There so many characters-of-the-day in this show's long run that we have to group them by seasons.
- Voiced by: Marcia WallaceDebut: "Bart the Genius"
She is the fourth grade teacher at the "Enriched Learning Center for Gifted Children" that Bart briefly attended after cheating on an intelligence test.
- Foil: She is calm and nurturing to her students and encourages independence and creativity in a pedagogically progressive environment, which heavily contrasts Mrs. Krabappel.
- Voiced by: Susan BluDebut: "Moaning Lisa""
Howard is the cool kid at Noiseland Video Arcade who teaches Homer how to beat Bart at video-game boxing.
- Cool Shades: He wears sunglassess.
- Voiced by: Pamela HaydenDebut: "Moaning Lisa"
- Almighty Mom: Even Homer is scolded by her for playing video games with little children.
Jacques is a bowling instructor who pursued an affair with Marge Simpson.
- The Casanova: Jacques is somewhat of a Casanova and mainly seems to try to seduce his clients instead of actually teaching them anything.
- Everything's Sexier in French: Has a French accent and is a Casanova.
Shauna Tifton A.K.A. Princess Kashmir
- Voiced by: Maggie RoswellDebut: "Homer's Night Out"
Princess Kashmir (real name Shauna Tifton) is an exotic dancer.
- Belly Dancer: She's dressed as a belly dancer for a bachelor party and has often appeared in her belly dancer garb in other episodes.
- The Cameo: Sometimes. In "Bart After Dark", for example, she appears doing a Fan Dance.
- Hooker with a Heart of Gold: In the episode "Radio Bart", Princess Kashmir is one of the celebrities who volunteer to sing with Sting on the song "We're Sending Our Love Down the Well."
- Really Gets Around: She has been seen with many men, including Apu (before his marriage to Manjula) and his brother Sanjay, Dr. Nick, Otto, Sideshow Mel, Hans Moleman, and even the married Chief Wiggum.
- Recurring Extra: She gets multiple cameos in the show.
- What, Exactly, Is His Job?: According to her career rundown in "Homer's Night Out", Shauna Tifton is a stripper for nearly every gentlemen's club in Springfield under many names, such as "April Flowers". She also works as a belly dancer for bachelor parties and can be seen dancing at nightclubs. She is also somewhat of a celebrity in Springfield.
Ugolin and César
- Debut: "The Crepes of Wrath"
Ugolin and Ceaser are two French wine makers who force Bart to be their slave using the foreign exchange student program.
- Bad Boss: They treat Bart like a slave by forcing him to do most of the work while they sit around and yell at him.
- French Jerk: Two hostile French wine makers.
- Jerkass: They are very mean men and they give Bart very little food, force him to sleep on the ground, and make him taste the Anti-Freeze filled wine.
- Knight of Cerebus: They treat Bart like a slave and could have killed him by giving him antifreeze-laced wine.
- Revenge Myopia: They return in the comics in a Villain Team-Up with Sideshow Bob against Bart for getting them arrested in their animated appearance. Bart even makes a lengthy expositional lampshade about all the crap they did to him first, and they essentially retort he was an Ungrateful Bastard over it.
- Would Hurt a Child: They treat Bart like a horse and risk his well being by testing antifreeze laced wine on him during their duration in the foreign exchange program. In a follow up appearance in the comics, they return from prison to try and kill him.
- Debut: "The Crepes of Wrath"
Adil Hoxha was a foreign exchange student from Albania. He stayed with the Simpson family while Bart was in France.
- Affably Evil: He's very polite to everyone and seems to genuinely like his foster family, even though he's a spy stealing nuclear secrets for Albania.
- Karma Houdini: He gets off Scott free for his crimes of espionage because The CIA And Albanian Intelligence do prisoner exchanges
- The Mole: He was discovered to be a Communist spy.
- Named After Somebody Famous: Named after then-Prime Minister Adil Carcani and former dictator Enver Hoxha.
- Voiced by: Penny MarshallDebut: "Some Enchanted Evening"
Lucille Botzcowski was once the babysitter of Bart, Lisa, and Maggie.
- Babysitter from Hell: Her true identity is a criminal who tried to rob the place after posing as babysitter. Bart, Lisa and Maggie manage to defeat her and flee to a pay phone.
- Karma Houdini: Homer unwittingly lets her get away, thinking she'd been beleaguered by Bart and Lisa.
- Karma Houdini Warranty: In Season 8's "Hurricane Neddy", she's shown among the inmates at the Calmwood Mental Hospital, which would suggest that she'd been arrested at some point between the two episodes.
- Knight of Cerebus: When she appears, things drift a lot further into Black Comedy territory.
- Voiced by: Harvey FiersteinDebut: "Simpson and Delilah"
Karl is a former diehard assistant of Homer.
- Guttural Growler: Has an extremely deep voice.
- Heroic Sacrifice: When Homer is exposed for using the company's health plan to buy the Dimoxinil for his hair, Karl takes the fall to avoid Homer getting fired.
- Hypercompetent Sidekick: To Homer.
- Sharp-Dressed Man: Karl is always seen dressed very well in suits of assorted colors and the occasional turtleneck and scarf.
- Straight Gay: Although it is never directly said, it is been suggested that Karl is homosexual. There are many indications as he kisses Homer during his pep talk and explains, "My mother taught me never to kiss a fool" before slapping Homer's buttocks.
- Taking the Heat: He willingly took the fall when Homer was about to be fired for insurance fraud.
- Undying Loyalty: He goes to nearly any length to ensure that Homer's career is successful.
Serak the Preparer
Serak the Preparer is a Rigellian who is the cohort of Kang and Kodos.
- Broken Tears: After the Simpsons think Kang and Kodos were trying to kill and eat them.Serak: I slaved in the kitchen for days for you people!
Master Sushi Chef
- Voiced by: Sab Shimono
A Japanese chef who works at The Happy Sumo.
A dog trainer brought in by the family to make Santa's Little Helper behave after he destroys several objects, most notably Marge's heirloom quilt. Her methods are harsh, belittling and seemingly ineffective on Santa's Little Helper.
- Deadpan Snarker: Often when Bart hasn't persuaded Santa's Little Helper to succeed.
- Defrosting Ice Queen: For most of the episode she's in, she's rude and unhelpful. But when Bart gets SLH to pass, she warmly comments "good show".
- Fair-Weather Mentor: Of a sort. She is full of praise for those dogs and owners who do well, but will belittle and be mean to those that fail.
- The Mean Brit: She's pretty damn rude, let's just put it that way.
- No Celebrities Were Harmed: She's a parody of Margaret Thatcher in her mannerisms. She was actually based on British dog trainer and author Barbara Woodhouse.
Beatrice "Bea" Simmons
- Voiced by: Audrey MeadowsDebut: "Old Money"
Grandpa Simpson's short-lived girlfriend.
- Death by Despair: Jasper and the others try to reassure Grampa that her death was natural (she died when a ventricle in her heart burst and staff were unable to save her), but Grampa is convinced — and makes sure Homer knows it — that Bea died of "a broken heart" (because he wasn't there to celebrate her birthday).
- The Lost Lenore: To Grandpa Simpson.
- Nice Girl: Very much so. Her ghost tells Abe that he should forgive Homer.
- Not-So-Imaginary Friend: Homer thought she was imagined by Grandpa because of his loneliness in the retirement home.
- We Hardly Knew Ye: She dies not long after we first see her. It's quite sad.
- Debut: "Brush with Greatness"
An art teacher at Springfield Community College.
- Bunny-Ears Lawyer: An eccentric artist that nurtures Marge's talent.
- Cool Teacher: He's very supporting and encouraging. He warmly praises all his students' work, and even praises the college custodian's work painting banisters and posters. He's also disgusted when he hears how Marge's high school art teacher Mr. Schindler insulted her work, considering the man a fool. His "Lombardo Method" for learning painting technique also helps Marge when she's practicing painting a portrait of Homer.
A substitute teacher who briefly takes over Miss Hoover's class when she comes to believe she has Lyme Disease. Enthusiastic, kind, and devoted to his students, Lisa soon begins to develop a Precocious Crush on him. He encounters Lisa and Homer once outside of the classroom, and sensing that something is lacking in their relationship and that Lisa is looking for that from him, he tries to inspire Homer to be a better role model for Lisa.
- Actually Pretty Funny: He encourages students to make fun of his name and is amused by a picture of him captioned with "the singing dork".
- But Now I Must Go: Accepts a job at another town and leaves Springfield.
- The Cameo: A few episodes have made references to him or he's shown up just briefly, including once when he stops by the Simpson house and Lisa doesn't realize he's there.
- Cool Teacher: He is an intelligent, sophisticated, dedicated, loving, excellent teacher who really does care about the students. He becomes a giant inspiration for Lisa.
- Dynamic Entry: He shows up in cowboy attire and fires off fake gunshots into the air, scaring the wits out of Vietnam veteran Skinner. These days, doing something like that wouldn't be tolerated, even if the guns were fake.
- Friend to All Children: One of the reasons he's so beloved.
- Master of None: Tells Lisa that in reality he and other substitute teachers are this knowledge wise, they know just enough about a whole bunch of subjects to teach it for a day or two.
- Nice Guy: Easily one of the best people to ever have been in Springfield.
- Real Men Wear Pink: He openly cries at the end of Charlotte's Web.
- Debut: "The Way We Was"
Marge's second Love Interest whom she found disgusting for his No Sense of Personal Space advances on her. Ever since their break up, Artie managed to hit it big in life but still holds a fervent torch for Marge after all these years.
- Abhorrent Admirer: To Marge, who found him disgusting.
- Ascended Extra: He appears for the first time in "The Way We Was" as a minor character of the Homer and Marge flashback. Later, he becomes the main focus in "Half-Decent Proposal" and "The Ziff Who Came to Dinner".
- Bolivian Army Ending: His last appearance thus far is during the end of "The Ziff Who Came To Dinner", where, upon being incarcerated, he begins spraying the cigarettes of all the fellow inmates. As an angry mob grows around him, Marge sadly tells the family to take one last look at Artie.
- Corrupt Corporate Executive: Of a corporation that is based off of Enron.
- Foil: To Homer. Being a genius, he got rich, powerful and earned respect, but he lives alone and the collection of Marge-resembling art around his mansion shows that he never got over Marge rejecting him. Unlike Homer, Artie only likes Marge for her aesthetic appeal and doesn't respect her opinions.
- It's All About Me: He has a big narcissistic love of himself.
- Jerkass: A facetious, self absorbed, and greedy jerkass who was first depicted as a popular and charismatic high school upperclassman that turned into an animal of a horndog trying to get it on with Marge post prom.
- He offers Marge and Homer a million dollars to have Marge stay with him for the weekend, saying that he won't try anything funny, and then tries to anyway. Then it's implied that he's spying on her through a camera in the mouthpiece that helps with Homer's snoring.
- When he is in debt and trying to escape from it, he bets his company in a poker game and Homer wins it, which directly ends up passing the debt on him and sentences him to jail. Artie keeps quiet even when Marge protests, though he comes to his senses in the end.
- Lonely at the Top: Despite his riches, Artie's life is not complete. He lives alone and the collection of Marge-resembling art around his mansion shows that he never got over Marge rejecting him.
- Love Redeems: In "The Ziff Who Came to Dinner", after framing Homer, Artie finally turns himself in after spending a night with Selma.
- Nerds Are Sexy: He was considered the hottest guy in school and popular among the ladies despite having the look of a stereotypical nerd.
- No Sense of Personal Space: If he keeps touching Marge for too long, his sensual behavior turns nasty.
- Put on a Bus to Hell: And came back for minor cameos. Can't say that his stay in prison was essentially a good time, however.
- Riches to Rags: In "The Ziff Who Came to Dinner", he reveals that he ran his company, Ziffcorp, into the ground spending investors money on such extravagant items such as marble toothbrushes and solid gold underpants. He was left penniless when the "dot-com bubble" burst, and secretly moved in the Simpsons attic to avoid capture.
- Stalker with a Crush: He hasn't forgotten about Marge after 20 years. And he has a room covered in pictures of Marge. Creepy.
- Too Dumb to Live: When Artie goes to prison, one of his first acts is to begin extinguishing other prisoners' cigarettes with a squirt bottle (allegedly to save their lungs). He is last seen continuing to squirt other prisoners' cigarettes while an ever-growing angry mob advances on him. What happened to Artie after that isn't known, and Marge provides some harrowing foreshadowing (unless you read the comics).
- Voiced by: Michael Jackson (credited as John Jay Smith), Kip Lennon (singing), and Hank Azaria (normal voice).Debut: "Stark Raving Dad"
Leon is a mental patient who thinks that he is Michael Jackson, but later confirms that he now knows that he isn't Jackson.
- The Bus Came Back: Leon makes an appearance in Mr. Lisa's Opus, 26 years after his debut, once again singing a happy birthday song to Lisa.
- But Now I Must Go: He leaves town after revealing he's not really Michael Jackson.
- Face of a Thug: He's a big, intimidating-looking guy that first shows up in a mental institution. He's also one of the kindest souls to ever show up in Springfield.
- Nice Guy: He's a kind-hearted, gentle, friendly, nice, musical, and caring man. He explains in his backstory that he used to be cranky, but after he learned to talk in a nice way, he learned that he could make people happy, so he decided to be a nice person.
- Vocal Dissonance: A large man with the smooth voice of Michael Jackson. It turns out it's not his natural voice, but a very good impersonation.
- Debut: "Mr. Lisa Goes to Washington"
The U.S. Congressman representing Springfield. He greets the Simpsons when they tour the Capitol, but later Lisa overhears him accepting a bribe from a lobbyist to secure a permit to chop down Springfield Forest.
- Bitch in Sheep's Clothing: At first, he seems like a decent guy, as evidenced by Moe and Barney's opinion of him, and even Lisa's.
- Broken Pedestal: Lisa looked up to him, hoping that she could vote for him once she's old enough.
- Corrupt Politician: He takes a bribe to demolish the forest that inspired Lisa's essay, and is willing to allow oil drilling on Teddy Roosevelt's head. Though that second one was a sting operation to have him arrested.
- HeelFaith Turn: According to a newspaper, he becomes a born-again Christian after his conviction. (This is a fairly obvious Take That! at the many Real Life criminals who claim to find religion in an attempt to win sympathy, and perhaps a reduced sentence.)
- Laser-Guided Karma: Lisa writes a second essay exposing his corruption, which leads to him getting caught in an FBI sting operation, expelled from Congress, and sent to prison.
- Debut: "Homer Defined"
The owner of the Shelbyville Nuclear Power Plant.
- The Rival: To Mr. Burns
- Voiced by: Jo Ann HarisDebut: "Flaming Moe's"
Colette is a waitress who worked at Flaming Moe's.
- Expy: Of Diane Chambers from Cheers.
- Morality Pet: To Moe. She discovers that Moe stole the recipe from Homer, and convinces him to sell the "Flaming Moe" for $1,000,000 and give half of the money to Homer.
- Voiced by: Beverly D'Angelo (Doris Grau in "Marge vs. The Monorail")Debut: "Colonel Homer"
Lurleen Lumpkin is an attractive, aspiring country western singer. Homer used to be her manager once.
- Alliterative Name: Lurleen Lumpkin.
- Because You Were Nice to Me: Lurleen falls in love with Homer because he is the first man in her life who treats her with respect and genuinely cares for her.
- The Bus Came Back: Lurleen Lumpkin returns in "Papa Don't Leech" and stays with the Simpsons (despite the fact Marge still really hates her after "Colonel Homer") so she can revive her dead career and search for her long-lost father.
- Country Music: Lurleen Lumpkin is a country musician.
- Hopeless Suitor: She quickly starts falling for Homer and it comes out in her song lyrics, but Homer remains oblivious. Then she makes an open attempt to seduce him with a seductive song called "Bunk with Me Tonight". Homer realizes that managing Lurleen could hurt his marriage, so he abruptly quits as her manager in the middle of a TV appearance and goes home.
- Parental Abandonment: His father Royce abandoned her when she was four years old. Marge realizes that because this, Lurleen had given up faith in all men and decides to get the two Lumpkins back on a proper parent-child relationship.
- Serial Spouse: When Lurleen returns, we find that she has been married 5 or 6 times, all to men that look and act just like Homer. At the end of the episode, she falls for yet another man who resembles Homer.
- Unknown Rival: Marge hates Lurleen to near-Yandere levels and wants her out of the family's lives out of fear she'll take Homer away from them. Lurleen mostly ignores her. Subverted in "Papa Don't Leech" where she is aware, mostly because Marge is really clear about this point:"If you ever come near Homer again, I'll strangle you with your own hair extensions. That's right, I know."
- Voiced by: Kimmy RobertsonDebut: "Bart's Friend Falls in Love"
Samantha Stankey is a new student at Springfield Elementary School and love interest for Milhouse.
- Alliterative Name: Samantha Stanky.
- Love Interest: To Milhouse.
- Nice Girl: She forgives Bart for telling her father about the romance with Milhouse.
- Put on a Bus: Her father sends her to an all-girl convent school, where she is locked away from the outside world, and she hasn't been seen or referenced since.
- Reused Character Design: Even though Samantha was put in an all-girls school and never mentioned again after her final kiss with Milhouse, there have been a number of girls that closely resemble her who have made brief cameos throughout the series (one of which attends Springfield Elementary).
- Sickeningly Sweethearts: She and Milhouse spend a great deal of time together kissing, making Bart feel left out in the process.
- Debut: "Bart's Friend Falls in Love"
Samantha Stankey's strict and overprotective father.
- Debut: "Kamp Krusty"
The camp director of Kamp Krusty.
- Bad Boss: Mr. Black does very little work, instead relying on the services of the school bullies Jimbo Jones, Dolph and, Kearney, who run the "Kamp Krusty" with an iron fist, to "crush their spirits".
- Card-Carrying Villain: He gives a toast saying "Gentlemen, to evil!"
- Debut: "A Streetcar Named Marge"
The musical director of Oh! Streetcar!.
- Bad Boss: By his own admission, he's not easy to work for, often driving cast members (including children) to tears.
- Bunny-Ears Lawyer: He's obnoxious, hammy, and possibly crazy, but the play is a smash hit.
- Incoming Ham: His intro is bursting through the door shouting, "HELLO?!"
- Jerk with a Heart of Gold: With a slight more emphasis on the Jerkass. He belittles everyone about everything, is quite demanding and somewhat of a perfectionist elitist when it comes to his work, and he even fires one of his play's cast-members (Otto) on the night of the performance, but he is passionate about his work, can see talent when it truly presents itself, does his best to draw out the best of his actors, and even if a bit vain, adores the audience, feeling they help make the production as it is as well. It's just that he's not without his flaws, like most of The Simpsons cast.
- Large Ham: The commentary notes that his bombastic introductory speech is actually the "smallest" take Lovitz did.
- Prima Donna Director: He actually winds up on stage when he takes over Otto's role right before the performance, having realized Otto wasn't good enough.
- Small Name, Big Ego: He carries around a good review he got for directing a fourth-grade play.Llwellyn Sinclair: Did I expect too much from fourth graders? The review "play enjoyed by all"... speaks for itself!
- Voiced by: Sara GilbertDebut: "New Kid on the Block"
Ruth Powers's teenage daughter, who Bart develops a crush on. Sadly for him, she already has Jimbo as a boyfriend. However, when Bart makes a prank call and Jimbo runs away crying like a wimp, she dumps him, and decides she might go on a date with Bart when he's older after all.
- All Girls Want Bad Boys: To Jimbo Jones, until she breaks up with him thanks to Bart's crank call.
- Chuck Cunningham Syndrome: She hasn't been seen after her first appearance. She is mentioned in "Marge on the Lam", when Ruth says she has to get home before her daughter watches that "naked talk show" and brought up in a story from Bart in Another Simpsons Clip Show, but she hasn't been seen since. Although seen in The Simpsons Movie as major background characters with her mother, only Ruth is seen out in Springfield's adult events, implying that Laura is out on her own and is having her own adventures as a young adult.
- Cool Big Sis: More or less acts like this towards Bart and to a lesser extent towards Lisa.
- Cool People Rebel Against Authority: Gives off a big vibe of this to Bart blended in with his Precocious Crush.
- Dad the Veteran: The one who probably gave his trenchcoat to her. Laura was also said to have been strictly disciplined as a child, as he held the once held rank of Corporal and presumably moved on up as seen on the rank on her trenchcoat. note
- Disappeared Dad: Mr. Powers (or "Powers" if Ruth's maiden name is in effect), who is just missing as a divorcee husband. Ruth however has very unflattering things to say about him.
- Deadpan Snarker: A very dry sense of humour.
- Distracted by the Sexy: Jimbo Jones appeals to Laura as her kind of guy. By the time of their second date though, he's expecting to get into her pants like the lowlife sex fiend he is.
- Freudian Excuse: Lightly implied with her love of "bad boys" and "quasi thugs". Considering her dysfunctional family life, she might has some daddy issues that are vaguely hinted to in retrospect considering Ruth's actions and motives in Marge On The Lam.
- Girl Next Door: Though she fits the bill of being next door, everything about her is charmingly subverted 1990s style. A lot more in line with Bart's mischief making and rebellious personality, but with a teenage street smart tomboy surface and a feminine side to show deeper in. Also pretty cultured and loves to mess with people psychologically.
- Generation Xerox: Whether she likes it or not, of her mother, Ruth Powers. Some In-Universe Harsher in Hindsight Sins Of The Mother too: if it weren't for Bart, Laura would have likely suffered the same kind of embittering dysfunctional love life her mother had with her divorced deadbeat dad, with a robbed teenage youth and jaded view on men in all.
- Horrible Judge of Character: Granted, though her rebellious spirit gets her to bond with Bart, this also gets her to stray off to jerkasses like Jimbo Jones and his friends when she isn't careful enough.
- Love Makes You Stupid: Dates one of the most abhorrent and loathsome people in Springfield, though to her credit and ignorance, she never knew him in full as she just moved to Springfield. Bart helps her see what kind of a loser Jimbo and his ilk really are.
- Military Brat: As strongly given image with her olive green military trenchcoat and her love for Middle Eastern food. Given that her father was in the military, she's most likely been with him to Afghanistan during his tour of duty during the Gulf War.
- Not So Above It All: Despite being a freewilled, authority sticking, and mischief loving teen, she'll easily fall in teenage sensation fangirling obsession if the target of her affections is but a "bad boy quasi thug", no questions about their character asked and all the hormones included.
- Precocious Crush: To Bart. Almost counts as First Love, because she's his first official Love Interest in the series. She even admits she might date Bart if he was closer to her age.
- Rebellious Spirit: As stated in her character profile, she dislikes authority.
- Tomboy: Laura has a tomboyish personality, but it is also her Charm Point.
- Used to Be a Sweet Kid: Of a lighter variety. She still is, but all of that painfully strict childhood upbringing was implied to have slingshot her personality a near 180 degrees.
- Voiced by: Phil HartmanDebut: "Marge vs. the Monorail"I've sold monorails to Brockway, Ogdenville and North Haverbrook, and by gum it put them all on the map!
A smarmy salesman (really a Con Artist) who comes to town just after Mr. Burns has been fined for pollution and the money is going over to the town. He shows up at the town hall meeting where the people are talking about how to use the money and convinces the town to build a monorail. He then steals most of the money while building the rail as cheaply as possible and in a substandard manner which is likely to fail.
- Alliterative Name: Lyle Lanley.
- The Cameo: In episode "Sky Police".
- Captain Ersatz: In costume and motivation, he is very similar to Harold Hill in the musical The Music Man, not to mention the fact that he talks in song. However, he displays absolutely none of Harold Hill's redeeming qualities.
- Con Man: A con artist and shyster who sold faulty monorails to several towns.
- Dirty Coward: Flees as soon as his scheme is completed, though to be fair he'd be stupid to hang around.
- Faux Affably Evil: Kind, flattering, charismatic, and friendly to all he talks to, he's also planning to scam Springfield out of a good deal and get many people killed in order to swindle a profit.
- Idiot Ball: He leaves his childishly drawn plans lying around in his office, where anyone could read them, which he even acknowledges is a stupid move.
- Laser-Guided Karma: After fleeing Springfield, he lands in another town he's swindled as his flight has to make a brief stop. He's promptly rushed by an angry mob and beaten.
- Manipulative Bastard: He not only charmed the whole town, but even got Lisa on his side.
- Oh, Crap!: When he realizes where his plane has stopped. See Laser-Guided Karma.Lanley: North Haverbrook, where have I heard that before? ...Oh no. OH NO!
- Uncertain Doom: He's last seen being brutally attacked by an enraged mob, and since he makes no more appearances afterwards even as a cameo, it's probably safe to assume he was killed. Not that he didn't deserve it.
- Voiced by: Michael CarringtonDebut: "I Love Lisa"
Krusty the Klown's sidekick before Sideshow Bob, likely from the 1970s era
- Angry Black Man: Krusty describes him as this.
- Palette Swap: He bears a striking resemblance to Disco Stu, except that he's black, has black hair, black glasses, and different clothes.
- Scary Black Man: So scary Krusty doesn't dare abuse him with pies to the face and other such pranks like he does to Sideshows Bob and Mel.
- Voiced by: Albert BrookDebut: "Bart's Inner Child"
Brad Goodman is a self-help guru who appears in "Bart's Inner Child".
- Snake Oil Salesman: As per Lisa, he's just selling a bunch of easy answers.
- Voiced by: Michelle PfeifferDebut: "The Last Temptation of Homer"
An attractive new employee at the power plant, Homer quickly develops a strong attraction to her, which is compounded by the revelation of their many similarities and the two being sent on a business trip together.
- Ambiguous Situation: More episodes later, Homer mentions that Mindy became an alcoholic and lost her job at the plant after his time with her, but future episodes "Team Homer" and "The Twisted World of Marge Simpson" show Mindy as sober and working at the plant.
- Big Eater: She likes junk food just as much as Homer (but somehow remains thin).
- Birds of a Feather: With Homer.
- Distaff Counterpart: She's a female Homer, except attractive. She likes cheeseburgers, a quick nap before lunch, foot-long chili dogs, whipped cream straight from the can, raspberry swirl doughnuts with a double glaze, drinking Duff beer, watching TV, and roasted anything. Mindy also has a tendency to drool like Homer when thinking about food and even uses his "Mmm..." catchphrase.
- Drowning My Sorrows: A later episode says that she became an alcoholic some time after the episode and was fired from the Plant as a result.
- Graceful Loser: When Homer confesses his feelings for Mindy but also says that he does truly love Marge as well, Mindy urges him to think about what he really wants. When he decides to remain with Marge, Mindy is shown as being okay with this and she and Homer part as Just Friends.
- The Lad-ette: She has Homer's personality in the body of an attractive woman. And she rides a motorcycle to work.
- Not Good with Rejection: Averted in the episode itself, where she's fine with Homer's decision. A throwaway line in a later episode however indicates that she took it hard and wound up depressed as a result.
Molloy the Cat Burglar
- Voiced by: Sam NeillDebut: "Homer the Vigilante"
Molloy is a cat burglar who lived at Springfield Retirement Castle.
- Affably Evil: Incredibly charming, so much so that he almost convinces the town to let him go.
- Batman Gambit: He tricks the entire police force into leaving him unguarded so that he can escape undetected.
- Crazy-Prepared: Left a briefcase with a signed confession buried on the edge of town, which he uses as a distraction should he ever be imprisoned.
- Gentleman Thief: After being caught at the end of the episode, he graciously returns the items he has stolen.
- Karma Houdini: Escapes from jail after sending the entire town on a Snipe Hunt.
- Voiced by: Kathleen TurnerDebut: "Lisa vs. Malibu Stacy"
Stacey Lovell is the creator of the Malibu Stacy franchise.
- Les Collaborateurs: The other reason she got kicked out of her company, for funnelling profits to the Viet Cong.
- Serial Spouse: Has 5 ex-husbands, Ken, Johnny West, G.I. Joe, Doctor Colossus, and Steve Austin.
- Debut: "Bart Gets an Elephant"
A big elephant that was given to Bart by the KBBL radio channel. He soon proved too much for the Simpsons to handle due to his size, and the enormous quantity of food he needed, so Homer initially tries to sell him to a poacher and ivory dealer. However, he changes his mind when Stampy saves him from drowning in tar, and decides (though not without some insistence from his kids) to release him in a wildlife preserve.
- The Bus Came Back: He reappears in "Large Marge", involved in a plan by Bart to help Krusty the Clown restore his public image.
- Jerkass: When introduced to other elephants, his first reaction was to headbutt them until they pass out.
- Debut: "The Boy Who Knew Too Much"
The nephew of Springfield's mayor, Joe Quimby.
- Berserk Button: Failing to pronounce the word "chowder" as "chow-dah". He once threatened to kill a room full of people in open court, because his attorney did so.
- Hypocritical Humor: Tries to mock the waiter's accented pronunciation of chowder. Not only does he have an accent of his own, but he is in fact incapable of decoupling his own accent from his mockery.
- Voiced by: Winona Ryder ("Lisa's Rival"), Pamela Hayden (subsequent appearances)Debut: "Lisa's Rival"
A girl in Springfield Elementary, who acts as Lisa's de-facto rival. Everything Lisa does, Allison can do better, despite being a year younger than her.
- The Ace: To the point that Lisa feels threatened by her.
- Always Someone Better: Is smarter, younger, more productive and a better saxophone player than Lisa.
- Child Prodigy: She's younger than Lisa, but she's even more of a prodigy than she is.
- Hair Decorations: A red headband.
- Fangirl: By the time she's introduced, of the same Bleeding Gums Murphy. She's even got an autographed photo of him, implying she presumably one upped Lisa by actually going to a show of his before his spiral downwards, but...
- Informed Attribute: Her Always Someone Better and Child Prodigy status eventually become this later on as she becomes but another Living Prop. Though Lisa might be flanderized (for better and for worse) in later seasons, she has a lot more achievements under her belt that makes Allison look like a thing of the past. This includes a touching first time meeting with Bleeding Gums Murphy, which helps Lisa ease and soothe her sorrows with his blues jazz with a musical spiritual experience, and being there at his deathbed, including helping spread his music throughout Springfield in reverence to him when he passes on.
- Innocently Insensitive: She seems to be completely oblivious to just how inferior she makes Lisa feel until the end of the episode.
- Living Prop: Allison can be later seen as a background character in many episodes revolving around the Springfield children. Presumably, it's down to not wanting to get Winona Ryder for one-off lines.
- Nice Girl: She's not actively malevolent in any way, just a rival.
- The Rival: Portrayed as such for Lisa.
- Debut: "Sideshow Bob Roberts"
Birchibald "Birch" T. Barlow is a right-wing conservative talk show host on the radio station KBBL. He also has a show on Fox News.
- Expy/No Celebrities Were Harmed: Of Rush Limbaugh. He even has a gold microphone.
- Fat Bastard: He's very abrasive to anyone who doesn't fit with his political beliefs.
- Meaningful Name: "Birch" is likely meant to be a reference to the infamous John Birch Society, a radical conservative/conspiracy theory group formed during the 1950s.
- The Nicknamer: Makes pejorative nicknames for anything remotely liberal, using alliterations and portmanteaus.
- Voiced by: Meryl StreepDebut: "Bart's Girlfriend"
Reverend and Helen Lovejoy's daughter, who feigns being as sweet and pleasant a girl as one would expect of a Reverend's daughter, but who is actually such a bad girl she unnerves Bart.
- All Girls Want Bad Boys: She's attracted to Bart because of his mischievous behavior. Subverted when it's revealed that she's even worse than Bart.
- Attention Whore: One of her last lines is demanding her father pay attention to her.
- The Bad Guy Wins: Subverted. She seemingly manages to seduce Bart into doing her punishment work at the end of her episode — when she leaves, he snickers about how bad a job he is going to do on the steps to get back at her.
- Bitch in Sheep's Clothing: Everyone believes that she's a sweet, innocent minister's daughter, but (much to Bart's dismay) she's actually a manipulative little bitch.
- Blue Boy Pink Girl: The pink girl to Bart's blue boy.
- Child Prodigy: She has an amazing I.Q. and reads at a higher grade level than normal. Subverted in that Bart only thinks she is; her I.Q. is 108 and she reads at a fifth grade level, both putting her only actually slightly above average, but enough to amaze Bart.
- The Cobbler's Children Have No Shoes: Of Reverend Lovejoy, of all people. When she is introduced, she is but a quiet but sweet little girl who had just come back from an all girls boarding school. As soon as the episode caps off, the real reason why she came back was because her want for attention eventually turned into a nasty want to become a child menace, including pranking to the point of causing on school rioting and property destruction. It appears that Lovejoy's ineptitude by laziness and apathy isn't just exclusive with Flanders, as he can't even morally console and instill his own daughter properly.
- Daddy's Girl: Which is the main reason she desires his attention so badly.
- Distaff Counterpart: To Bart.
- Eviler Than Thou: Her Jerkassness even scares Bart later on.
- Fille Fatale: Amongst boys smitten by her, she falls right into the role of femme fatale, and isn't afraid to use it.
- Freudian Excuse: Apparently the reason she acts like a total bad girl is because she craves attention, due to her father not giving her any.
- Jerkass: She makes Bart look like a saint in comparison.
- Jerk with a Heart of Jerk: Every time Bart seems to think he's talked Jessica into changing her ways, she screws him over.
- Kick the Dog: Talks Bart into going up to the top of an impossibly steep hill, then shoves him down it.
- Kids Are Cruel: A very naughty girl who's around Bart's age.
- Light Is Not Good: She wears a pink and white dress, and is definitely not good.
- Living Prop: After her debut episode, Jessica has since made cameos throughout the series. She also appears in the new opening sequence, playing the flute in the school's music class.
- Manipulative Bitch: She uses her beauty to manipulate boys and uses timidity to manipulate adults and girls.
- Pink Means Feminine: She usually wears pink and purple outfits.
- Preacher's Kid: She falls into the category of the rebellious troublemaker who pretends to be sweet and nice so that everyone thinks she's innocent and can do no wrong.
- Troll: Among the things she talks Bart into doing is eating ice-cream in front of overweight people exercising.
- Voiced by: Pamela HaydenDebut: "Homer Badman"
Ashley Grant is a graduate student and feminist who works as a babysitter.
- Easily Forgiven: Homer seems to hold no grudges for all the crap he's been through and quickly accepts Ashley's (albeit sincere) apology.
- Straw Feminist: Averted. Ashley (who falsely accuses Homer of sexual harassment) does feel that men can easily be manipulated by women and she does think Homer grabbed her butt in the car, but when she sees video evidence of what really happened, she realizes that she jumped the gun and apologizes.
- Debut: "Homer Badman"
Godfrey Jones is the host of the tabloid news program Rock Bottom.
- Bitch in Sheep's Clothing: Offers to help Homer, then uses his own words against him. When called out on this, his apology is a rushed list that scrolls by too fast to be read.
- Easily Forgiven: Homer seems to forgive Rock Bottom, despite what they did to him (and, unlike Ashley, their apology wasn't that sincere).
- Voiced by: Anne BancroftDebut: "Fear of Flying"
Dr. Zweig is a psychologist who helps Marge overcome her fear of flying.
- Blatant Lies: Says she's not going to judge anyone, as she immediately pegs Homer as a serious problem for Marge's mental health.
- Ignored Expert: Tries to talk about Homer, who immediately drags Marge away.
- Debut: "Fear of Flying"
A man who, except for having a mustache, slightly lighter-colored muzzle and an unusual accent, looks and sounds exactly like Homer.
- Identical Stranger: He looks exactly like Homer only with a mustache and speaking in a quasi-English accent.
- Riddle for the Ages: How or why does he look just like Homer? Homer wonders until he sees a dog with a puffy tail.
- Voiced by: Patrick StewartDebut: "Homer the Great"
The head of the local Stonecutters chapter.
- Card-Carrying Villain: Played for laughs, he and the other Stonecutters proudly sing about evil deeds that are mostly Poke the Poodle acts, but when Homer takes over and tries to actually make them do good acts, they quickly rebel.
- The Comically Serious: He's voiced by Patrick Stewart, who provides his usual Shakespearian delivery to everything the man says, including the Stonecutter's induction ritual, which involves asses and paddles.
- Only Known by Their Nickname: His real name is unknown.
- Start My Own: When he and the other Stonecutters disagree about the direction Homer's leadership takes them in, they start a new secret society that explicitly forbids Homer from joining.
- Debut: Homie the Clown
Don Vittorio Di Maggio is a commanding mafia leader. The mobsters of the Springfield mafia show him respect.
- Affably Evil: He's willing to spare Krusty and Homer's lives if they cam perform his favourite trick, and later allows Krusty to simply repay his debt to the mafia, even giving him change.
- Disproportionate Retribution: Almost has Krusty (and Homer) killed over a measly $48.
- The Don: And more powerful than Fat Tony.
- Voiced by: Phil HartmanDebut: "Bart vs. Australia"
Evan Conover is the "Undersecretary for International Protocol: Brat and Punk Division" and a member of the US State Department.
- "Ass" in Ambassador: Tries to hand Bart over to the irate Australian government repeatedly.
- Voiced by: Nancy CartwrightDebut: "Bart vs. Australia"
An Australian boy who was tricked into accepting a six-hour, $900 collect call from Bart.
- Expy: An Australia counterpart to the Flanders boys.
- Debut: "Bart vs. Australia"
- Beware the Silly Ones: Bart thought taunting Bruno over the phone would be enough to put his prank-calling behind him. He was wrong.
Gus the MP
- Debut: "Bart vs. Australia"
The Member of Parliament for Bruno Dundridge's district.
Prime Minister Andy
- Debut: "Bart vs. Australia"
Andy is the Prime Minister of Australia.
- Bitch in Sheep's Clothing: See the Reasonable Authority Figure subversion below.
- Disproportionate Retribution: He wanted Bart to be kicked with a giant boot over a stupid phone call.
- Lazy Bum: He's introduced lounging naked on a floating tire in a lake, rather than doing his job.
- Monster of the Week: Only appears (besides a picture cameo in "Holidays of Future Passed") in "Bart Vs. Australia" in which he is the main antagonist.
- President Evil: Or Prime Minister Evil in this case.
- Reasonable Authority Figure: Subverted. He seems perfectly fine accepting Bart's apology, until he has him arrested for an additional punishment, the booting, because "A mere apology would be a bit empty".
- Voiced by: Susan SarandonDebut: "Homer vs. Patty and Selma"
A Springfield Elementary School employee, who teaches the school ballet class.
- Voiced by: Mandy PatinkinDebut: "Lisa's Wedding"
A British student who becomes engaged to Lisa 15 years in the future, but after he insults her family, she breaks their engagement off.
- Always Someone Better: Reads faster than Lisa.
- Belligerent Sexual Tension: With Lisa. At first, the two quarrel over a book in the library, but the pair eventually fall madly in love.
- Bitch in Sheep's Clothing: He lets slip that after the wedding he plans for them to return to England and never see Lisa's family again.
- Foil: He's this to Mr. Bergstrom from "Lisa's Substitute". At first glance, they're both everything Lisa wants from a companion: witty, intelligent, cultured, sensitive, putting her at odds with her seemingly oblivious father Homer. But while Mr. Bergstrom helps Lisa understand that Homer does love her, Hugh tries to cut him out of her life, which makes Lisa realize that he doesn't really care about her.
- Gentleman and a Scholar: While at first he seems to be this, it's subverted at the end of the episode, revealing him to be a Jerkass.
- Stiff Upper Lip: His only real reaction to the trouble he faces at Homer's hands? "This is all quite trying."
- Debut: "The Springfield Connection"
Jericho is the jeans counterfeit who helped Herman illegally sell counterfeit jeans.
- Debut: "Lemon of Troy"
Shelby is a boy and apparent bully who lives in Shelbyville.
- Evil Counterpart: To Bart.
- Identical Stranger: He looks similar to Bart, with the exception of his hair, his pants, and the color of his hat.
- The Rival: To Bart, even for one episode.
- Debut: "Lemon of Troy"
- Determinator: Maintains his glare on the Springfieldians even as his eyes water and keeps shaking his fist ineffectually as they retreat.
- The Ditz: Like Homer.
- Evil Counterpart: To Homer, naturally.
- Evil Gloating: Eats one of the stolen lemons in front of Homer. His face puckers up.
- Meet Your Early Installment Weirdness: Sounds like Walter Matthau, a la early Homer.
- Unnamed Parent: His name is not revealed.
- Debut: "Lemon of Troy"
- Evil Counterpart: To Jebediah Springfield.
- Namesake Gag: You'd think Shelbyville got named after somebody called "Shelby". Well, you'd be wrong.
- We Used to Be Friends: Jebediah Springfield wanted a town devoted to chastity, abstinence, and a flavorless mush called "root-marm", whereas Manhattan thought they'd establish a town where people could marry their own cousins (the thought of which sickened Springfield). They swiftly became foes, extending their rivalry to the towns they each started.
- Debut: "King-Size Homer"
The pig Homer imagines in "King-Size Homer" during his imagination of his weight goal.
- No Celebrities Were Harmed: He is based on Cary Grant. Word of God even wanted Grant to play the pig until they remembered he'd been dead for years.
Colonel Leslie "Hap" Hapablap
- Voiced by: R. Lee ErmeyDebut: "Sideshow Bob's Last Gleaming"
An Air Force officer.
- Incredibly Lame Fun: Thinks box-kites are interesting. The audience disagrees.
- Large Ham: Being voiced by R. Lee Ermey will do that to you.
- Shout-Out: His entire character is one to Gunnery Sgt. Hartman from Full Metal Jacket, right down to being voiced by the same man who played him.
Detective Don Brodka
- Voiced by: Lawrence TierneyDebut: "Marge Be Not Proud"
The store detective at Try-N-Save. He catches Bart stealing a video game (Bonestorm) from the Try-N-Save.
- The Dreaded: Bart spends the entire episode scared of returning to the Try-N-Save store because of him.
- Inspector Javert: He catches Bart immediately, but doesn't see Jimbo and Nelson shoplifting. And it's probably not the first time.
- Jerkass: He has every right to be pissed about Bart's shoplifting, (attempt to) notify his parents, and ban him from the store... but when Bart and his family come back to get their picture taken, Brodka could have at least waited until their picture was done before he chastises the boy again. But he doesn't, and the picture shows a husky arm grabbing Bart.
- Debut: "Marge Be Not Proud"
A Brazilian actress who is the main presenter of the children's television programme, Teleboobies.
- The Capital of Brazil Is Buenos Aires: A minor case. She has an Aztec/Incan-sounding name despite being Brazilian.
- The Bus Came Back: Her debut is a no-speaking scene in "Marge Be Not Proud" when Krusty the Clown introduces a few people for his "Krusty Kinda Christmas" holiday special. She returns six seasons later (with a major role) in "Blame It on Lisa", where she is the host of a Brazilian children's television show named Teleboobies, which amuses Bart.
- Gag Boobs: In her show Teleboobies, she presents educational concepts using... her boobs. For example, Xoxchitla demonstrates the difference between clockwise and anti-clockwise, by shaking her torso and twirling tassels attached to her breasts.
- Latino Is Brown: Averted. She is a fair-skinned blonde, just like her real life inspiration seen below.
- Ms. Fanservice: Especially in "Blame It on Lisa" where she wears very revealing outfits (the most iconic is a low-cut pink leotard that shows off her quite ample cleavage).
- No Celebrities Were Harmed: She is a parody of Xuxa, an actress and TV show host from Brazil.
- Voiced by: Donald SutherlandDebut: Lisa the Iconoclast
The head of the Springfield Historical Society.
- Alliterative Name: Hollis Hurlbut.
- The Comically Serious: When Lisa jokes about having "Chester A. Arthritis", he only says "You have arthritis?".
- Poke the Poodle: After Lisa learns the truth about Jebediah Springfield, he immediately bans her, her future children, and her future children's children from the historical society... for three months.
Chester J. Lampwick
- Voiced by: Kirk DouglasDebut: "The Day the Violence Died"
The original creator of Itchy, and father of cartoon violence.
- Jerkass: He has a repeated habit of doing services in exchange for food, only to never finish them, claiming the food was "lousy".
- Rich in Dollars, Poor in Sense: In The Movie, he's seen as part of the mob sporting his bum rags, implying he's lost his fortune.
MacArthur "Mac" Parker
- Voiced by: Jeff GoldblumDebut: "A Fish Called Selma"
Troy McClure's agent.
- Voiced by: Christina RicciDebut: "Summer of 4 Ft. 2"
A girl who vacationed to Little Pwagmattasquarmsettport with her family.
- Voiced by: Albert BrooksDebut: "You Only Move Twice"
The president of the Globex Corporation, which includes a rival nuclear power plant. He tried to entice Smithers with an offer to switch jobs, and when Smithers turned it down, the same offer was quickly made to the next longest serving employee of the Springfield plant: Homer. As a boss, he's everything Burns is not: friendly, outgoing, hip, and concerned about his employees. He's also a Bond villain. Easily one of the most popular one-off characters.
- Affably Evil: Polite, benevolent to his employees to the point that they're his number two concern (number one being his schemes) and all in all a great guy to hang around with. He's also a supervillain.
- Anti-Villain: Despite wanting to Take Over the World, he's genuinely an Affably Evil Benevolent Boss, he's a friend instead of an enemy to the Simpsons, and it's implied that his successful East-Coast-takeover is actually a benevolent dictatorship at worst.
- Ax-Crazy: Especially in the episode's climax.
- The Bad Guy Wins: Successfully takes over the East Coast. Though given his personality it may not be too bad.
- Beard of Evil: He has a beard, and he is evil.
- Benevolent Boss: Very much so. To the point that even after Homer leaves, Scorpio tells him to call if there's anything he needs, and Scorpio even sends him a gift that will hopefully help Homer work up to his dream of owning the Dallas Cowboys. (Although Homer is rather disappointed at only getting the Denver Broncos.)
- Better Living Through Evil: What he promises, although he may not tell you about the evil bit.
- Beware the Nice Ones: For all that he is one of the greatest guys around, he did blow up a bridge just to prove a point to the UN, and has a man shot repeatedly. And he builds a giant laser cannon, with the apparent intention of using it on France.
- Cloud Cuckoolander: For some reason he keeps (unpackaged) sugar and cream in the pockets of his pants.
- Corrupt Corporate Executive: All benevolent traits aside, he's still seeking to use his business to advance his plan for world domination.
- Doomsday Device: Which he uses to blow up a bridge in New York City as part of his threat against the UN.
- Evil Laugh: Indulges in one when he breaks out his flamethrower, although his laugh is close enough to normal that it can be mistaken for a guy in the middle of having a really good time.
- Evil Genius: Damn, the guy's smart.
- Evil Virtues: We may as well add the whole list.
- Just the First Citizen: Claims to dislike being called boss or anything that elevates himself above others.
- Karma Houdini: Gets away scot-free, though he's just so Affably Evil that you're probably rooting for him anyway.
- Kill It with Fire: Shows a real enthusiasm for using a flamethrower...
- Laughably Evil: He's so damn polite and hilarious, even when trying to murder a James Bond Captain Ersatz or fighting off troopers with a flamethrower.
- Motor Mouth: Talks really fast.
- Mundane Solution: When the James Bond Captain Ersatz escapes from a Death Trap, Scorpio has him shot a few dozen times by armed guards.
- Resignations Not Accepted: Averted. When Homer comes to him in the middle of an assault by the US Military to talk about his family isn't happy there and wants to move back to Springfield, Scorpio advises Homer to do what's right for his family and only says "On your way out, if you could kill somebody, it would help me a lot."
- Slave to PR: Likes moccasins. Unless Homer doesn't like them. In which case the moccasins can get lost so that Scorpio appears relatable to his newest employee.
- Take Over the World: According to his Villain Song, it's one of his two obsessions. The other is the health of his employees. By the end of the episode, he's apparently taken over the East Coast of the United States.
- Villain of Another Story: A bizarre example; Hank never antagonizes Homer and his family despite being a villain.
- Villain Protagonist: The perspective is shared with Homer, his Unwitting Pawn.
- Voiced by: Paul WinfieldDebut: "The Homer They Fall"
A crooked boxing promoter who once represented Moe when Moe was a fighter. When he hears that Moe is involved with the boxing game again, managing Homer, he sets up a match between Mike Tyson analogue Drederick Tatum and Homer.
- Captain Ersatz: Of boxing promoter Don King, complete with all the baggage that goes along with that. Lampshaded when Homer outright says he looks like Don King and is exactly as rich and famous. Paul Winfield, who voiced Sweet, played King in the 1995 TV movie Tyson.
- Delusions of Eloquence: "This is an egregious miscarriagement of taxitude!"
- Expy Coexistence: Despite being an obvious expy of the infamous boxing promoter Don King (a fact which Homer very pointedly lampshades), both men apparently exist in the universe of The Simpsons.
- Fat Bastard: Is on the portly side.
- Improbable Hair Style: One that resembles Don King.
- Jerkass: The Simpsons Guide to Our Favorite Family describes him as having no evident soul. Drederick Tatum was touched seeing Moe flying Homer out of the ring, and asks Lucius if he'd do the same for him. Lucius says "Absolutely, I would.", chuckling awkwardly before bluntly telling Tatum to get in their van.
- Pet the Dog: Even as he's castigating and insulting Moe, he still gives him a check for Homer's last fight.
- Voiced by: Rodney DangerfieldDebut: "Burns, Baby Burns"
The son of Montgomery Burns and Lily Bancroft.
- Big Fun: Much to his father's dismay. His intense causality, uncouth manner, lack of intelligence and love of drinking means that he has many things in common with Homer Simpson and they become good friends.
- Book Dumb: He does poorly on an aptitude test ("He spelled 'Yale' with a six."), but is quite worldly.
- Disappeared Dad: Mr. Burns is his.
- Ink-Suit Actor: He basically IS Rodney Dangerfield with Mr. Burns' crooked nose.
- Put on a Bus: After Burns disowns him, Larry returns home, realizing he had not told his wife and children where he was for a week.
- Debut: "Bart After Dark"
An entrepreneuse and the proprietoress of a burlesque house in Springfield called "La Maison Derrière".
- Broken Glass Penalty: For Bart's accidental destruction of her Gargoyle, she makes him do community service at her Burlesque House.
- Cool Old Lady: Doesn't flinch at Marge's attempts to intimidate her.
- Deadpan Snarker: Completely unfazed by Marge taking out a chunk of her house.
- Delayed Reaction: It takes her a while to notice Homer's only wearing a grocery bag.
- Miss Kitty: Even though the show is set in modern America, the matron of the house plays this trope completely straight and makes Marge look foolish by comparison.
Jimmy the Scumbag
- Debut: "Lisa's Date with Density"
A small-time crook.
- The Quiet One: According to the Simpsons episode guide, he doesn't say anything without his lawyer around.
- Debut: "Hurricane Neddy"
Ned Flanders' childhood psychologist.
- Large Ham: "In the den? May God have mercy on us all!"
- Nice Job Breaking It, Hero!: Fixed Ned's anger problems, but at the cost of making him incredibly repressive.
- Voiced by: Johnny CashDebut: "El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)"
Homer's Spirit Guide (also referred to as "The Space Coyote" or Johnny) is a talking coyote whom Homer meets in a chili-induced hallucination. Homer calls him "Wolfy".
- Maybe Magic, Maybe Mundane: He and the entire experience could have just been the result of Homer consuming "Guatamalan insanity peppers".
- My Instincts Are Showing: Starts chewing on Homer's leg. He is a coyote, after all.
- Non-Standard Character Design: Much more angular than regular characters.
Frank Ormand, the Pretzel Man
- Voiced by: Jack LemmonDebut: "The Twisted World of Marge Simpson"
The owner of the Pretzel Wagon.
- Killed Off for Real: In a car crash, one that also took the executor of his estate with him.
- Voiced by: Maggie RoswellDebut: "Simpsoncalifragilisticexpiala(Annoyed Grunt)cious"
Shary Bobbins was the Simpson family's magical nanny.
- Amicable Exes: A one-sided version toward Groundskeeper Willie.
- Cruel and Unusual Death: Sucked into an airplane engine.
- Deconstruction: Of the Magical Nanny archetype. While she is briefly successful in cleaning up the Simpsons, she can't stop them from quickly sliding back into their slovenly ways, and get them to care about changing their ways.
- Expy: Of Mary Poppins, though she vehemently denies it.
- Screw This, I'm Out of Here!: Eventually, when the Simpsons admit they're not going to change their ways, she decides to leave.
- Voiced by: Tress MacNeille (normal voice), Dan Castellaneta (as Itchy), and Harry Shearer (as Scratchy)Debut: "The Itchy & Scratchy & Poochie Show"
The voice actress who plays Itchy and Scratchy.
- Cross-Dressing Voices: An In-Universe example. She's a woman who voices two male characters.
- Mean Character, Nice Actor: Bellamy is a very pleasant woman who voices the violent, titular duo of Itchy and Scratchy who always go at it. Itchy, in particular, is a real Jerk Ass who always mutilates Scratchy in the most gruesome ways imaginable for little to no reason.
- Nice Girl: She's very friendly and is the only one to stand up for Homer when the crew wants to kill his character off permanently.
- No Celebrities Were Harmed: June is inspired by and named after the late voice actress June Foray.
- Debut: "The Itchy & Scratchy & Poochie Show"
A college-aged cool guy who stays at the Simpsons home temporarily.
- But Now I Must Go: Leaves as suddenly as he appeared, moving into an apartment with "Two sexy ladies".Bart: Tough break, dad. I guess people just weren't ready for Poochie. Maybe in a few years...
Roy: (walks in with a letter and a suitcase in his hands) Good news, everybody! I'm moving into my own apartment with two sexy ladies!
Marge: Then I guess this is goodbye, Roy. Maybe we'll see you in a few years.
- Remember the New Guy?: Spoofed. He's introduced like he's always been present right after Lisa comments that adding new characters to a show always seems to be a desperate attempt at boosting low ratings.
- Voiced by: John Waters
- Ink-Suit Actor: He looks just like John Waters, only with a squigglier mustache because it's easier to animate.
- Voiced by: David Hyde PierceDebut: "Brother from Another Series"
Sideshow Bob's brother.
- Always Someone Better: Bob was this to him, in his second appearance he is referred as Laertes to Bob's Hamlet.
- Arch-Enemy: To Lisa in the comics, even though he comes to care for her after realizing that they are similar.
- Ascended Extra: In the comics.
- Ax-Crazy: Unlike Bob, he isn't amazing at hiding it.
- Bitch in Sheep's Clothing: To the world, he comes across as a polite businessman with the best interests of the town and his company in mind. In reality, he's willing to murder the entire town by letting it be washed away, just so he can embezzle it.
- Cain and Abel: He's the Cain to Bob's Abel.
- Evil Is Petty: He's willing to destroy Springfield and everyone in it because Bob got to be Krusty's sidekick instead of him, though he says that officially he did it for the money.
- Eviler Than Thou: To Sideshow Bob.
- Faux Affably Evil: He is quite polite but in a rather fake way.
- Ivy League for Everyone: Went to Princeton. (Or, as Bob calls it, "clown college".)
- Jerkass: Worse than his brother.
- Knight of Cerebus: He certainly is an Up to Eleven version of Sideshow Bob.
- The Resenter: Jealous of Bob for being Krusty's sidekick.
- Vile Villain, Saccharine Show: Cecil is Sideshow Bob if he was more competent. He tried to kill two children and his own brother.
- Why Don't You Just Shoot Him?: Bart invokes this with him in an effort to buy himself more time. However, Cecil is too clever to fall for it and says that if anybody asks him, he'll lie about a more creative way of killing him. He then throws Bart off the dam.
- Voiced by: Dave ThomasDebut: "Homer vs. the Eighteenth Amendment"
A U.S. Treasury officer who was briefly sent to Springfield to uphold Prohibition after Bart got drunk in a live news report, which incited several women to force the city government to declare Prohibition.
- Expy: Of Elliot Ness, from The Untouchables. His name in the Latin American dub is "Elio Pez" to boot.
- Failed a Spot Check: While interrogating Comic Book Guy, he completely ignores Homer walking by, dragging along a wagon filled with barrels of beer.
- Knight Templar: His solution to illegal shipments of alcohol being brought in by truck? Put up a wall that blocks the road into Springfield, causing a massive car accident. Banner actually smiles when he sees the results of this.
- The Stoic: He tries to laugh at one point, but can only produce a strained, hacking noise.
- Unexplained Recovery: He's launched from a catapult in "Homer vs. The Eighteenth Amendment", but appears alive and well as part of the mob in the movie.
- Voiced by: Sab Shimono
- Animesque: Homer drawn in an anime style.
- Identical Stranger: He looks almost exactly like Homer.
- Motif Merger: He's the combination of Matsamura Fishworks' and Tamaribuchi Heavy Manufacturing Concern's logos merged together.
- Nice Job Breaking It, Hero!: One of the comics has him cleaning a manga artist's office, including wiping his drawings blank.
- Debut: "Homer's Enemy"
A hard worker and Homer's self-proclaimed nemesis.
- Absurdly Youthful Father: He is stated to be 35 in "Homer's Enemy" but his son is a grown man as well, implying that he had sex with prostitutes as a teenager.
- Audience Surrogate: The creators intention of creating him in the first place.
- Back from the Dead: Although he supposedly dies after being electrocuted, The Simpsons: Tapped Out reveals that he was simply in a coma and got buried alive. He rises from his grave and resumes his life throughout a series of quests. This storyline is seemingly continued in a 2015 issue of Simpsons Comics, in which Homer passes by Grimes at the power plant as if he never "died" at all.
- Berserk Button:
- Homer is a big fat button.
- Also he doesn't like to be called "Grimey". Or "Stretch".
- Born Unlucky: Nothing ever goes his way, ever.
- Butt-Monkey: Very much so. He had to struggle his whole life and only makes the bare minimum while Homer gets to live a decent life despite his lack of intelligence.
- Continuity Nod: Nearly every episode that includes Grimes and/or his tombstone expects the viewer to have seen his debut episode.
- Determinator: He majored in nuclear physics despite his complete lack of a formal education, and minored in determination.
- Driven by Envy: His hatred towards Homer increases even after the latter attempts to reconcile with him, due to Homer showing his achievements like going into space, winning a Grammy, going on tour with the Smashing Pumpkins, and befriending Gerald Ford. Frank is of course upset that someone like Homer could do all those things when he himself got nothing from his hard work.
- Embarrassing Nickname: Homer nicknames him "Grimey", which he hates. It even appears on his tombstone.
- Enraged by Idiocy: To the point that Homer's stupidity drives him insane at the end of the episode.
- The Everyman: Frank Grimes is supposed to represent the viewer in this episode. A man that appears in no way remarkable who never got any breaks and had to work hard every day of his life with little to no rewards.
- Expy: Frank is based on Michael Douglas' character Bill Foster from Falling Down. They both wear glasses, white shirt, black tie, black pants. They both even have the same haircut.
- Fourth-Wall Observer: His punishment in Hell is to watch every Simpsons episode in order.
- Freak Out: After Homer wins the children's model power plant contest, he flies completely off the deep end and begins acting like a deranged caricature of Homer's worst traits. This leads him to grab a set of dangerous electrical cables without safety gloves, bringing a swift end to his life.
- Freudian Excuse: The utterly miserable life he's led would make anyone unstable.
- The "Fun" in "Funeral": People laughed during his funeral due to Homers disrespectful sleeping. Even Reverend Lovejoy joined the laughter.
- Giving Up on Logic: Angrily did this after his Sanity Slippage and began imitating Homer's stupid antics. It took him about a minute to get himself killed.
- Grave Humor: His grave is often seen with his hated nickname from Homer "Grimey" on it. In one episode his grave has "(Homer's Enemy)" written on it.
- Hilariously Abusive Childhood: His backstory describes a ridiculous amount of misfortune that he's had to overcome.
- Hoist by His Own Petard: He tried to trick Homer into joining a plant-modeling contest for kids, and Homer won, much to his dismay.
- In-Series Nickname: "Grimey".
- Jerkass: Even though Homer not only tries to make it up to Grimes but actually tries to listen to his advice (albeit in a half-assed fashion), Grimes still antagonizes him and tries to humiliate him in front of everyone.
- Jerkass Has a Point: He had a terrible life and had to work hard to get his job. He sees Homer, quite rightly, as being successful despite being an incompetent, lazy slob; making a mockery of all his suffering and efforts. This would enrage anyone.
- Naïve Newcomer: A new employee and a generally normal person (as the Audience Surrogate) who still doesn't know how things work in The Simpsons world and how to deal with people like Homer every day.
- Negative Continuity:
- His tombstone has different inscriptions from episode to episode. These include "Grimes", "Frank Grimes", "Frank 'Grimey' Grimes", and "Frank Grimes (Homer's enemy)".
- This occurs even in his introductory episode, where he is explicitly shown living in a house when he receives his degree, but he later claims to live in a studio apartment above (and below) two bowling alleys.
- Nerd Glasses: Wears a pair.
- No Respect Guy: Hes smarter and more qualified than his co-workers, especially Homer, but never got any respect. People even laughed during his funeral.
- Not So Above It All: He has a illegitimate son, because he apparently liked hookers (according to episode "The Great Louse Detective").
- Not So Different: In a twist of Dramatic Irony, for all of Grimes' resentment towards Homer, he and Homer have pretty similar to each other. Both of them have troubled childhoods suffering from Parental Abandonment, struggle to make a living in their adulthood, and harbour an intense jealousy towards someone for being more successful in life than they could (i.e. Flanders for Homer, Homer for Grimes).
- Only Sane Man: He's the only person to point out that Homer shouldn't be remotely successful, popular, or even alive given his behavior, and is driven mad when no one else notices or cares. Even the universe is against him, as he's trying to apply real-world logic to a cartoon world. Oakley and Weinstein summed it up best by referring to Grimes as what would happen if someone from the real world met Homer.
- Parental Abandonment: Literally. The TV news summary of his life shows them putting four-year-old Frank out of their car in the middle of the road and driving off.
- Promoted to Opening Titles: His grave appears in it since 2009.
- "The Reason You Suck" Speech:Frank: I'm saying you're what's wrong with America, Simpson. You coast through life, you do as little as possible, and you leech off of decent, hardworking people like me. Heh, if you lived in any other country in the world, you'd have starved to death long ago.
Bart: He's got you there, dad.
Frank: You're a fraud. A— a total fraud. (walks out, pokes his head back round the doorway, and speaks to Marge and the kids) It was nice meeting you.
- The Resenter: To Homer.
- Sanity Slippage: He eventually has a breakdown and starts impersonating Homer, whose consequence-free stupidity drove him to this point. This ends when he has a moment of genuine stupidity and electrocutes himself. Unfortunately the same rules don't apply to Grimes and this mistake costs him his life.
- Springtime for Hitler: Frank tricks Homer into entering a power plant designing contest for kids as an attempt to show the world what an idiot Homer is. Homer ends up winning, and Frank's sanity utterly disappears after this.
- Surrounded by Idiots: The whole premise of his episode is watching a normal person try to cope in Springfield.
- This Loser Is You: Grimes is said to be a representation of what a realistic person, who was a hard-working, working-class employee, would be like if they got the misfortune of working with Homer or living in Springfield.
- X-Ray Sparks: His death.
- Yank the Dog's Chain: At first, it looks like his hard work is about to pay off when Mr. Burns decides to make him Executive Vice President of the plant...only to give the position to a dog instead and just throw Grimes into Sector 7G. Things get progressively worse from there.
- Voiced by: Gailard SartainDebut: "The Simpsons Spin-Off Showcase"
"Chief Wiggum's PI's" Arch-Enemy that appears in the "Wiggum, P.I." segment of the non-canon episode "The Simpsons Spin-Off Showcase".
- Acrofatic: Big Daddy rather handily escapes from the parade while being chased by Wiggum and Skinner.
- Affably Evil: He may have kidnapped Ralph but he was nice enough to take him to "Mardi Gras" and buy him an ice-cream.
- Calling Card: Played with near the beginning. While Wiggum and Skinner are discussing about their current situation, a skull is thrown through the window, and the duo realize they have an enemy. Later on, another skull is left behind after Ralph is kidnapped. Cue Skinner: "Big Daddy's trademark calling card... it's right here inside the skull."
- Chair Reveal: Played with as we see Big Daddy run into his office and get into position so he can pull off this trope when Wiggum comes in shortly after.
- His Name Really Is "Barkeep": Charles Daddy.
- This Is Gonna Suck: Big Daddy has this reaction when he is spotted by Wiggum and Skinner and has to run.Big Daddy: Lord have mercy, how I wish I weren't so fat.
- Villain: Exit, Stage Left: Parodied in Chief Wiggum P.I., in which Big Daddy swims away through the river... slowly.Skinner: He's gradually getting away, Chief.Wiggum: Ah, let him go. I have the feeling we'll meet again, each and every week. Always in more sexy and exciting ways.
- Villains Out Shopping:"New Orleans is my town. I got interests, and I ain't talkin' about stamp collecting, though I do find that extremely interesting."
- Voiced by: Willem DafoeDebut: "The Secret War of Lisa Simpson"
The commandant of Rommelwood Military School, attended by Bart and Lisa.
- Everyone Calls Him "Barkeep": He is just called The Commandant.
Sgt. Seymour Skinner
- Voiced by: Martin SheenDebut: "The Principal and the Pauper"
The real Seymour Skinner. He was a sergeant in the US Army, but got caught by the enemy and spent five years in a POW camp, and was then sold to a shoe-producing company in China. After the company closed, he came back to Springfield, only to find out that Armin Tamzarian basically lived his life for the entire time he was gone. He took back his place, but because his attitude made the townspeople uncomfortable, he was forced to leave (read: tied to a train and basically kicked out).
- A Father to His Men: To Tamzarian, which was partly why Tamzarian decided to assume Skinner identity.
- Foil: Represents everything the representing Skinner fails to be, having a strong backbone and sense of pride and ethics (if naively so). He cares about the school faculty teaching its children properly, and thinks independently from his mother, whose shrill browbeating completely fails to beckon him. Expectedly everyone in Springfield soon decides they like him a lot less than the fake Skinner.
- Put on a Bus to Hell: Put on a train and never seen again. His entire existence is forbidden from being mentioned again, under penalty of torture. In Real Life both fans and some writers pretend this episode never happened.
- Replacement Scrappy: In-Universe. He takes Armin's place as principal while Armin leaves town. However, despite the real Skinner being a nice and reasonable fellow, the other Springfield citizens decide to kick him out of town (even his mother, who preferred the doormat Armin to the independent Seymour) and get a judge to order everyone never to speak of this again under penalty of torture because... they preferred the old Skinner.
- Retcon: His appearance completely changes Skinner's backstory. However Judge Snyder grants Tamzarian Skinner's "name, and his past, present, future, and mother", and decrees that no one will mention his true identity again under penalty of torture. The only time this rule has been broken since was when Lisa refers to Principal Skinner as "Principal Tamzarian" when he witnesses her name her new cat Snowball II instead of Snowball V in "I, (Annoyed Grunt)-Bot".
- Un-person: Enforced after he was sent away.
Bart's Kindergarten Teacher
- Voiced by: Maggie RoswellDebut: "Lisa's Sax"
Bart and Milhouse's kindergarten teacher.
- Apathetic Teacher: By far the most deflated and cynical member of Springfield Elementary, which is saying a lot. She teaches her class in a perpetually bored and contemptuous tone, and pulls no punches in telling children like Bart they have no hope in life. That's right, she is the reason that Bart is the troublemaker that he is today!
- Create Your Own Villain: She is Springfield Elementary's apathetic deadbeat system at its worst, and is the one that embitters Bart into the faculty's biggest bane of their lives.
- Deadpan Snarker: She appears to be a cynical and sarcastic person.
- Evil Counterpart: She's Miss Hoover had she totally stopped caring, right down to the same voice actor.
- Jerkass: She is the one initially responsible for making Bart feel miserable and unable to fit in at school, which leads him to seek attention through mischievous behaviour.
- Karma Houdini: Ironically about the one member of Springfield Elementary that Bart never victimises onscreen.
- No Name Given
- Small Role, Big Impact: Her crushing of Bart's enthusiasm at an early age led to him becoming an attention-seeking delinquent.
- What Happened to the Mouse?: She is never seen outside the flashback of this episode, with other teachers shown in the present day kindergarden faculty. Granted, given she was left teaching Bart in the form of a hellion, and her clear antipathy for her job in the first place, it's not inconceivable that she quit within that time period.
Cooder and Spud
- Debut: "Bart Carny"
A father-son carny duo.
- Jerk Ass: After spending a day with the carnies, they take the Simpsons' home and the Simpsons have to live in Bart's treehouse.
- Voiced by: Rod SteigerDebut: "Simpson Tide"
The captain of the Springfield Naval Reserve submarine during its annual war games.
- Expy: Tenille is based on Captain Frank Ramsey, a character from the 1995 film Crimson Tide, who was portrayed by Gene Hackman. His episode's title was derived from the same movie.
- Horrible Judge of Character: He takes an instant shine to Homer because of misunderstanding of naval jargon. He later invites Homer to eat with him and, misunderstanding what he was actually saying, concludes Homer's views on peace are the same as his and thus Homer is "like the son I never had." He leaves Homer in command while he goes to investigate the torpedo tube. It ends up costing him his life.
- Terse Talker:Tenille: I'm a man of few words. (beat) Any questions?
- Voiced by: Steve MartinDebut: "Trash of the Titans"
Springfield's sanitation commissioner.
- Butt-Monkey: He is tormented by Homer and the townspeople who fall for Homer's insanity. He gets his revenge.
- Cassandra Truth: He tries to warn the townsfolk that Homer's promises are unworkable, but they just brush him off.
- Deadpan Snarker: Inevitable when it's Steve Martin.
- Guilt by Association: Homer's vendetta with Patterson stems from two of his thuggish employees skipping his yard on duty and then attacking him and cutting off their services after he complains. While this was poor choice of staff on Patterson's side, rather than simply protest about the incident, Homer being Homer, decides to pick a fight with the guy in charge.
- I Warned You: After Homer inevitably screws up, Springfield calls him back, but he's got some choice words:Ray: Oh gosh. You know, I'm not much on speeches, but it's so gratifying to (sighs) leave you wallowing in the mess you've made. You're screwed, thank you, bye.
- Ignored Expert: Ray Patterson was smart enough to see that Homer basically has no clue what being sanitation commissioner is all about.Ray: All right, fine. If you want an experienced politician, vote for me. But if you want to believe a bunch of crazy promises about garbagemen washing your cars and emptying your kitty litter, then by all means, vote for this sleazy lunatic.
- Ink-Suit Actor: He looks just like Steve Martin.
- Only Sane Man: Compared to many of Springfield's residents, Ray Patterson is one of the more 'sane' characters; hard working and committed to his job.
- Screw This, I'm Outta Here!: After Homer was fired for encouraging other cities to dump their garbage in the abandoned mine (in order to solve the budget crisis), Patterson got his job back, but he refused to help clean up the town instead choosing to leave them "wallowing in the mess you have created".
Brad and Neil
- Debut: "King of the Hill"
Brad and Neil are two spokesmen for Powersauce.
- Voiced by: Lisa KudrowDebut: "Lard of the Dance"
A popular "grown-up" girl in Lisa's class. Lisa becomes very jealous of her, because Alex steals her friends.
- Alpha Bitch: Definitely the alpha part, though she doesn't really do anything worse than be childishly rude. Although her cameo in "Father Knows Worst" plays it painfully straight.
- Not So Above It All: At the end of the episode, turns out Alex isn't totally above having a greaseball fight for fun.
- Valley Girl: She uses Valley Girl slang, which is mainly used by teenage girls.
- Verbal Tic: "He-LOO!".
- Wise Beyond Their Years: Or so she thinks.
Seth and Munchie
- Voiced by: Martin Mull and George CarlinDebut: "D'oh-in' in the Wind"
Mona Simpson's hippy friends in the 1960s.
- Voiced by: Mark HamillDebut: "Mayored to the Mob"
A professional bodyguard trainer who owns and operates Leavelle's Bodyguard Academy.
- Fat, Sweaty Southerner in a White Suit: Judging by his accent, he seems to be from Texas.
Amber Pai Gow (Simpson)
- Voiced by: Pamela HaydenDebut: "Viva Ned Flanders"
Homer's Vegas wife.
- Accidental Marriage: With Homer in "Viva Ned Flanders".
- The Bus Came Back: She and Ginger comes back in "Brawl In The Family". Homer attempts to annul his marriage to Amber, but it is upheld under Nevada law. To get her out of their lives, the Simpson family tricks Amber into marrying Grampa and agreeing to forsake her vows to Homer.
- Killed Offscreen: In "Jazzy and the Pussycats", it is revealed that Amber died of an overdose at a theme park in front of a sign warning guests not to stand up on a roller coaster. Her funeral is held in Springfield and attended by the Simpsons.
- Debut: "Viva Ned Flanders"
Ned's Vegas wife.
- Accidental Marriage: With Ned Flanders in "Viva Ned Flanders".
- The Bus Came Back: She and Amber came back in "Brawl In The Family". Unlike Homer, Ned reluctantly allowed Ginger into his home.
- Screw This, I'm Outta Here!: Ginger left him because Ned, Rod and Todd were too good (they flushed her cigarettes down the toilet and sang all day).
- Voiced by: Fred WillardDebut: "Sunday, Cruddy Sunday"
A travel agent who takes Homer and his friends to the Super Bowl.
- Mythology Gag: He's named for classic Simpsons writers Wallace Wolodarsky and Jay Kogen, who'd written for the show during the first 4 seasons, including the original "Treehouse of Horror" special, "Bart The Daredevil", and "Lisa the Greek", which is also about the Super Bowl.
- Debut: "Maximum Homerdrive"
A man whom Homer meets at The Slaughterhouse. He's a trucker.
- Big Eater: He's one of only 2 people to ever finish the Sir Loin-A-Lot steak (the other being Tony Randall).
- Death by Gluttony: The second time doesn't work out so well for him.
- Voiced by: Isabella RosseliniDebut: "Mom and Pop Art"
The owner of an art gallery.
- Voiced by: Michael McKeanDebut: "Monty Can't Buy Me Love"
The radio shock jock who hosts "Jerry Rude and the Bathroom Bunch".
- No Celebrities Were Harmed: He's a clear parody of Howard Stern.
- Voiced by: George TakeiDebut: "Thirty Minutes Over Tokyo"
A Japanese game show host who has a game show called "Super Happy Smile Time Family Wish Show", which the Simpsons compete on to get tickets back to Springfield.
- Sadist: He clearly enjoys the suffering of the contestants.
- Voiced by: Ed AsnerDebut: "Guess Who's Coming to Criticize Dinner?"
The editor of the Lifeways section of the Springfield Shopper.
- Working with the Ex: He used to be married to the retiring food critic.I'd hate to be married to her... I mean again.
- Voiced by: Garry MarshallDebut: "Guess Who's Coming to Criticize Dinner?"
The owner of the Springfield City Zoo.
Meathook and Ramrod
- Debut: "Take My Wife, Sleaze?"
Members of the Hell's Satans, a motorcycle gang.
- Voiced by: Tim RobbinsDebut: "Grift of the Magi"
The president of Kid First Industries.
- Voiced by: Don CheadleDebut: "Faith Off"
A faith healer. He holds a show named Brother Faith's Revival.
- Debut: "Faith Off"
A football player for Springfield University.
- A Degree in Useless: If he had to give up his football career, he'd have to fall back on his degree in communications.
- Voiced by: Shawn ColvinDebut: "Alone Again, Natura-Diddily"
The twenty-seven year old lead singer of Kovenant, a Christian rock band.
- Replacement Love Interest: Subverted. First she appears to be a possible new love interest for Ned Flanders, but she leaves soon after Ned attempts to mold her in the image of his deceased wife Maude by cutting her hair to look like Maude's.
Ak and Q'toktok
- Debut: "Missionary: Impossible"
Natives from a South Pacific island.
- Voiced by: Pamela HaydenDebut: "Pygmoelian"
Titania is a bartender works at Juggernauts and Knockers. She's the runnerup in the "BeerTender of the Year" contest.
- Ascended Extra: In the comics. Aside from few cameos in the main comic, she appears in Bart Simpson Comics 31 where she, similar to Moe and Maggie, solves crimes with Baby Gerald.
- Bare Your Midriff: She wears a magenta Tank-top that reveals not just her deep cleavage, but also her midriff.
- Buxom Is Better: In the "BeerTender of the Year" contest she pulls out all the stops in using her "assets" to increase her chances of winning.
- Cheaters Never Prosper: She sleeps with Duffman so he'll let her win a beer-related contest. Too bad for her Duffman lied about that.
- Gag Boobs: One of major example in the series. She has extremely large breasts.
- Gainaxing: She uses this combined with her natural talents to her advantage in order to try and win.
- Ms. Fanservice: A sexy blonde girl and one of most buxom characters to ever appear in the show.
- Voiced by: Diedrich BaderDebut: "Kill the Alligator and Run"
A sheriff who lives in Florida who chases the Simpsons after they "kill" Captain Jack the alligator.
- Inspector Javert: The Sheriff is extremely harsh and nasty in his duties. In addition to arresting Homer (after he "kills" Captain Jack the alligator) he arrests Marge, Bart, Lisa and even Maggie even though he admits he didn't have to go that far.
- Reasonable Authority Figure: Subverted. During spring break the beer companies pay him to act nice, but for the rest of the year he becomes harsh and mean.
- Visual Pun: His neck is literally red.
- Voiced by: Parker PoseyDebut: "It's a Mad, Mad, Mad, Mad Marge"
Otto Mann's ex-fiancée.
- The Ace: Becky is a great cook, a painter, knows how to stage karate moves, kills her competition at a talent contest and foils a usurper.
- Always Someone Better: To Marge.
- Comedic Sociopathy: No-one even reacts at the revelation that she was trying to kill Marge.
- Cool Big Sis: She act like this in the Simpsons house, helping Lisa and Bart.
- Evil All Along: After Marge apologizes to Becky for mistrusting her, Becky does admit that she was trying to kill Marge, but backed out because although she found a good place to bury her, she couldn't choose a shovel at the hardware store.
- Mistaken for Murderer: Marge is convinced by her sisters Patty and Selma that Becky will attempt to seduce her husband Homer and kill her. When Marge claims that Becky's planning to murder her, this leads to her being labeled insane. Subverted when turns out Becky really was trying to kill Marge.
- Debut: "Insane Clown Poppy"
Krusty's long-lost daughter.
- The Bus Came Back: She reappears in "The Nightmare After Krustmas", a Christmas Episode in Season 28.
- Hereditary Hairstyle: She shares Krusty's cactus-style hairdo and the same hair color.
- You Gotta Have Blue Hair: Her hair is a shade of teal.
- Debut: "Insane Clown Poppy"
Sophie's mother, a female soldier whom Krusty had a one-night stand with during the Gulf War.
- All There in the Manual: Her name is revealed to be Erin in The Krusty Book of the Simpsons Library of Wisdom series.
- Berserk Button: As a result of her experience with Krusty, Erin came to hate clowns, and filled her apartment with artwork showing them being tortured and killed.
- No Name Given: She's never referred to by name in "Insane Clown Poppy", but it has since been revealed through The Krusty Book.
- Debut: "New Kids on the Blecch"
The man who recruited Bart, Milhouse, Nelson and Ralph into a boy band called the Party Posse. He was secretly working with the government to recruit people to join the navy by using subliminal messages in a music video.
- Bitch in Sheep's Clothing: He doesn't appear to be evil at first.
- Disproportionate Retribution: He decides to blow up Mad Magazine just because they wanted to do a spoof of the band. Even more, the boys themselves take the "insult" as a compliment.
- Louis Cypher: Parodied. His name isn't L.T. Smash, it's Lieutenant (Lt.)... L.T. Smash.
- Pyrrhic Villainy: L.T succeeds in blowing up the MAD building, however, the writers survive the explosion and are even sober now.
- Voiced by: Kathy GriffinDebut: "Bye Bye Nerdie"
- Androcles' Lion: Subverted. When Lisa sees her eating lunch alone, she goes over and introduces herself. Francine immediately punches her.
- The Bully: A female example. She is an interesting case, as it's revealed that she's a bully because she has an adverse reaction to the sweat that emanates from nerds. It's shown that this also affects Nelson (Lisa demonstrates by swabbing nerd sweat on boxer Dreaderick Tatum and Nelson compulsively begins beating him).
- Huge Schoolgirl: She is heavyset.
- Living Prop: She has made a few cameos throughout the series.
Dr. Joan Bushwell
- Debut: "Simpson Safari"
A renowned animal researcher who lives among the chimps.
- Bad People Abuse Animals: Joan Bushwell turns out to be guilty of this when it's revealed she's been using the chimps she's supposedly been researching to run a diamond mine within her refuge to make herself rich.
- Broken Pedestal: Lisa says that Joan Bushwell's research has really inspired her when they first meet. At the end of the episode, Lisa is disgraced by the revelation that she's actually using the chimps to run a diamond mine, and is the only one to leave Africa without any diamonds.
- No Celebrities Were Harmed: She's a spoof of Dr. Jane Goodall, who lives among the chimps to conduct her research.
- Sanity Slippage: Dr. Bushwell admits that she snapped due to crushing loneliness and greed."No! Don't put me away. I'll give you diamonds. Everybody wants diamonds. Diamonds will make everything all better. Diamonds! Diamonds!!!"
- Debut: "Trilogy of Error"
Linguo is a grammar-correcting robot created by Lisa for the science fair.
- Debut: "Children of a Lesser Clod"
A gymnastics instructor.
- Hair-Trigger Temper: "Lugash must go to anger management class. WORTHLESS...ANGER MANAGEMENT CLASS! I HATE IT SO MUCH!"
- No Celebrities Were Harmed: He is inspired by former U.S. gymnastics coach Béla Károlyi, who also has his own gym.
The Singing Hobo
- Debut: "Simpsons Tall Tales"
The Singing Hobo is a hobo who lives in a train carriage and swaps stories for sponge baths.
- Voiced by: Julia Louis-DreyfusDebut: "A Hunka Hunka Burns in Love"
The ex-wife of Snake Jailbird and the ex-fiancée of Mr. Burns.
- All Girls Want Bad Boys: She is attracted to "bad boys". She dumps Burns for her former boyfriendpretty criminal Snake Jailbird, causing much confusion for Mr. Burns: "I don't understand, Simpson! I'm a bad boy! I'm completely evil! I once blotted out the sun!".
- MayDecember Romance: She was dating Mr. Burns. She's in her late 20s or early 30s while he is probably over 100 years old.
- Voiced by: Delroy LindoDebut: "Brawl in the Family"
Gabriel is a council worker who is employed to keep the Simpson family together.
- Magical Negro: Homer thinks Gabriel is an angel, much to Gabriel's annoyance.
- "The Reason You Suck" Speech: Gabriel gives a very succinct, powerful one after telling Homer he has a lot of problems. It's also the only time he raises his voice:Homer: Which is society's fault because-Gabriel: It's your fault!
- Screw This, I'm Outta Here!: When he sees Homer's Vegas wife.Gabriel: Your seed should be wiped from the Earth!
- Voiced by: Ben StillerDebut: "Sweets and Sour Marge"
The owner of Motherloving Sweets and Sugar Company.
- Corrupt Corporate Executive: The very concept of corporate ethics is completely alien to him.
- Jerkass: He is a total jerk.
- Sarcasm Mode: His "agreeing" to Marge's suggestions.
- Unfortunate Names: He claims that his surname was originally Hitler.
- Voiced by: Reese WitherspoonDebut: "The Bart Wants What It Wants"
The daughter of famous actor Rainier Wolfcastle.
- Operation: Jealousy: Develops a crush on Bart, but he is Oblivious to Love so she tries to date Milhouse to make him jealous.
- Rescue Romance: She develops a crush on Bart when he saves her from two bullies.
- Spoiled Sweet: Rich and pampered, but quite nice.
- Zettai Ryouiki: In the beginning of "The Bart Wants What It Wants", when Bart saves her from bullies.
- Voiced by: Olympia Dukakis.Debut: "The Old Man and the Key"
Zelda is the elderly woman with whom Abe falls in love.
- Bitch in Sheep's Clothing: She only dates Grandpa because he's regained his driver's license.
- Gold Digger: Only wants guys with cars.
- Humiliation Conga: She is publicly humiliated in Branson, Missouri when Abe and Charo call her a hoochie in front of a huge crowd. He even gets the crowd to chant "Hoochie, Hoochie" to further twist the knife.
- Debut: "Blame It On Lisa"
A poor 8-year-old orphan Brazilian boy that Lisa supports.
- Conveniently an Orphan: Lampshaded. Ronaldo says he has the money to help the Simpsons because he doesn't have parents to take it from him, like so many child stars in America do.Ronaldo: I make as much as Malcolm in the Middle, and because I have no parents, my earnings remain un-stolen.
- Debut: "Blame It On Lisa"
- Affably Evil: Unlike César and Ugolin, they're actually quite friendly.
- Lima Syndrome: Develops this towards Homer, who has Stockholm Syndrome towards them, even compiling a scrapbook for his kidnapping.
- No Name Given: Their names are unknown.
Tina and Carrie
Two girls that Lisa meets while taking private gymnastic lessons with Lugash.
- Older Than They Look: They're college-aged, but look like 8-year-olds due to their small height.
- Debut: "Bart vs. Lisa vs. the Third Grade"
The third grade teacher at Springfield Elementary School.
- Foil: She displays a certain degree of cheerfulness, confidence and competence (at least until she witnesses a failure of the buddy system), as opposed to being downbeat or exasperated like Edna Krabappel and Elizabeth Hoover, both of whom McConnell dislikes.
- Living Prop: Being one of the teachers, she's made a few cameos.
- Sadist Teacher: Despite her upbeat demeanor, she penalizes students who tattle and moan (even if they're A-students), shows no sympathy towards those who cry, and initially pairs up students who clearly do not get along at all, causing even more friction in the class.
Frank Grimes, Jr.
- Debut: "The Great Louse Detective"
The illegitimate son of Frank Grimes and an enemy of Homer Simpson who wants revenge for his father's death.
- Revenge: He attempts to kill Homer because thinks that Homer "killed" his father by driving him insane.
- Strong Family Resemblance: He is identical to his father.
- Debut: "The Dad Who Knew Too Little"
A private detective hired by Homer to spy on Lisa and report his discoveries so Homer could appear to know facts about her life.
- Voiced by: Marisa TomeiDebut: "A Star Is Born-Again"
A movie star who falls in love with Ned Flanders.
- Alliterative Name: Sara Sloane.
- Expy: Of Notting Hill's Anna Scott.
- I Choose to Stay: Subverted. When Sarah asks Ned to join her in Hollywood and Ned declines, she chooses to stay in Springfield. But when Ned pressures Sara for marriage, they break up and she returns to Hollywood.
- Ms. Fanservice: She wears revealing fashion and acts in nearly topless roles for a romantic film. At a concert she wears a red Sexy Backless Outfit with Absolute Cleavage, gaining even more attention from men.
- Shout-Out: Sara's name is probably a pun on actress Sharon Stone, to whom she bears a slight resemblance.
- Single Woman Seeks Good Man: Sara Sloane is attracted to Ned's down-to-earth nature, and almost marries him.
- Voiced by: Jonathan Taylor ThomasDebut: "Dude, Where's My Ranch?"
Lisa's thirteen-year-old boyfriend at the Lazy I Ranch.
- Voiced by: Jane LeevesDebut: "The Regina Monologues"
A lady who Abraham Simpson encountered in England during World War II. They had a good relationship, but Abe unknowingly impregnated Edwina, and left England. Nine months later, Edwina gave birth to Abbie Simpson.
- Debut: "The Regina Monologues"
- Abandoned War Child: Abbey is the daughter of Edwina, a woman with whom Abraham Simpson briefly had a relationship while he was stationed in England during World War Two. Abbey is the result of that relationship.
- Distaff Counterpart / Uncanny Family Resemblance: She looks like Homer in drag, or the woman Bart mistakes for Homer in "Brother From The Same Planet".
- Voiced by: Sarah Michelle GellarDebut: "The Wandering Juvie"
Gina Vendetti is a young girl who is in a juvenile prison for girls. She and Bart escape from juvie after going to a dance.
- Broken Bird: She's got no family and has been stuck in juvenile hall for a LONG time.
- Heel Realization: Gina has one when she and Bart are arrested, and told that Bart will stay in juvenile hall even longer because of her. It inspires her to confess to Lou and Eddie that she was the one behind the escape.
- Jerk with a Heart of Gold: Gina is a vicious and cruel delinquent, and is not only willing to lie to get Bart in trouble, but threaten and attack him a few times. However, it turns out her anger is due to having no family, and when she learns what Bart will go through because of her, she confesses to forcing him to make a prison break.
- Knife Nut: When she's introduced.
- Manipulative Bitch: Gina claims she can act all sad to make Bart take the blame for their escape. After seeing her act, Bart claims he is screwed.
- Meaningful Name: Gina's surname of Vendetti is a clear pun on "vendetta", which is Italian for "revenge", referring to her vicious and manipulative nature.
- Tsundere: She kisses Bart, punches him again, hugs him, cries, and then punches him again. Bart is very confused by this girl.
- Voiced by: Kim CattrallDebut: "She Used to Be My Girl"
She is a famous, Peabody Award-winning reporter from the Global Television Network.
- Intrepid Reporter: Even reporting on top of an erupting volcano doesn't scare her.
- Self-Made Woman: Chloe went to high school with Marge and the two were best friends. They were both star reporters and had promising futures, however Marge decided to stay with Homer, while Chloe abandoned her sweet-heart (Barney Gumble) for success. She would later return to Springfield as a successful reporter.
- Debut: "Fat Man and Little Boy"
The owner of Goose's Gags and Gifts.
- Alliterative Name: Goose Gladwell.
- Beware the Silly Ones: Eccentric demeanor notwithstanding, Goose is more intelligent than he lets on.
- Captain Ersatz: Of Gene Wilder's portrayal of Willy Wonka in Willy Wonka & the Chocolate Factory.
- Older Than They Look: He looks like he's in his 30s, but says he went insane while serving in Vietnam, which would put him in his 50s.
- Shell-Shocked Veteran: Apparently, Gladwell was driven nuts in Vietnam.
- Debut: "Midnight Rx"
A Canadian counterpart for Ned Flanders.
- Evil Counterpart: Ultimately, Ned views him as such after he offers him a marijuana joint, saying "It's legal here".Ned: (glares at him) They warned me Satan would be attractive. Let's go!
- Identical Stranger: Looks just like Ned only with lighter brown hair.
- Palette Swap: Of Ned's normal outfit.
- Verbal Tic: He also says "diddly" and "doodley". He and Ned converse almost exclusively in "diddlys" and "doodleys", perplexing Homer and Apu.
- Voiced by: Lucy LiuDebut: "Goo Goo Gai Pan"
The adoption center worker who battles with Selma Bouvier when she tries to adopt her baby.
- Disappeared Dad: Madam Wu's dad died from choking on a ping pong ball one day before the Heimlich Maneuver was invented.
- Obstructive Bureaucrat: She acts like a Jerkass to Marge and the family, and takes Ling from Selma when she learns about how she is not married to Homer. However, she eventually relents as since her mom raised her alone, Selma herself can raise Ling.
- Voiced by: Amy PoehlerDebut: "Future-Drama"
Jenda (formerly Jenda Simpson) is Bart's future girlfriend and eventual ex-wife.
- Interspecies Romance: After being divorced from Bart, she gets a new partner called Jerry that is an Alien expy.
- Jerkass: In "Future-Drama", she gives Bart an ultimatum: staying and having sex with her or saving Lisa's future.
- The Load: She comes across as this a lot of the time as the futures where Bart ends up with her end up turning out far worse for him then the futures where he doesn't.
- Recurring Character: In the "Future" episode trilogy.
- Ugly Guy, Hot Wife: With Bart in "Days of Future Future". Though Bart is not really ugly, just slovenly.
- Voiced by: Ray RomanoDebut: "Don't Fear the Roofer"
A roofer who Homer ends up being friends with.
- Ink-Suit Actor: Ray Magini is voiced by Ray Romano and is designed to look like and talk like Ray Romano.
- Not-So-Imaginary Friend: Homer struggles to convince everybody of Ray's actual existence.
- Significant Anagram: "Ray Magini" is an anagram of "imaginary", as Lisa points out in the end.
Scammer and Z-Dawg
- Debut: "The Heartbroke Kid"
A hip-hop snack mascot duo.
- Cool Hat: Z-Dawg wears a red-and-white striped Cat in the Hat-style hat.
- The Man Is Sticking It to the Man: Lindsey Naegle describes them as "spokesrebels".Scammer: Yo, don't flava hate, participate!
- Vengeful Vending Machine: Bart destroys them and takes their money.Z-Dawg: Dude, you've changed!Scammer: Yo, I'm gonna cap a pop in yo ass!(starts shooting soda cans)
- Voiced by: Albert BrooksDebut: "The Heartbroke Kid"
The counselor of the fat camp, Serenity Ranch, Bart goes to after he getting fat from Scammer and Z-Dog snacks from the school vending machines.
- Bunny-Ears Lawyer: He has some serious mental issues, but is an effective weight-loss coach.
- Drill Sergeant Nasty: He's a retired US Marine turned weight loss coach, making him both variants. One exercise he has patients perform is pulling him on a chariot while he whips them.
- Jerk with a Heart of Gold: An abrasive coach, but he cares about Bart's personal well-being.
Coach Clay Roberts
- Debut: "Home Away from Homer"
A wrestling coach who moves next door to the Simpsons after Ned sells his house to him.
- Jerkass: He quickly asserts himself and treats Homer very poorly.
- Jerk Jock: He is a wrestling coach. He moves away at the end of the episode after Ned overpowers him.
- Voiced by: Liam NeesonDebut: "The Father, the Son and the Holy Guest Star"
- Voiced by: Lily TomlinDebut: "The Last of the Red Hat Mamas"
The leader of the Cheery Red Tomatoes, a women's society.
- Jerkass: She creates the heist to steal Fabergé eggs from Montgomery Burns and recruits Marge for her thinness, as she can fit through pipes to open the door. However, when they fail, but Marge has one Fabergé egg hidden in her hair, she takes it and tells Marge that for 'safety' they should never meet again, indicating that their 'friendship' was nothing.
- Voiced by: Maria Grazia Cucinotta, Tress MacNeille in "Funeral for a Fiend"Debut: "The Italian Bob"
She is Sideshow Bob's wife and is Italian. They have a son named Gino.
- Chuck Cunningham Syndrome: She and her son disappear after their second appearance in "Funeral for a Fiend" with no mention of where they went (for the record, Bob has appeared several times since).
- Dark Chick: She became this in the Bob family.
- FaceHeel Turn: At first she knew nothing of her husband's multiple murder attempts. When she does become aware, she helps Bob try to kill the Simpsons family.
- Happily Married: With Bob.
- Impossibly-Low Neckline: She has an off-the-shoulder top with a considerable amount of cleavage showing.
- Ink-Suit Actor: Her design may be based on her voice actress Maria Grazia Cucinotta.
- Debut: "The Italian Bob"
- Ax-Crazy: Like father, like son.
- Bad People Abuse Animals: His first episode ends with him trying to kill butterflies.
- Chuck Cunningham Syndrome: He and his mother disappear after their second appearance in "Funeral for a Fiend" with no mention of where they went (for the record, Bob has appeared several times since).
- Enfant Terrible: He may be cute but he's quite deadly.
- Hereditary Hairstyle: His hair looks similar to Sideshow Bob's hair (resembling a palm tree).
- Voiced by: Michael YorkDebut: "Homer's Paternity Coot"
A treasure hunter. He is 66 years old.
- Luke, I Am Your Father: Subverted. Homer tracks him down after he discovers old love letters written by Fairbanks to his mother, Mona, and begins to believe he may be his biological father. The paternity test reveals Fairbanks to be Homer's father, but at the end of the episode, Abraham admits to having switched the DNA samples, wanting to preserve the happiness Homer had been feeling with Fairbanks.
- Voiced by: Ricky GervaisDebut: "Homer Simpson, This Is Your Wife"
A man who temporarily becomes Marge's husband on the reality TV show Mother Flippers. He is 37 years old.
- Because You Were Nice to Me: Charles soon falls in love with Marge as she's much kinder than his real wife Verity.
- Voiced by: Ricky GervaisDebut: "Homer Simpson, This Is Your Wife"
- Bi the Way: On the final day of the show, she reveals that she is getting a divorce from Charles and is going out with Patty, which implies she is bisexual.
- Domestic Abuse: She went onto Mother Flippers to disgrace and punish her husband. She criticizes everything Charles and her son, Ben, does.
- Voiced by: Frances McDormandDebut: "Girls Just Want to Have Sums"
The temporary principal of Springfield Elementary. She split the school into two groups: boys and girls.
- Straw Feminist: Melanie is a sexist woman, favouring the girls and not caring in the slightest about the boys. She lets the boys' side of the school get dirty and look like a gang scene in a ghetto neighborhood, with broken equipment. She also has a cage door put in the back of the bus for boys to travel like criminals, while the girls ride normally.
- Voiced by: Mandy MooreDebut: "Marge And Homer Turn A Couple Play"
Tabitha is the wife of Buck Mitchell and also a pop singer and celebrity in Springfield.
- Dude Magnet: It appears Tabitha can attract males of any age, as Bart seems to show slight attraction when she uses the lamp as a pole-dancing pole.
- Hello, Nurse!: The reaction at every show of Tabitha. Running Gag with Bart.
- Lust Object: Lampshaded several times in the episode.Homer: "Buck, you've got a beautiful woman with a hot body that any man would fantasize about even while making love to his own Marge".
- Ms. Fanservice: So much so that in her show a sign warns "first ten rows may get horny".
- Shameless Fanservice Girl: The source of her marriage problem. Tabitha apparently likes showing off her body in public during her performance, which gets her husband Buck really angry.
- Debut: "Marge And Homer Turn A Couple Play"
Buck is the husband of Tabitha Vixx and also a baseball player for the Springfield Isotopes and a well-known celebrity in Springfield.
- Debut: "The Mook, the Chef, the Wife and Her Homer
Fat Tony's son.
- Creepy Child: Is the son of a mob boss who poisons a rival family when they shoot his dad.
- Early-Bird Cameo: Fat Tony was said to have a son called Michael back in Season 16.
- Expy: Of Michael Corleone from The Godfather.
- I Am Not My Father: Starts off playing this straight then subverts it.
- I Just Want to Be Normal: He does not wish to follow in his father's footsteps and go into the family business of "waste management".
- Overlord Jr.: Is set to become the head of the Springfield Mafia when he grows up.
- Supreme Chef: He has a passion for cooking and is a great chef. His food is said to be really good even though he's afraid to tell his father.
- I Surrender, Suckers: Invites a rival mob family to dinner to make peace with them then poisons them.
- Shrinking Violet: Very awkward around people, made even worse when he becomes The Dreaded.
- Voiced by: Natalie PortmanDebut: "Little Big Girl"
A girl from North Haverbrook. Bart gets a crush on her.
- Teen Pregnancy: Bart dates her, but shortly Darcy reveals that she is one of these. The father is apparently a Norwegian exchange student, who went back to "Norwegia".
Dr. Stacey Swanson
- Voiced by: Meg RyanDebut: "Little Big Girl"
A psychiatrist, whom Principal Skinner makes Bart go see for five sessions.
- Dramatic Irony: Bart is sent to therapy for scaring children with tales of "Dark Stanley", a Lethal Chef who cannibalizes kids. When Dr. Swanson sees her own psychiatrist, it is revealed during their session that "Dark Stanley" is in fact real and killed her own son.
- The Shrink: Of the awesome type. Bart develops a close bond with her and when his sessions end, he starts to miss the time he spent with her and enters into a state of depression in which he talks about his problems to an empty chair while lying on his bed. Marge, worried, pays for one more session with Dr. Swanson. When it ends, Bart feels that he has been able to get everything off his chest.
- Debut: "The Boys of Bummer"
A retired baseball player who dropped an easy catch a long time ago.
- Butt-Monkey: People still seem to remember his fail, like Grampa who hates him for it.
- Hypocrite: He's very evil towards Bart after learning his name, despite also failing to catch a ball in his younger years. Lisa calls him out on this.
- Jerkass: At first, he is shown to be an honest role model for Bart, who became the town's black sheep for failing to catch a baseball. But once he learns Bart's name, he bullies the kid to the point of tears, which eventually contributes to his attempted suicide.
- Pet the Dog: When Bart attempts suicide by jumping off the water tower and everyone worries for him, La Boot tries to catch him, only to miss.
- Debut: "Homerazzi"
The Rich Texan's daughter.
- Voiced by: Albert Brooks
The power-mad head of the EPA, he decides to take drastic action against Springfield when the town's pollution reaches a critical level.
- Bad Boss: After the Simpsons manage to escape the dome, he angrily throws his binoculars at a nearby aide, who dodges them. Karma immediately bites him in the ass as they bounce back from the dome and into his eyes.
- Big Bad: Of the movie.
- Convenient Replacement Character: For Hank Scorpio of "You Only Move Twice". Word of God considered bringing back Scorpio, however they thought Scorpio was too likeable to turn into an all-out villain. They not only share the same voice actor, they have the same voice, too.
- Corrupt Corporate Executive: His company constructed the dome that seals off Springfield.
- Drunk with Power: As he himself lampshades, as going mad without power is boring.
- Knight Templar: Initially he just seals Springfield under a dome, but then he decides to level it and its inhabitants.
- Well-Intentioned Extremist: Initially. While he wants to stop pollution at all costs, nuking Springfield and its people and going out of his way to make sure no one escapes (and trying to force back the few people who do manage to escape) is overkill.
Medicine Woman (Boob Lady)
An Inuit woman who briefly takes Homer in when he gets lost in Alaska. She nurses him back to health and makes him have an important epiphany about his family and Springfield.
- The Cameo: Appears in the opening sequence directly following the movie and makes a brief speaking cameo in "Boy Meets Curl", wherein Homer refers to her as his therapist and the two have a... "session" together.
- Gainaxing: The reason Homer dubs her "Boob Lady".
- Magical Native American: An Inuit version.
- No Name Given: Despite her rather notable role in the movie, her name never gets mentioned.
- Never Heard That One Before: Being Irish and an environmentalist, he isn't surprised when Lisa asks if Bono is his dad.
- Voiced by: Stephen ColbertDebut: "He Loves to Fly and He D'ohs"
The life coach Marge hires to help Homer get a more successful job.
- Voiced by: Maya RudolphDebut: "The Homer of Seville"
Homer's manager after he becomes a famous opera singer.
- Biker Babe: Her first appearance is on a motorcycle, saving Homer and Marge from an mob of fans.
- Bitch in Sheep's Clothing: At first, Julia appears to be a polite and friendly woman, but upon developing her obsession with Homer, she becomes ready to do anything to get his attention without Marge's awareness, then blames Homer for having harassed her.
- Ms. Fanservice / Shameless Fanservice Girl: When Julia reveals her true intentions to Homer, she strips naked and tells him that he can have her anytime he wants. Over the next few days, she keeps appearing in sexually suggestive positions.
- Revenge: While she is being sent to an insane asylum, she swears to get Marge for stopping her from trying to kill Homer.
- Stalker with a Crush: To Homer when he becomes an enormous celebrity in the opera.
- Yandere: She tries to seduce Homer multiple times, but he refuses. Not accepting refusal, she tries to kill him.
- Voiced by: Matt DillonDebut: "Midnight Towboy"
A tow truck driver.
- Voiced by: Steve BuscemiDebut: "I Don't Wanna Know Why The Caged Bird Sings"
A criminal who robbed a bank.
- Butt-Monkey: He was abandoned by his mother when he was a boy, he has three dye packs blow up in his face during the robbery, Marge is too nervous to visit him in prison, he escapes prison through a sewer pipe instead of the one dispensing spring water next to him, and he throws himself into the gears of the Viking ship ride to save Chief Wiggum.
- Heroic Sacrifice: Subverted. Dwight is willing to attempt one when he throws himself into the gears of the Viking ship ride at the amusement park to save Chief Wiggum. However, he somehow survives this and makes a full recovery, after having to be hospitalized.
- Parental Neglect: Dwight's mother took him to an amusement park as a child and abandoned him there. He kidnaps Marge and takes her there so he can relive the time he lost.
- Stupid Crooks: Implied. Dwight undergoes the bank robbery without gloves, a mask, or covering himself up, meaning that his DNA would be present at the crime scene and CCTV would capture him, though it probably wouldn't have made much difference due to how the Police are Useless in Springfield.
Dr. Robert Terwilliger, Sr.
- Voiced by: John MahoneyDebut: "Funeral for a Fiend"
Father of Sideshow Bob and Cecil.
- Longer-Than-Life Sentence: 87 years behind bars with his family, signaling that he'll die in prison.
Dame Judith Terwilliger (née Underdunk)
- Debut: "Funeral for a Fiend"
Mother of Sideshow Bob and Cecil, and a retired Shakespearean actress.
- Drama Queen: She acts like one, just moments after her husband's "fake death" IV has fully taken effect on their son's body. Justified, since she is a Shakespearean actress herself.
- Hereditary Hairstyle: Her sons get their extremely curly hair from her.
- Longer-Than-Life Sentence: 87 years in prison with her family, meaning she'll die before she's out.
- Strong Family Resemblance: She looks like an elderly female version of Sideshow Bob.
- Debut: "That '90s Show"
A professor at Springfield University and a love interest of a younger Marge.
- Jerkass: All in all, he's a condescending and misogynistic asshole.
- Manipulative Bastard: He broke Homer and Marge up so he could have her for himself.
- Small Name, Big Ego: He acts like the ultimate authority on feminism and what women should want to do and be in life, but he's really not.
- Teacher/Student Romance: Marge fall in love with him and eventually started to imagine Homer as him. Marge left Homer for Stefane and they started dating until Marge found out he didn't want to get married at all and that he was actually not at all like her.
- Voiced by: Topher GraceDebut: "The Debarted"
An orphan from Shelbyville and a student at Springfield Elementary School.
- Always Someone Better: Initially to Bart being a better prankster. However, it was just an act.
- Becoming the Mask: Donny and Bart become best friends, although Donny decides to leave Springfield.
- The Mole: He originally worked for Skinner and Chalmers. His goal was to enter Bart's circle of friends to snitch on Bart's plans.
- Voiced by: Karl WiedergottDebut: "Papa Don't Leech"
The long-lost father of Lurleen Lumpkin.
- Hoist by His Own Petard: When the Dixie Chicks learn of the theft, they join with Lurleen in beating up Royce with their instruments.
- Jerkass: He not only re-abandons Lurleen, but also steals her new song "My Daddy's Back", rewrites the lyrics and gives it to the Dixie Chicks as "America's Back", telling them that he wrote the song. This backfires as described above.
- Parental Neglect: To Lurleen. Royce abandoned her when she was four years old. He doesn't reappear in her life until thirty years later, when Marge Simpson tracks him down. They have a joyous father-daughter reunion, which inspires Lurleen to write a song called "My Daddy's Back". All too soon, however, Royce reverts to type and abandons Lurleen again.
- Voiced by: Nancy CartwrightDebut: "Double, Double, Boy in Trouble"
A rich boy who looks exactly like Bart.
- Identical Stranger: He looks exactly like Bart (who describes Simon as a "nerd version of himself")
- Prince and Pauper: Bart swaps places with Simon... whose siblings are trying to kill him.
- Wouldn't Hit a Girl: When Lisa, who suspects that he is not Bart, hits him, she tells him Bart would have hit her back in retaliation.
- Debut: "Dangerous Curves"
A European who met Marge five years ago when she and Homer was out on a road trip with Patty and Selma.
- Camp Straight: He acts very flamboyant but is apparently straight.
- Debut: "Dangerous Curves"
A woman who met Homer five years ago when he and Marge was out on a road trip with Patty and Selma.
- Voiced by: Emily BluntDebut: "Lisa the Drama Queen"
A girl who Lisa befriends.
- Cloudcuckoolander: She likes roleplaying and has an overactive imagination, preferring to live in her fantasy world rather than the real one.
- Romantic Two-Girl Friendship: With Lisa. In their fantasy world, they're the two queens who rule over the land of Equalia. And then they run away together when Marge, fearing that their friendship is having a bad effect on Lisa, attempts to separate them. Adding to that, their episode is based on the plot of Heavenly Creatures, in which the girls ARE budding baby lesbians.
- Debut: "Bart Gets a "Z""
The teacher that briefly replaces Edna Krabappel as the fourth grade teacher at Springfield Elementary School.
- The Alcoholic: He is fired after he puts vodka in his energy drink and insults the students while drunk. Ironically, Bart considers doing the exact same thing to him in an attempt to get Krabappel back before deciding instead to admit he was responsible for Krabappel's firing.
- Cool Teacher: He is thought to be cool by most of the kids, using Facebook, Twitter, and sending text messages to the kids instead of giving them actual work.
Charlie (O Brother, Where Bart Thou)
- Voiced by: Jordan NagaiDebut: "O Brother, Where Bart Thou?"
A boy who is briefly "adopted" by Bart.
- Outnumbered Sibling: At the end, he is adopted by a couple with six daughters.
- Siblings Wanted: Charlie is this to Bart. In the episode Bart decides he wants a brother after seeing the bond between his sisters, Lisa and Maggie. But Marge explains that even if she and Homer did end up having another baby, the baby could end up being another girl instead of a boy. After realizing that, he decides to try and adopt a kid from the orphanage where meets Charlie who sneaks out. The two of them have fun by doing various activities until he is legally adopted by a real family.
- Voiced by: Jonah HillDebut: "Pranks and Greens"
A former student of the Springfield Elementary School.
- Basement-Dweller: In present, Bart and Milhouse meet Andy and learn that he is unemployed and lives with his mother. Bart helps him get a job.
- Mundane Utility: Thanks to his pranking abilities, he is hired as Krusty's writer for his TV show.
- The Prankster: He is said to be the best prankster ever. His first and most famous prank was when Andy was a student at Springfield Elementary School and Seymour Skinner loved to swim in the school's early swimming pool. Andy filled the pool with worms and locked Skinner in the pool for a whole weekend, including Monday, a teacher's holiday.
Penelope Owsley (aka Princess Penelope)
- Voiced by: Anne HathawayDebut: "Once Upon a Time in Springfield"
A new addition on "The Krusty the Clown Show", originally put in to attract more female viewers.
- All of the Other Reindeer: Penelope explains her love for Krusty is because she felt he was the only friend she had when she was 12, since she wasn't popular for being more pretty and friendly than the other girls who in return isolated her.
- All There in the Manual: According to The Simpsons: Tapped Out game, Penelope left Krusty. In the game she is again used to diversify Krusty's demograph, but this time for his theme park Krustyland.
- Ascended Fangirl: She is shown to have been a lifelong fan of Krusty and the two then have a romantic relationship.
- Everything Is Better With Princesses: Princess Penelope is added in The Krusty Show specifically to exploit this trope.
- Fangirl: Of Krusty.
- Overly Long Name: Her actual name is Penelope Mountbatten Hapsburg Hohenzollern Mulan-Pocahontas.
- Princesses Prefer Pink: Penelope wears a beautiful pink dress (similar to that of Disney princesses).
- What Happened to the Mouse?: In the show, it is not revealed how her relationship with Krusty ended up.
- Voiced by: Sarah SilvermanDebut: "Stealing First Base"
- Distaff Counterpart: To Bart, in terms of skateboarding. And, like Bart, she seems to be a rebel, but apparently with a better reputation.
- Tsundere: She's definitely Harsh type. She goes from being upset because Bart stole a kiss from her, to wanting to be his girlfriend. He still can't figure her out by the end of the episode (though Bart did cry out, "I love you!" to her as she left).
- Voiced by: Sasha Baron CohenDebut: "The Greatest Story Ever D'ohed"
Jakob is an Israeli tour guide in charge of the Simpson family's tour to Israel.
- Egocentrically Religious: He is pretty condescending and disrespectful towards other religions.
- Voiced by: Yael NaimDebut: "The Greatest Story Ever D'ohed"
- Action Girl: She is a highly skilled practitioner of the Israeli martial art of Krav Maga. When Bart runs away from the tour group, she uses it to great effect to pursue and subdue him.
- Badass Israeli: Dorit pretty much can take care of herself.
- Groin Attack: To Bart.
- Debut: "The Bob Next Door"
Ted Flanders is a member of the Flanders family who moved next door to the Simpsons after Sideshow Bob (disguised as Walt Warren) was sent to jail.
- Voiced by: Kristen WiigDebut: "Flaming Moe"
The substitute music teacher for the music class at Springfield Elementary School after Mr. Largo quits.
- Hippie Teacher: "You can't teach music. You embrace music. Oh, you inhale music. You roll around in a pile of music until... the scent of music is on you, forever."
- Multicolored Hair: She has red hair with purple and pink streaks.
- Romantic False Lead: To Skinner. He dated her for three months.
- Voiced by: Alyson HanniganDebut: "Flaming Moe"
A 3rd grader at Springfield Elementary School and the daughter of Ms. Juniper.
- Dogged Nice Girl: Bart wasn't interested in dating her.
- Fangirl: Melody happens to be a big fan of Bart, as she keeps a dream journal containing many drawings of him and her.
- Girlish Pigtails: Her hairstyle.
- Meganekko: An adorkable girl with glasses.
Crazy Dog Man
- Debut: "The Blue and the Gray"
A man who owns many dogs. He seems to temporarily be a love interest of the Crazy Cat Lady.
- Spear Counterpart: To the Crazy Cat Lady.
- The Unintelligible: Like the Crazy Cat Lady, he speaks in incomprehensible wails and grunts. Somehow, they manage to converse with one another.
The Great Raymondo
- Voiced by: Martin LandauDebut: "The Great Simpsina"
A retired magician who accepts Lisa as his apprentice.
- The Lost Lenore: His wife and former assistant Esther. It is unclear how she died, but at the end of the episode, Raymondo drugs himself and hallucinates Esther standing before him, dancing with her until the fade to black.
- Retired Badass: Despite his age he defeats his young magician rivals.
- Stage Magician: His old work. He claims to be a famous illusionist for his greatest and most famous trick, The Great Milk Can Escape.
- Voiced by: Jack McBrayerDebut: "The Great Simpsina"
A young hillbilly and folk musician.
- Offscreen Teleportation: He starts singing The Peach Song, a very long song about peaches, to Bart and Lisa. As they try to run away from him, he keeps appearing in different places, still singing and annoying Lisa and Bart.
- Voiced by: Kristen SchaalDebut: "Homer Scissorhands"
A fifth-grader who briefly fell in love with Milhouse.
- Give Geeks a Chance: To Milhouse. During lunch, Taffy overhears Milhouse proclaim his love for Lisa, only to be rebuffed by her. Impressed by Milhouse's action, she falls in love with him and begins dating him.
- Insane Troll Logic: She dumps Milhouse when they spot Lisa, who followed them to Reaching Hands Point, because she thinks Milhouse might still love Lisa.... despite the fact that he didn't do anything.
- Voiced by: Kiefer SutherlandDebut: "The Falcon and the D'ohman"
A former CIA agent who is employed as a guard at the Springfield Nuclear Power Plant, where he meets Homer.
- Voiced by: Joan Rivers.Debut: "The Ten-Per-Cent Solution"
A veteran agent and a helper of Krusty the Clown.
Springfield Nuclear Power Plant Robots
- Voiced by: Brent SpinerDebut: "Them, Robot"
- Three-Laws Compliant: Their primary objective is to protect humans, even stopping Homer from having beer.
- Voiced by: Aniki Noni RoseDebut: "Gone Abie Gone"
A former restaurant singer who is in a relationship with Abraham Simpson, whom she married.
- Chuck Cunningham Syndrome: Despite Rita and Abe reconciling at the end of her episode and continuing to develop their relationship, she's never seen or mentioned again.
- Remember the New Guy?: She was Abe's second wife and the stepmother of Homer. Abe and Homer never mention Rita before the episode "Gone Abie Gone".
- Handy Feet: She can play the piano with her toes.
- Verbal Tic: Rita has a habit of ending her sentences with "yeah".
- Voiced by: Tina FeyDebut: "Black-Eyed, Please"
The substitute teacher at Lisa's class.
- Asshole Victim: She suffers from Bart's antics as a result of her being heartless to his sister, causing a major Villainous Breakdown that ends with her fleeing Springfield. Given what had happened to other women who forced to babysit him before, it is plausible she's snapped completely.
- Jerkass: She pratically bullies Lisa for awful reasons.
- Kick the Dog: There's not a moment where she doesn't attack Lisa out of hatred, not even in her final scene.
- Sadist Teacher: To Lisa. She punishes her harshly for any reason, takes every chance to belittle and mock her, and gives her poor grades despite good work.
- Voiced by: Kristen Wiig
- Posthumous Character: Chip Davis is never seen throughout the series. His only (mentioned) appearance is at his funeral when the people of Springfield reminisce on how he made an impact on their lives.
- Debut: "Four Regrettings and a Funeral"
Mr. Burns' cousin and lover.
- Bald Woman: Her black hair is actually a wig.
- Kissing Cousins: She has no problem hooking up with her cousin Mr. Burns neither in the past nor present.
- Older Than They Look: Even taking the baldness into account, she doesn't look nearly as old as her cousin.
- Voiced by: Elisabeth Moss
- Voiced by: Eva Longoria
Deputy Director Gratman
- Voiced by: Will Arnett
- Voiced by: Kristen Bell
- Bitch in Sheep's Clothing: She's initially nice to Lisa, but begins to treat her like dirt after their fathers become friends. Her trying to replace Lisa's bicycle is the last straw.
- It's All About Me: Harper is very pushy, and tries to take control of Lisa's life.
- Spoiled Brat: Her father is extremely rich, which turned Harper into a selfish and spoiled kid.
- Dating What Daddy Hates: Inverted. He's friends with the Simpsons (especially Homer), but is forced to break it off when they realize that Harper and Lisa hate each other.
- Rich Bastard: Subverted. He and Homer discover that they also have a lot of things in common and become friends until Harper and Lisa's last fight, with being Homer forced to make a hard decision: go home, so Lisa can be more happy.
- Screw the Rules, I Have Money!: He invites the Simpsons family to spend a week at their private island, but they can't go as the kids have school. That's when Skinner calls the Simpsons, saying that school next week has been cancelled (thanks to Mike's money).
General Clancy Wiggins
- Voiced by: Sarah Silverman
- Chekhov's Gunman: She may be the same imaginary Rachel as Lisa's imaginary friend in "Today, I Am A Clown".
- Yandere: She murders Lisa's friends so that she'll be Lisa's only friend.