This article comes from Den of Geek UK.
In compiling a list of these great one-episode wonders, the show’s longevity makes it harder than you’d think. Characters who are most memorable for their first episodes, like Mindy Simmons, Hollis Hurlbut, and Mr Bergstrom, have all recurred in more recent episodes in one form or another, and so we haven’t featured them in the following round-up.
Furthermore, we’re not counting celebrities playing themselves in guest spots or any of the various could-have-been and never-were characters from ‘Treehouse Of Horror’ specials.
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Other than that, we’ve come up with a wide array of characters, ranging from characters who are designed as punchlines to interlopers who shake up the status quo for exactly one episode.
Don’t forget, our ranking is not only utterly arbitrary, but also extremely final, thank you, come again. Only joking – feel free to chip in any we’ve missed in the comments!
31. Guy Incognito
30. L.T. Smash
After the turn of the century, episodes like “New Kids On The Blecch” are often only as good as their one-off characters. One of many unique characters voiced by the great Hank Azaria in this period of the show, the Party Posse manager removes a dot from his nameplate when he’s outed as US Navy recruiter Lieutenant Smash. “Yvan eht nioj” indeed…
29. Lucius Sweet
28. The Australian Prime Minister (“Andy!”)
The Simpsons’ trip down under in “Bart vs. Australia” does little to dispel the Australian stereotypes popularized by Crocodile Dundee. It even invents a few new ones, including the idea that the stars on the flag represent a hard, punitive kick up the arse that stands as the nation’s oldest tradition. That ritual is here upheld by PM Andy, a bloke who spends his days off floating on a lilo with a Foster’s, where his constituents can reach him.
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27. Leavelle
You don’t get a voice actor of Mark Hamill’s calibre to only play himself. That’s why he has a dual role in Season 10’s “Mayored To The Mob,” also serving as bodyguard academy instructor Leavelle. More or less unrecognizable as Hamill’s voice, he puts his trainees through their paces before congratulating them on their graduation with a rendition of Whitney Houston’s theme song from The Bodyguard.
26. Dexter Colt
25. Don Brodka
In a similar vein, Lawrence Tierney’s store detective is one of the most memorable parts of the festive episode “Marge Not Be Proud.” After catching Bart taking a five-finger discount on a new video game at the Try-N-Save, Brodka doesn’t have to go so above and beyond to keep him out, but he’s still unnecessarily hard-boiled for his position.
24. Mrs. Burns
23. The Southern Cracker Executive
“Kirk, crackers are a family food, happy families. Maybe single people eat crackers, we don’t know. Frankly, we don’t want to know.” Most of the recurring characters on The Simpsons have had at least one episode dedicated to them over the years, and “A Milhouse Divided” gives us a closer look at Kirk and LuAnn Van Houten. As their marriage goes down the toilet, so too does Kirk’s job, as his boss at Southern Cracker says goodbye and not good luck.
22. The Cayman Islands Banker
When Krusty’s off-shore tax evasion scheme is exposed in “Bart The Fink,” we get a perfect pocket cutaway to this loose-lipped fat cat who fans himself as he sells the celebrity clown up the river. What more is there to say? Oh crap – he’s another one-joke character. Oh crap – he’s another one who doesn’t have a name. Oh crap – we could have picked Handsome Pete, from the same episode! Ugh, it’s too hot today…
21. Godfrey Jones
read more: Exploring The Simpsons Early Shorts
20. Number One
19. The Tall Guy in a Small Car
Right at the end of the ’90s indie movie pastiche ’22 Short Films About Springfield’, this fellow shows up to give Nelson his comeuppance for years of haw-haws. When this lofty gentleman unfolds himself from his affordable but compact vehicle and marches the bully down Main Street with his pants around his ankles, the town cheers him on. As one of the taller writers here at DoG Towers, I stand for a lanky hero.
18. M. Lacoste
In “The Boy Who Knew Too Much,” Bart witnesses an altercation between the mayor’s nephew Freddy Quimby (who turns up in later episodes, before you ask) and French waiter Monsieur Lacoste. The episode hinges on the fact that he’s not the victim of a brutal beating but just an exceptionally clumsy individual, including “Clouseau-esque” cartoon slapstick galore.
17. Dean Bobby Peterson
16. Roy
15. Jessica Lovejoy
Meryl Streep’s guest spot in Season 6’s “Bart’s Girlfriend” kicked off a trend of famous actresses guesting as Bart’s love interests, continuing right up to Amy Poehler’s recurring role as his future wife Jenda. But with Streep evidently enjoying the contrast of the innocent reverend’s daughter turning out to be even more satanic than Bart, Jessica Lovejoy is one of the most memorable.
14. Ray Patterson
13. Mr. Black
Originally touted as a plot for a potential Simpsons movie, season four’s “Kamp Krusty” sees Bart, Lisa, and the kids of Springfield go on a long-anticipated trip to summer camp. But rather than the holiday of their dreams, they find that the Krusty Corporation-approved getaway is practically a gulag, ran by humorless suit Mr. Black. Voiced by Harry Shearer at his most deadpan, he epitomises both banality and cruelty even before he gives the iconic toast, “Gentlemen, to evil!”
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12, 11. Zutroy/Joey JoJo Shabadoo Jr
10. The Peanut Factory Manager
Somewhere in Springfield, there was a peanut factory manager who made all of his employees train for two hours every morning, just in case there was ever an elephant on the loose. And in “Bart Gets An Elephant,” his nightmare comes to pass. One of the show’s all-time most sublimely absurd one-joke characters.
9. Rex Banner
8. Shary Bobbins
Your mileage may vary on whether the Mary Poppins parody ‘Supercalifragilisticexpiali(Annoyed Grunt)’ was a triumph or a sign of things to come, but in the centre of it, Shary Bobbins makes a cracking off-Disney parody who’s hilariously fleshed out over the episode’s running time. Whether it’s her doomed engagement to Groundskeeper Willie or her unnoticed demise, more work is put into her than the central piss-take might suggest.
7. Karl
6. Leon Kompowski
As of 2019, “Stark Raving Dad” has been withdrawn from circulation in the light of further revelations about former guest star Michael Jackson in the documentary Leaving Neverland. Truthfully, this feels like a hasty decision, because it’s not an episode about Jackson, but an episode about Leon, a big, angry guy who thinks he’ll be less threatening if he pretends to be someone else, resulting in an episode that has only gained more meaning over time.
5. Chester J. Lampwick
Season 7’s “The Day The Violence Died” reveals that Itchy & Scratchy was plagiarized from animation genius-turned-bum Chester J. Lampwick (voiced by Kirk Douglas), who drafts Bart and Lisa to help him get his dues – namely a rocket car and a solid gold house. With his righteous indignation about his legacy and his half-assed approach to the gig economy (“Paint my chicken coop!” “Make me!”), Chester’s fleeting role in the history of the show-within-a-show is still unforgettable.
4. Mr. McGreg
3. Molloy
2. Lyle Lanley
Some characters are even more memorable as their big catchy musical number. Voiced by the late, great Phil Hartman and inspired by The Music Man, Lanley is a grinning, amoral huckster who, in his own words, sees a town with money as a mule with a spinning wheel (“Heheh, mule”) and more or less gets away with fleecing Springfield. Fortunately, he gets his head kicked in upon accidentally returning to North Haverbrook, another town he conned.
1. Hank Scorpio
At one point in development, Scorpio was intended to be the returning villain of The Simpsons Movie, but Brooks instead played another new antagonist, EPA head Russ Cargill. That’s for the best, because the motormouthed tech boss represents the peak of the show’s knack for memorable and frankly unrepeatable mayfly characters.
