20. Martin Sheen

Character: The 'real' Principal Skinner
Episode: 'The Principal And The Pauper', Season 9 ('97-'98)
According to producer Josh Weinstein, Sheen was chosen for the role of rigid military man and Vietnam vet Seymour Skinner because of his work as a scuzzy renegade-hunter in Apocalypse Now.
The actor aced his part as the prodigal disciplinarian, but the episode itself fared less well – it’s often held up as the first sign that the show's golden age was coming to an end.
19. James Woods

Character: Himself, researching a role at the Kwik-e Mart
Episode: 'Homer And Apu', Season 5 ('93-'94)
Woods was on a shortlist of actors that producer David Mirkin was desperate to feature on the show. When first-choice Michael Caine turned down a chance to appear as an actor preparing for an upcoming role, the script was rewritten for JW.
On top of his excellent ad-lib skills, the crew remember Woods for his habit of artful hesitating (all part of his regular anxious-menace schtick) which made his animated character seem more realistic.
18. Kirk Douglas

Character: Chester J. Jampwick, dispossessed Itchy & Scratchy creator
Episode: 'The Day The Violence Died', Season 7 ('95-'96)
Douglas wasn’t the first choice for grizzled down-and-out – and Itchy & Scratchy creator – Chester J Lampwick. That was Prizzi's Honour star William Hickey, who the producers described as "famous for being a grouchy, mean old man".
But Douglas could hardly have been grouchier. He refused to wear the headphones during recording as they hurt his ears (meaning he couldn’t hear direction from outside the booth) and refused to do more than two takes per line.





Comments
Lindz28
Apr 8th 2009, 11:29
Can you do a South Park list as an companion to this one? I'm thinking Mel Gibson bouncing around smearing poo everywhere!!
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avoidz
Apr 9th 2009, 6:25
Notice how all the great guest star appearances are all in the early- mid-1990's Simpsons episodes?
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Ominater
Apr 10th 2009, 18:13
I reckon Tony Blair should have been on this, in the episode where the Simpsons go to London
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TazzaWazza
Apr 28th 2009, 1:48
@Ominater Tony Blair is not a movie-star, though he was one hell of an actor...oh, a bit controversial there.
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idbjoshm
Jun 19th 2009, 7:34
I'm not sure if I missed it or not, I re read the article. But it is a travesty that Glenn Close wasn't even mentioned as Homer's mother! It's along the same mention as liz taylor as Maggie's voice. Just like Maggie's first word as a milestone, Homer finding out that his mother is alive should at least be mentioned as the top 5.
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stevolbauer
Jul 2nd 2010, 15:18
U2 were by far the best geust stars, they send themselves up terrifically Bono: Hes talking about waste management, that effects the whole damn system The Edge: Here he goes again
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