THERE HAVE BEEN hundreds of celebrity cameos during The Simpsons’ 25-year run (just look at the length of this list), each as delightful as the last. 

But by far the most intriguing cameos occur when celebrities play entirely new characters, and not just Simpson-ified versions of themselves.

Here are 11 of the most surprising celebrity cameos, from Meryl Streep to Benedict Cumberbatch and everyone in between.

Meryl Streep as Jessica Lovejoy

Episode: “Bart’s Girlfriend”, 1994

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Meryl appeared on The Simpsons back in 1994, sounding absolutely nothing like herself as Reverend Lovejoy’s sweet-and-innocent daughter, Jessica.

Bart falls head over heels in love but Jessica quickly reveals herself to be evil and manipulative, memorably calling him “yellow trash”. Boo.

Elizabeth Taylor as Maggie Simpson

Episode: “Lisa’s First Word”, 1992

Trust The Simpsons to snag a massive guest star like Elizabeth Taylor, then use her for just one word: “Daddy.”

Perfect.

Dustin Hoffman as Mr Bergstrom

Episode: “Lisa’s Substitute”, 1991

Dustin Hoffman was one of the show’s first big celebrity cameos, playing Lisa’s enthusiastic substitute teacher Mr Bergstrom way back in 1991.

Though he worked under the pseudonym Sam Etic, the episode dropped a rather large hint as to who the real actor might be:

Mr Bergstrom was the teacher of Lisa’s dreams, and she was devastated when it was time for him to leave again. But who didn’t sigh happily at his life-affirming note to Lisa at the end of the episode?

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Michael Jackson as Leon Kompowsky

Episode: “Stark Raving Dad”, 1992

Jackson called up Matt Groenig looking for a part on the show and even composed Happy Birthday Lisa, but had a few conditions: he insisted on doing only Kompowsky’s speaking voice, wanted a sound-alike to sing for him, and wished to be credited as John Jay Smith. Confusing

They couldn’t complain too much though, as Jackson later helped write Bart Simpson’s hugely popular single, Do The Bartman. Sound.

Winona Ryder as Allison Taylor

Episode: “Lisa’s Rival”, 1994

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The teen movie queen was still at the peak of her powers when she played a new Springfield Elementary student, Allison Taylor, who threatens to topple Lisa from her perch as the school’s smartest student.

We will love this episode forever for giving us ‘Diorama-rama’.

Mandy Patinkin as Hugh Parkfield

Episode: “Lisa’s Wedding”, 1995

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Mandy Patinkin (AKA Homeland’s Saul, or Gideon from Criminal Minds) adopted an English accent to play Lisa’s posh fiancé Hugh Parkfield in a flash-forward episode. You’d never guess it was him.

Glenn Close as Mona Simpson

Episode: First appearance in “Mother Simpson”, 1995

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Glenn Close has appeared four times as Homer’s hippie mother, making her debut in 1995. She’s introduced in the episode “Mother Simpson”, having left Springfield in a hurry after destroying Mr Burns’ biological warfare experiments.

Mona has also been voiced by Pamela Hayden (who also plays Milhouse), due to Glenn Close being unable to say ‘d’oh’ properly. Aww.

Albert Brooks as Hank Scorpio

Episode: “You Only Move Twice”/”500 Keys”

Albert Brooks has been in seven episodes and played five different characters, the most memorable of which is definitely supervillain Hank Scorpio. Not only one of the best celebrity cameos, but one of the best minor characters on the show, period.

Fun fact: Brooks also voiced Marlin in Finding Nemo. What a turnaround.

Johnny Cash as Space Coyote

Episode: “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)”, 1997

That there is Johnny Cash. BlogSpot BlogSpot

In this surreal episode, Homer eats several ‘Guatemalan insanity peppers’ and hallucinates a spirit guide who called the Space Coyote – who is voiced by the legendary Johnny Cash, for some reason. Weird and wonderful.

Martin Sheen as The Real Seymour Skinner

Episode: “The Principal and the Pauper”, 1997

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This may be one of the most unpopular Simpsons episodes to date, but you can’t say it’s not memorable. Martin Sheen (chosen because of his role in Apocalypse Now) plays the real Seymour Skinner, with the current Skinner revealed to be an imposter called Armin Tamzarian. Bonkers.

Benedict Cumberbatch as the Prime Minister/Severus Snape

Episode: “Love Is A Many-Splintered Thing”, 2013

A more recent episode, but don’t hold that against it – that’s Sherlock star Benedict Cumberbatch popping up for all of one minute in a spoof of British films, Love Indubitably, as both a Hugh Grant-esque politician and Severus Snape.

As Cumberbatch tells it, he ‘muscled in’ to the parts after having a meeting in the same studio where the show records the voice-overs. What a lovely little accident.

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