Pinning down when the so-called “golden age” of The Simpsons took place is a matter of personal taste - some choose to cast a larger net but most will generally place it within those first nine or 10 seasons. One of the reasons for the show's unmatched quality in that period was the frequency of the outstanding guest characters who weren't simply celebrities playing themselves. To be sure, there were still plenty of celebrity cameos even when the show was at its peak, but the very best performances came from actors playing unique characters.
This collection takes a look back at the greatest guest performances in that era. The rules, which will be enforced arbitrarily, exclude celebrity cameos and recurring characters. As much as we love the likes of Sideshow Bob, Lionel Hutz, and Troy McClure, they won't be found here, for this list is for the characters who shone for one episode between Seasons 1-9. From the brilliant, benevolent billionaire seeking world domination to Homer's spiritual guide, this list asks the burning question: Who really was the best one-episode golden-age character?
- Photo: The Simpsons / Fox1787 VOTES
Episode: S2 E8 “You Only Move Twice”
Voice Actor: Albert Brooks
Scorpio: “You ever see a guy say goodbye to a shoe?”
Homer: “Yes, once.”
Scorpio: "By the way Homer, what's your least favorite country? Italy or France?
Scorpio: "Ha-ha. Nobody ever says Italy."
“But Homer, on your way out, if you want to kill somebody, it would help me a lot.”
He might be an evil tyrant hell-bent on world domination, but he's also a bold pioneer (he was the first wealthy man to wear jeans and a sport coat after all), skilled at sleight of hand tricks, and a great boss. The juxtaposition of a classic Bond villain being a supportive employer makes every Scorpio scene a delight. One moment he’s having a heartfelt talk with Homer, the next he’s chasing soldiers with a flamethrower while laughing maniacally.
- 2617 VOTES
Episode: S8 E23
Voice Actor: Hank Azaria
Grimes: “But this was a contest for children!”
Lenny: “Yeah - and Homer beat their brains out!”
"What's this? Extremely high voltage? Well, I don't need safety gloves because I'm Homer S-" (Grimes's last words)
Ol' Grimey was a decent, hardworking man driven to madness trying to make sense of Homer's cushy lifestyle achieved on the back of such little effort. He saves Homer's life but only gets a reduction in salary for his efforts. When his scheme to expose Homer's incompetence backfires completely, he snaps. His funeral is one of the most darkly comic scenes in the show's entire run.
- Photo: Fox3615 VOTES
Episode: S3 E1 “Stark Raving Dad”
Voice Actor: Michael Jackson (credited as John Jay Smith), Kipp Lennon (singing), Hank Azaria (real voice)
Kompowksy: “I'm Michael Jackson, from the Jacksons.”
Homer: “I'm Homer Simpson, from the Simpsons.”
Kompowsky (on the phone to Bart): “I'm Michael Jackson.”
Bart: “The Michael Jackson? No way.”
Kompowsky: “I'm with your father in a mental institution.”
Bart: “Uh-huh. And is Elvis with you?”
Kompowsky: “He could be. It's a big hospital.”
A very angry bricklayer from New Jersey became less angry when he started talking like Michael Jackson. Kompowksy's hulking frame and gentle voice made for a classic visual gag and the episode had a sweet ending with Bart and Kompowksy performing a duet for Lisa's birthday.
The episode has since ignited a storm of controversy because of Jackson's involvement. The late singer wasn't actually credited for the role and didn't do the singing, either - Kipp Lennon impersonated Jackson for the singing parts. You'll be hard-pressed to watch the episode today, as it has been removed from streaming services and box sets.
- 4522 VOTES
Episodes: S2 E15 “Oh Brother Where Art Thou?” & S3 E24 “Brother Can You Spare Two Dimes?”
Voice Actor: Danny DeVito
"People don't want cars named after hungry old Greek broads!"
Bart: "Unky Herb, what advice would you give to a boy… who will most likely become a bum like yourself?"
Herb: “Discarded pizza boxes are an inexpensive source of cheese.”
Summary: Okay, yes, he's a two-time character - but do you really care? Danny DeVito's turn as Homer's long-lost half-brother made for a great pair of episodes in Seasons 2 and 3. An unbridled success until he learns he's a Simpson, Powell was the head of a successful car company until he hired Homer to design a car for the average man. Despite a feel that is “powerful like a gorilla yet soft and yielding like a Nerf ball,” the Homer causes the downfall of his company.
In the Season 3 episode, he knocks Homer down with a single punch - no mean feat - and eventually regains his fortune thanks to a loan from Homer.
- 5480 VOTES
Episode: S4 E12
Voice Actor: Phil Hartman
“I've sold monorails to Brockway, Ogdenville, and North Haverbrook... and by gum, it put them on the map!”
“You there, eating the paste.”
A conman with an answer for everything, Lanley pitches up to convince Springfield to spend a windfall on a wholly unnecessary monorail. Even Lisa's taken in by Lanley when he dodges her question by appealing to her intellectual vanity. He gets his comeuppance at a layover in North Haverbrook. Since he's never heard from again, he was quite probably beaten to death.
- Photo: Fox6440 VOTES
Episode: S8 E4 “Burns Baby Burns”
Voice Actor: Rodney Dangerfield
Socialite: "You must meet our daughter the debutante, she came out last spring."
Larry Burns: "Whoa put her back in, she's not done yet."
“Hey, Skipper, good to meet you. Where'd you start out, on the Merrimack? Hey, I should talk. I hope I look that good when I'm 200.”
Mr. Burns's oafish illegitimate son is played by comic legend Rodney Dangerfield, and boy did the writers make the most of it. Larry Burns specializes in pointing out everyone's foibles and has a line for every occasion, even when nobody else is present.