Top 10 Guest Stars on The Simpsons (Who Play Characters)

Top 10 Guest Stars on The Simpsons (Who Play Characters)

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Top 10 Guest Stars on The Simpsons (Who Play Themselves)

These characters wouldn’t have been the same without the dulcet tones of celebrity guest-stars. Welcome to WatchMojo.com and today we’re counting down our picks for the top 10 celebrity cameos on “The Simpsons” who play characters. Narrowing this list down wasn’t easy, so these picks focus on celebrities that have played one prominent character in The Simpsons’ world, and not just a yellow version of themselves.

Bringing his trademark wit from the UK to Springfield is this writer and stand-up comic, who also helped write the episode. And his dry British comedy doesn’t do anything to disturb the classic Simpsons feel. His role sees him trying to woo Marge during a wife-swap scenario – which is surprisingly unsettling. Nevertheless, with cringe-worthy guitar numbers and brilliant comedic timing, Gervais’ performance will always stick in our minds.

Essentially playing a female version of Bart, this Oscar-winning actress brings plenty of cheekiness, fast-lipped wisecracks and “ay caramba” moments. As Reverend and Helen Lovejoy’s daughter, Jessica is a master manipulator with a soft and stern voice, which she uses to get Bart to do what she wants, when she wants – making this Bonnie and Clyde duo very entertaining. Oh, did you know Streep also voices Ned Flanders singing? Creepy.

#8: Lisa Kudrow as Alex Whitney “Lard of the Dance” (S10E01)

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Lisa Simpson is limited in what she knows of cell phones, boys and fashion – so it takes just one little know-it-all to spark her curiosity. Kudrow uses her bubbly nature to give us a character we can all relate to. Shopping at the mall, using new ‘hip’ lingo and at times, acting incredibly dumb, she’s a great contrast to the saxophone-playing sweetheart we’ve all come to love.

#7: Steve Martin as Ray Patterson “'Trash of the Titans” (S09E22)

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As Springfield sanitation commissioner Ray Patterson, Steve Martin wears his frustration on his sleeve as he’s trying desperately to get the people of Springfield to realise that Homer Simpson is, well, an idiot. The two square off in a battle of wits, sorta, as they’re running for Patterson’s job. But, it seems Springfieldians like Homer’s flair more. Anyway, Homer may win, but Patterson gets a last word.

What’s cooler than cool? The Man in Black, of course. Johnny Cash lends his chilled-out voice to a prophetic Coyote, who is in fact Homer’s spirit guide on his chili-induced bad trip. When he starts speaking of a deeper wisdom, Homer is naturally a little confused. Listening to Cash’s performance, we can’t help but wonder whether it was actually scripted, or if it’s just him being all philosophical and awesome.

In an episode that tackles a few heavy themes like adultery and marital values in a way only the Simpsons can, Pfeiffer manages to be both the likable love interest, and essentially, the villain. Her uninterruptible eating patterns, love of beer and tendency to slack off at work should make her the perfect partner for Homer. But, after a heart-warming journey of morality, Homer realises that Marge is the only one for him.

Even with his short stature off-screen, DeVito never fails to give his characters a big presence and a whole lotta life. Homer’s brother Herb is no different. A rags-to-riches automotive magnate, Herb lets Homer in on his business, only to have him ruin it with a ridiculous car idea. DeVito’s frustrated mannerism and tendency to snap are relatable from an estranged family point of view and a business one.

If anyone has a voice fit for cartoons, it’s him. As Mr. Burns’ long-lost son, Dangerfield’s caricature-like tone is perfect for getting under the old man’s skin. Dangerfield even makes his classic one-liners fit into the Simpson’s paradigm, which keeps us laughing throughout. We can’t decide what’s more impressive: the fact that Mr. Burns is capable of loving someone, or the fact that Dangerfield’s character looks incredibly like him.

#2: Kelsey Grammer as Sideshow Bob Various Episodes

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As Bart’s long-time nemesis and one of the town’s most evil men, Sideshow Bob is a certifiable nut-ball – and one of Springfield’s best peripheral characters. Thanks to Grammer’s exceptionally villainous portrayal of this complex character, we can’t help but feel sorry for the guy – even though he tries to kill Bart and many others on multiple occasions. Even so, we could still watch this fluffy-haired clown step on rakes all day. Before we unveil our number one pick, here are a few honorable mentions: - Ray Romano as Ray Magini “Don’t Fear the Roofer” (S16E16) - Gillian Anderson & David Duchovny as Agents Scully & Mulder “The Springfield Files” (S08E10) - Glen Close as Mona Simpson “Mother Simpson” (S07E08) - Eric Idle as Declan Desmond “’Scuse Me While I Miss the Sky” (S14E16) - Albert Brooks as Hank Scorpio “You Only Move Twice” (S08E02)

#1: Michael Jackson as Leon Kompowsky “Stark Raving Dad” (S03E01)

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MJ’s personality is bigger than ever in his somewhat secretive cameo role on “The Simpsons.” While confined to a mental institution, Homer befriends Leon and learns the moonwalk. Though the episode can be considered a commentary on the King of Pop’s somewhat strange personality, it still offers great insight into his tender nature. If Jackson’s smooth conversational tone isn’t enough to win you over, maybe Lisa’s birthday song will. Do you agree with our list? What’s your favorite Simpsons character played by a guest star? For more top 10s published daily, be sure to subscribe to WatchMojo.com.