The 100 Greatest Simpsons Guest Stars

Comedy Lists
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79. Sab Shimono as Mr. Sparkle
Episode: “In Marge We Trust”
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The main plot of this episode is an entertaining and heartfelt exploration of faith featuring Marge and Reverend Lovejoy, but everyone just remembers it as the Mr. Sparkle episode. Likewise, Shimono is an accomplished film voice actor, but his turn as the coincidentally Homer-shaped Japanese fishbulb mascot outshines everything else on his IMDb page.

Memorable Quote:
[Translated from Japanese] “I’m disrespectful to dirt. Can you see that I am serious?”

78. Donald Sutherland as Hollis Hurlbut
Episode: “Lisa the Iconoclast”
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Kiefer has been on the show a few times, but his dad’s even-tempered performance as a hardcore historian has stood the test of time. Very few can pull off gravitas and steal a silver tongue from a corpse in the same episode.

Memorable Quote:
“That’s preposterous. Now get out! You’re banned from this Historical Society. You, and your children, and your children’s children! ...for 3 months.”

77 – 76. Paul and Linda McCartney
Episode: “Lisa the Vegetarian”
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Though not particularly funny, the sheer star power of the McCartneys in cartoon form is a little staggering. Paul in particular added a lot to The Simpsons mythos when he stipulated that his appearance hinged on Lisa’s vegetarian transformation remain for the rest of the series.

Memorable Quote:
“Linda and I both feel strongly about animal rights. In fact, if you play ‘Maybe I’m Amazed’ backwards, you’ll hear a recipe for a really ripping lentil soup.”

75. R. Lee Ermey as Col. Hapablap
Episode: “Sideshow Bob’s Last Gleaming”
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Ermey has played the same hard-nosed drill sergeant since Full Metal Jacket, but that’s what works so well here. Taking that no-nonsense attitude and applying it to goofy phrasing is comedy gold, and Ermey pulls it off without a hitch.

Memorable Quote:
“Sweet Enola Gay, Son! I’m going to come in there and corpse you up—corpse you up and mail you to mama!”

74. Mark Hamill
Episode: “Mayored to the Mob”
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Though he’ll forever be known as Luke Skywalker, Hamill has done some impressive voice work since the original Star Wars movies. Besides playing himself in the episode, he also has a turn at a couple other side characters in the episode.

Memorable Quote:
“You know, I’m here today as Luke Skywalker, but I’m also here to talk about Sprint. As you can see here, you stand up to save up to seventeen cents a month over the more dependable providers.”

73. Lisa Kudrow as Alex
Episode: “Lard of the Dance”
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As the cool new preppy kid in school, Kudrow pulls less from Phoebe on Friends and more from her turn as half of Romy and Michelle’s High School Reunion. It was a perfectly cromulent creative choice.

Memorable Quote:
Alex: “Calm down, Lisa. DMY.“
Lisa: “What’s DMY?“
Alex: “Don’t mess yourself.“
Lisa: “Eww.“
Alex: “Yeah, that’s why we changed it to DMY.“

72. Bob Hope
Episode: “Lisa the Beauty Queen”
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This is one of those times in The Simpsons’ early years when you could tell the show really made it. Though he’s been all over the world doing hundreds, probably thousands of shows in his life, getting Bob Hope is still a coup; one of his few lines reflected the fact.

Memorable Quote:
“Hello, this is Bob ‘What the hell am I doing in Springfield?’ Hope.”

71. Steve Allen
Episode: “‘Round Springfield”
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Another comedy juggernaut, Steve Allen’s stint is also short in what’s otherwise a Bleeding Gums Murphy-centric episode. Decades later, he was still at the top of his game, elevating even the few lines he had.

Memorable Quote:
How to Make Love to Steve Allen, from the author of Happiness Is a Naked Steve Allen, Journey to the Center of Steve Allen, and The Joy of Cooking Steve Allen.”

70. Betty White
Episode: “Missionary Impossible”
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On the list of things that make national treasure Betty White great, her one-off Simpsons bit is probably pretty far from the top. On the other hand, just saying Betty White out loud increases the chances of a Golden Girls episode appearing on TV, so we’ll go ahead and give her the spot.

Memorable Quote:
[during the PBS pledge drive] “And if you watch one minute without contributing, you’re a thief! A common thief!”

69 – 67. Daniel Clowes, Art Spiegelman and Alan Moore
Episode: “Husbands and Knives”
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These musclebound terrors are actually just Hulked-out versions of the most respected comic book writers and artists in the entire medium. Moore, the staunch anti-Hollywood creator of “Watchmen” and “V for Vendetta” was a particularly good get; of course it was Milhouse who begged him to sign “Watchmen Babies: V for Vacation.”

Memorable Quote:
Bart: “Alan Moore, you wrote my favorite issues of ‘Radioactive Man.’”
Alan Moore: “Oh really, so you liked that I made your favorite superhero a heroin-addicted jazz critic who’s not radioactive?”

66. Lawrence Tierney as Don Brodka
Episode: “Marge Be Not Proud”
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As fun as Tierney’s mall cop was the in the episode, the stories behind the scenes are even better. Apparently he outright refused to say lines that he didn’t like and added a weird Southern accent to everything else. If only Betty White was so crazy.

Memorable Quote:
“If I wanted smoke blown up my ass, I’d be at home with a pack of cigarettes and a short length of hose.”

65. Sam Neill as Molloy
Episode: “Homer the Vigilante”
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Most voice actors play younger, but few skew older like Neill did with elderly cat burglar Molloy. He’s almost unrecognizable—his silky, wizened accent sounds more like Pierce Brosnan’s dad than the guy from Jurassic Park.

Memorable Quote:
“I sincerely regret any inconvenience that I may have caused. And although I have stolen your material goods, let me assure you that your dear town has stolen my heart.”

64. Willie Nelson
Episode: “Behind the Laughter”
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Though he’d been on episodes previous, the making-of episode “Behind the Laughter” revealed that Nelson had strong ties to Springfield. Namely, he’d been bros with Dr. Julius Hibbert. Rumor has it that “Always on My Mind” is really about his Kegmeister.

Memorable Quote:
“I would do anything for Kegmeister Julius.”

63 – 62. David Duchovny and Gillian Anderson as Mulder and Scully
Episode: “The Springfield Files”
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Interviewed at Comic-Con, both actors admitted that they barely remember taping their sizable Simpsons roles at the height of The X-Files’ popularity. It shows in their nonplussed performances, but in a way it works; to paranormal investigators, even a case in a place as insane as Springfield is just another job.

Memorable Quote:
Mulder: “Are we alone in the universe? Impossible. When you consider the wonders that exist all around us… voodoo priests of Haiti, the Tibetan numerologists of Appalachia, the unsolved mysteries of Unsolved Mysteries… The truth is out there.”

61. Jeff Goldblum as MacArthur Parker
Episode: “A Fish Called Selma”
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Unlike fellow Jurassic Park star Sam Neill, Goldblum’s plays more of a side character as Troy McClure’s Hollywood agent. Still, Parker gets McClure to star in the Planet of the Apes musical, and no one can deny that the world is a better place for that.

Memorable Quote:
“Listen, you can’t buy that kind of P.R., but you can get it for nothing by having a baby, which, by the way, your insurance will cover, except for the deductible which I’ll reimburse you for if you get the part which you will if you have a baby.”

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