The Simpsons’ Greatest One-Off Characters

Since 1989, The Simpsons has built a massive roster of recurring characters, but what about the one-time greats of Springfield?

The Simpsons Guest Characters

This article comes from Den of Geek UK.

Since the first episode of The Simpsons aired in 1989, the show’s central cast of characters has expanded from Homer, Marge, Bart, Lisa, and Maggie to a roster of hundreds of instantly recognizable recurring characters. But as part of its singularly frenetic sitcom style, there are plenty of characters that never play a part in more than one episode.

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.

Even Frank Grimes, seemingly the ultimate one-off character in ‘Homer’s Enemy’, has been revisited, first through his (somehow) grown-up son and later in more ghostly and Halloween-y forms. But there’s a whole thing to be written about how the show has cannibalised itself in later seasons, and we aim to celebrate the ones who are still unique.

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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

Guy Incognito

There are a fair few sight gags on this list, so let’s start with a good one. After Homer is barred from Moe’s for an ill-advised prank, “Guy Incognito” tips up looking like Homer in disguise, asking for a drink. One beatdown from the patrons later, he’s tossed into the street, only for the actual Homer to stumble upon him. A near-perfect comic skit.

30. L.T. Smash

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…

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29. Lucius Sweet

Lucius Sweet

As rich and famous as Don King (“and he looks just like him”), Moe’s former boxing manager also has all the charm and hidden malice of other Don King surrogates in TV and movies. Introduced alongside the more commonly seen Mike Tyson knock-off Drederick Tatum, he arranges a heavyweight championship bout in the hope that Homer can “retain verticality” for more rounds than the champ’s usual opponents.

28. The Australian Prime Minister (“Andy!”)

The Australian Prime Minister

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.

27. Leavelle

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

Dexter Colt

Another Azaria character, this private detective is hired by Homer to track Lisa’s interests and movements in “The Dad Who Knew Too Little.” The genre-savvy gumshoe is suitably out of place in a story that stems from Homer overreacting to a simple problem, whether he’s grilling Ralph Wiggum for information or declaring “From the moment you walked into my office, I had a feeling I’d kill you in a hall of mirrors” during the climax.

25. Don Brodka

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.

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24. Mrs. Burns

Mrs. Burns

Although C. Montgomery Burns’ age has fluctuated throughout the show, he remains Springfield’s oldest and meanest man, so it’s just one step beyond for “Homer The Smithers” to reveal that his even older mother is still alive, though so infirm she can only dial a phone and yell. Then again, mother and son aren’t on speaking terms – she thinks of him as an “improvident lackwit” and he still hasn’t forgiven her for her affair with President Taft.

23. The Southern Cracker Executive

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

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

Godfrey Jones

After Homer is accused of sexual harassment by the Simpsons’ babysitter, he seeks an outlet for his (admittedly implausible) side of the story and finds investigative news program Rock Bottom. Godfrey Jones is the show’s disingenuous host, who’s directly involved in editing Homer’s interview to make him look more like a fiendish predator. He’s still less sensational than some of the news personalities on US TV today, mind.

read more: Exploring The Simpsons Early Shorts

20. Number One

Number One

Their Number One, our number 20 – the Stonecutters’ leader makes a lasting impression with just one appearance in “Homer the Great.” All else aside, who else but guest star Patrick Stewart could bring the required gravitas to lines like “The Paddling of the Swollen Ass” or “Remove the Stone of Shame and attach the Stone of Triumph”?

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19. The Tall Guy in a Small Car

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

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

Dean Bobby Peterson

The ideal, nonplussed foil for Homer’s Animal House-shenanigans, the Dean of Springfield University isn’t the stuffed shirt that usually fills this role. Indeed, he seems like a nice guy, who’s genuinely regretful about expelling students for kidnapping Springfield A&M mascot Sir Oinks-A-Lot (goddamn you, Nixon) and is even relatively cool with being run over by Homer at the end.

16. Roy

Roy

Did you know that The Itchy & Scratchy & Poochie Show was the Simpsons writers’ rebuttal to a Fox executive asking them to have a new character move in with the family? As well as the utter failure of the Homer-voiced, none-more-90s doggo, the episode gives us Roy, a teen who very briefly lives at 742 Evergreen Terrace before moving out to live with “two sexy ladies”. Almost 20 years on, the Simpsons have yet to take in any other hip and happening new characters.

15. Jessica Lovejoy

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

Ray Patterson

Steve Martin guest-starred in the 200th episode as Springfield’s sanitation commissioner Ray Patterson, who is unseated when Homer’s attempts to get out of putting the bins out lead to a populist shake-up of the town’s political status quo. Unusually, Martin plays it more or less straight, and the character is all the more memorable for his final dripping contempt for Springfield. (“You’re screwed. Thank you. Bye.”) Maybe he’s not the politician we need, but he’s probably the one we deserve at this point.

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13. Mr. Black

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!”

12, 11. Zutroy/Joey JoJo Shabadoo Jr

Zutroy/Joey JoJo Shabadoo Jr

As mentioned, Mindy Simmons won’t go on this list because she’s popped up in later appearances. But beyond the sweet and touching A-plot that reaffirms Homer’s love for Marge, “The Last Temptation of Homer” is also an all-timer for one-off characters, ranging from Zutroy, the dangerously unqualified illegal alien who Mr Burns insists is “as American as apple pie”, to Joey JoJo Shabadoo Jr, who flees Moe’s in tears after the bartender says he has a stupid name.

10. The Peanut Factory Manager

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

Rex Banner

In keeping with the prohibition plot of “Homer vs. The Eighteenth Amendment,” Banner is an old-timey enforcement agent who arrives in Springfield to get the hooch off the streets. He departs not long afterwards via catapult (obv), but in the meantime, Dave Thomas plays his perfectly ridiculous character to the hilt, right down to night-time shouting matches with the mysterious Beer Baron.

8. Shary Bobbins

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

Karl

Not to be confused with Carl Carlson, Karl becomes Homer’s secretary at the power plant after he grows his hair back and wins an executive position in Season 2’s “Simpson & Delilah.” Voiced by Harvey Fierstein, he’s the show’s first openly gay character, but his commitment to his boss is played as a more platonic version of Smithers’ devotion to Mr Burns, right down to taking the fall for Homer’s misdeeds towards the end of the episode.

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Fierstein later declined to return as Karl for Season 14’s “Three Gays Of The Condo,” which saw Homer move in with gay roommates after being kicked out by Marge. The actor stated that it didn’t have the kind of clever angle that attracted him to the first episode, which is pretty par for the course when comparing earlier Simpsons scripts to later ones.

6. Leon Kompowski

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

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

Mr. McGreg

Turning up at the finale of “Homer’s Triple Bypass,” Mr. McGreg is a one-joke character, but we rank him so highly because the joke is an absolute doozy. Just as Dr Nick Rivera completes the titular operation, his “old friend”, a former patient “with a leg for an arm, and an arm for a leg” turns up as the punchline to his ongoing surgical incompetence. An unimprovable sight gag that the writers throw as far as their leg-arm will carry it.

3. Molloy

Molloy

Appearing in “Homer the Vigilante,” this suave resident of the Springfield Retirement Castle has it all – a silver-fox deftness, the dulcet tones of guest star Sam Neill, and (most tellingly) the world’s largest cubic zirconia on his coffee table. From his one-sided battle of wits with Homer to his final deception of the greedy townspeople, the senior cat burglar is one of the show’s funniest-ever antagonists.

2. Lyle Lanley

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.

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1. Hank Scorpio

Hank Scorpio

We’ve written before about the majesty of Albert Brooks’ guest appearances on the show, but it’s his turn as avuncular supervillain Hank Scorpio that elevates “You Only Move Twice” into a classic. After Homer is headhunted by Scorpio’s Globex Corporation, the family moves to idyllic Cypress Creek and never has a clue about his (successful) plot to take over the East Coast.

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.

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