.

8 Patrick Stewart as Number One

“Homer the Great” is one of the best episodes of The Simpsons. In it, Homer discovers a secret society named the Stonecutters, which he is rejected from, only to be let back in when he is found to be “the Chosen One.” Patrick Stewart plays the head of the society, Number One, in one of his first attempts at comedy.

The previously Shakespearean actor made every ridiculous line sound even more ridiculous in his regal, distinguished British accent. Seth MacFarlane and Ricky Gervais clearly took note, as they would take the same joke even further in their own shows in later years.

7 Michelle Pfeiffer as Mindy Simmons

In “The Last Temptation of Homer,” Homer is tempted to have an affair with a new employee at the power plant. She loves donuts, napping, and TV – who does that sound like? Michelle Pfeiffer’s sexy, sultry voice fits the Mindy character so well – she has an irresistible charm that puts us right in Homer’s shoes.

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It also becomes one of the best episodes for Homer and Marge’s marriage as it is tested and ultimately prevails. This is a formula that’s been reused a hundred other Simpsons episodes since, but rarely as effectively as this.

6 Glenn Close as Mona Simpson

While Mona has been brought back a few times with diminishing returns, her debut episode “Mother Simpson” is one of the most hilarious and heartfelt episodes The Simpsons has ever done. Glenn Close turned what could’ve been a forgettable one-off character into someone who feels like she’s always been in the characters’ lives. (The other ones were just retreads – “Mother Simpson” alone would’ve done it.)

She made so much of an impact that when she left, the episode didn’t need anything besides Homer sitting on his car looking up at the stars to convey the emotion.

5 Mark Hamill as himself

Mark Hamill is the first person to make fun of himself and his reputation as Luke Skywalker – just look at his Twitter feed – so he was a prime candidate to make a guest appearance on The Simpsons.

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From lying about having a broken leg to get carried out of a nerd rampage to singing “Luke, be a Jedi tonight!” in a production of Guys and Dolls to using a sci-fi convention appearance to promote Sprint to telling Homer to “use the forks,” every moment featuring Mark Hamill in “Mayored to the Mob” becomes a classic Simpsons moment.

4 Meryl Streep as Jessica Lovejoy

Jessica Lovejoy in The Simpsons

These days, the writers of The Simpsons will lazily set up a premise to bring in a random new character played by a flavor-of-the-month celebrity. But back in its heyday, it would craft episodes of the show that were true to its characters and told a human story, and then cast a big star if the script called for it.

And so goes season 6’s “Bart’s Girlfriend,” in which Bart becomes so infatuated by Reverend Lovejoy’s daughter Jessica that he decides to be well-behaved – only to find that she’s even more evil than him. Meryl Streep plays Jessica’s manipulative machinations so perfectly with her warm, innocent voice.

3 Dustin Hoffman as Mr. Bergstrom

Mr Bergstrom the simpsons

The season 2 episode “Lisa’s Substitute” marks a very important moment in Lisa’s development. Mr. Bergstrom opened the mind of what would become one of the strongest, most empowered female characters in the history of television.

Dustin Hoffman does a great job of both delivering original jokes to make the character stand out on his own (“For the record, there were a few Jewish cowboys, ladies and gentlemen!”) and skewering his own career to show his self-deprecating side (“Mrs. Krabappel, you’re trying to seduce me...”). All in all, Mr. Bergstrom is funny, likable, and had a huge impact on Lisa’s life.

2 Kelsey Grammer as Sideshow Bob

Sideshow Bob Simpsons

While some of Sideshow Bob’s more recent appearances have been lazy cop-outs, going through the same tired formula again and again, there’s no denying that he’s a great Simpsons guest character. And Kelsey Grammer plays the role so well, delivering both the quiet moments of psychotic intellectualism and the maniacal moments of classical villainy with the same level of gusto.

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He even plays the sounds Bob makes when he’s hit in the face with a rake with humility. That grumble says it all: he’s bored of being in the same overused gag yet again, and it really, really hurts.

1 Albert Brooks as various characters

Hank Scorpio in The Simpsons

Albert Brooks has appeared on The Simpsons a few times, always credited as “A. Brooks,” but you wouldn’t know it. Whether he’s playing Homer’s supervillain boss Hank Scorpio in “You Only Move Twice” or the self-help guru Brad Goodman who encourages everyone in town to act like Bart in “Bart’s Inner Child,” Brooks always creates characters that are hilarious, memorable, and most importantly, distinctive from one another.

It’s always his signature hoarse voice, but he always plays a completely different character; Dr. Raufbold and Tab Spangler are worlds apart.

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