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.
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.
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.[page-break]
Character: John, Homer’s gay buddy
Episode: 'Homer’s Phobia', Season 8 ('96-'97)
Waters agreed to appear as the Simpons’ stylish camp family friend because, as he told producers, “If it’s good enough for Liz Taylor, it’s good enough for me...”
The episode is a sensitive and sharp critique of knee-jerk intolerance, but John/Waters steals the show with a barrage of ultra-camp, catty zingers (“Helen Lovejoy – sure, she looks blonde, but I’ve heard cuffs and collar don’t match, if you get my drift.”)
Character: Mr. Bergstrom, Lisa’s inspirational substitute teacher
Episode: 'Lisa’s Substitute', Season 2 ('90-'91)
Hoffman was one of the show’s earliest big-name guests (“I'm Mr. Bergstrom. Feel free to make fun of my name if you want. Two suggestions are 'Mr. Nerd-strom' and 'Mr. Booger-strom') but, weirdly, he didn’t appear under his own name.
Instead, Hoffman used the pseudonym ‘Sam Etic’ - supposedly thought up by James L. Brooks as a reference to Hoffman and his character’s Jewishness (Semitic – geddit?).
Character: Mindy Simmons, Homer’s would-be soulmate
Episode: 'The Last Temptation Of Homer', Season 5 ('93-'94)
Despite being initially nervous, Pfeiffer was a big hit with the Simpsons’ crew when she came in to record her part as Homer’s donut-loving co-worker Mindy.
She wasn’t afraid to ditch her glamorous image to really nail the part – to get her dessert-induced drooling noise just right, Pfeiffer went Method - stuffing her mouth full of water and broccoli.[page-break]
Character: Hollis Hurlbut, head of the Springfield Historical Society
Episode: 'Lisa The Iconoclast', Season 7 ('95-'96)
According to producer Bill Oakley, the part of fatherly but lie-peddling historian Hurlbut was written with Sutherland in mind.
Sutherland wanted to start voicing the script in the middle - as he would in a film - in order to get to know the character better, but this wasn’t possible and he had to ditch the thesping and just get on with it.
Weird fact: Sutherland had earlier played a character called Homer Simpson in The Day Of The Locust (1975).
Character: Himself, opening Sprinfield’s new monorail system
Episode: 'Marge Vs. The Monorail', Season 4 ('92-'93)
Nimoy was so good as a sci-fi nerd-baiting version of himself unveiling the town’s new monorail (“I’d say this vessel could do at least Warp 5!”) that he came back to do it all again for the show's X-Files tie-in.
George Takei was offered the part first, but turned it down on grounds that he thought it might conflict with his position on the Southern California Rapid Transit District board of directors. Diva!
Character: Himself, visiting the comic-book store
Episode: 'I Am Furious, Yellow', Season 13 (2001-2002)
The creator of Spider-Man and the Hulk (whose green fury is a big influence on the episode) appears as a deranged, childish and brilliant version of himself in Springfield’s comic-book store...
Stan Lee: “Hold it son. Wouldn't you rather have an exciting action figure?”
Database: “Ahh, but only Batman fits in my Batmobile.”
Stan Lee: “Are you nuts? The Thing fits in there perfectly. Look, he's fitting right now.”
Database: “AHH! You broke my Batmobile!”
Stan Lee: “Broke? Or made it better?"[page-break]
Character: Himself, as a charitable pop-star digging Bart out of a well
Episode: 'Radio Bart', Season 3 (1991-'92)
It’s weird to think that Bruce Springsteen was the producer’s first choice for the part of a puffed-up charidee-doing rocker, since Sting, with his Live Aid performances and general air of serene self-righteousness, is so utterly perfect.
“There's a hole in my heart, as deep as a well, For that poor little boy who's stuck halfway to Hell...” he sings in the cheese-riffic tribute song. Props to the Tantric warrior for not being afraid to mug himself.
Character: Herb Powell, Homer’s long lost brother
Episode: 'Oh Brother, Where Art Thou?', Season 2 (1990-'91) - and 'Brother Can You Spare Two Dimes?', Season 3 (1991-'92)
DeVito brought his wise guy warmth and down-and-out charm to the role of Herb, the (much smarter) brother Homer never knew he had.
Such was DeVito’s pull on audiences that after the sad ending of the first episode (Homer bankrupts Herb’s successful car manufacturing business) a happier follow-up was made in which Herb gets rich again by inventing a machine that translates baby noises. Like this one…
Character: 'Number One', leader of the Freemason-like Stone Cutters Society
Episode: 'Homer The Great', Season 6 (1994-'95)
High praise all round for the sonorous Mr Stewart. Producer David Mirkin describes the actor’s secret-sect leader as “one of the best guest performances", while the actor himself gushes, “I think my appearance in The Simpsons, and an appearance that I did on Sesame Street, in praise of the letter 'B', were perhaps the two most distinguished bits of work that I've done in the US.”
Presumably he was speaking before X-Men , but even then – the letter 'B' is strong .[page-break]
Episode: 'Radioactive Man', Series 7 (1995-'96)
Rooney is desperately funny and self-effacing as a parody of his fallen child-star self (the cartoon image of him squeezed into Milhouse’s spandex Fallout Boy outfit is equally disturbing and priceless).
He was a joy to work with, too. Nancy 'Bart' Cartwright remembers him being happy to do all his voice work alongside the other actors (unusual, apparently) and being “full of pep”.
Episode: 'Beyond Blunderdome', Season 11 (1999-2000)
Another ace self-effacing appearance from a Hollywood high-flyer, this time with Mel Gibson taking notes on his latest blockbuster from a jealous, idiot-brained Homer.
The result: a remake of Mr Smith Goes To Washington in which every member of Congress is graphically slaughtered, with enough Tinseltown in-jokes to kill a small horse (“I second that motion… with a vengeance ”).
Episode: 'Mr. Plow', Season 4 (1992-'93)
Episode writer Jon Vitti weaved West into the story just so he could finally meet the camp Batman legend.
West sends himself up brilliantly (“I didn't need a moulded plastic suit to improve my physique – pure West”). Matt Groening has since said that the TV star was one of the most popular guest performers among The Simpsons’ crew.[page-break]
Character: Jessica Lovejoy, Bart’s major crush and misbehaving equal
Episode: 'Bart’s Girlfriend', Season 6 (1994-'95)
Streep is the perfect mix of beguiling and devilish as Reverend Lovejoy’s rebellious daughter (“I told the Reverend I was going to my room to say my prayers…”).
Bart falls for her hard and fast, describing her to Lisa as like a Milk Dud – “Sweet on the outside, poison on the inside” – while producer David Mirkin praised Streep for her ability to be “easily evil” in her recording sessions.
Character: Mulder & Scully
Episode: 'The Springfield Files', Season 8 (1996-'97)
The celebrated X-Files crossover featuring Leonard Nimoy, the FBI and a luminous peace-preaching alien was made possible by the Fox factor.
While X-Files creator Chris Carter said it was “an honour” to be satirised by the Simpsons, Duchovny went even further and suggested they do a return cameo, with Simpsons characters appearing, Roger Rabbit-style, alongside Mulder and Scully. U... huh.[page-break]
Episode: 'Mayored To The Mob', Season 10 (1998-'99)
What’s not funny about Mark Hamill playing a bottomed-out version of himself plugging cheap ads at conventions (“You stupid nerds! He's trying to save you money on long distance!”) and singing ‘Luke Be A Jedi Tonight’ in a twisted version of Guys And Dolls?
Hamill actually played two roles in the show – as well as himself, he also voiced bodyguard trainer Leavelle. A little chippily, he said he preferred playing Leavelle...
Episode: 'When You Dish Upon A Star', Season 10 (1998-'99)
Bruce Springsteen was again first choice and again turned down the opportunity to play himself, this time as a star who moves to Springfield and is plagued by unwanted public attention. Demi Moore and Bruce Willis were also asked before Baldwin and Basinger signed up...
Now, it’s hard to imagine anyone else polishing their Oscars and suffering a Homer life invasion...
Baldwin: “Does anyone know where this came from?”
Homer: “Oh, there’s that script I wrote. Where did you find it?”
Baldwin: “On my pillow.”[page-break]
Character: Maggie Simpson
'Lisa’s First Word', Season 4 (1992-'93)
Liz hits the top spot for two reasons...
Firstly, because Maggie’s first word was amajor milestone for the series, and by taking the part, Taylor pretty much became an instant honorary member of the Simpsons cast.
Second, because she’s a huge star - like the kind they don’t make any more. Even though she only had a single word to say (“Daddy!”) she had to record it a reported 24 times because it was considered just too sexy.
And then when she did nail it, Liz apparently walked out of the recording studio in exasperation, swearing. That’s proper acting.
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