Characters / The Simpsons One Time Characters Seasons 21 To 30

Season 21

Zachary Vaughn

Voiced by: Hank Azaria

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. Even when he gets himself wasted at school, he vouches for Bart when Skinner is quick to accuse him, when he could have easily continued his drunken rant.

Andy Hamilton

Voiced by: Jonah Hill

Debut: "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.

Charlie (O Brother, Where Bart Thou)

Voiced by: Jordan Nagai

Debut: "O Brother, Where Bart Thou?"

A boy who is briefly "adopted" by Bart.

• 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.

Penelope Owsley (aka Princess Penelope)

Voiced by: Anne Hathaway

Debut: "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.
• Fangirl: Of Krusty.
• Gratuitous Princess: Princess Penelope is added in The Krusty Show specifically to exploit this trope.
• 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).
• Shown Their Work: Her full name contains 3 different European royal names. Mountbatten is the last name of Queen Elizabeth II's husband, Phillip Mountbatten, Duke of Edinburgh, though his descendants have no last name to keep it the House of Windsor. The house of Hapsburg, also spelled Habsburg, were the rulers of Spain and Austria-Hungary up until 1918. The house of Hohenzollern is the name of the rulers of Germany until 1918, also.
• What Happened to the Mouse?: In the show, it is not revealed how her relationship with Krusty ended up.

Eliza Van Houten (née Simpson)

Voiced by: Yeardley Smith

Debut: "The Color Yellow"

Virgil Simpson

Voiced by: Wren T. Brown

Debut: "The Color Yellow"

Mabeline "Mabel" Simpson

Voiced by: Julie Kavner

Debut: "The Color Yellow"

Hiram Simpson

Voiced by: Dan Castellaneta

Debut: "The Color Yellow"

Colonel Wainwright Montgomery Burns

Voiced by: Harry Shearer

Debut: "The Color Yellow"

Nikki McKenna

Voiced by: Sarah Silverman

Debut: "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 the Harsh type. She goes from being upset because Bart stole a kiss from her, to wanting to be his girlfriend, to back to hating him, to back to loving him. She seems to act opposite of whatever Bart feels for her; if Bart acts affectionate, she will utterly despise him and refuse to be his girlfriend, but if Bart acts dismissive and angry and tries to leave her, she will instantly be attracted to him. And when Bart fell of the school roof and was seemingly dead, she cries that she loved him, but when he saw he was alive he called him a loser. 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).
  • Her later cameo in "Moonshine River" has her go from stating Bart has a lot of nerve coming back to her, to demanding a kiss from Bart, recoiling and calling it inappropriate, saying she missed him, calling him a stalker, and then calling out to a fleeing Bart to "save [her]".

Jakob

Voiced by: Sacha Baron Cohen

Debut: "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.

Dorit

Voiced by: Yael Naim

Debut: "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.

Burns' Inmate

Ted Flanders

Voiced by: Dan Castellaneta

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.

• Distaff Counterpart: His daughters Bonnie and Connie to Rod and Todd.
• Strong Family Resemblance: He is very similar to Ned. He also speaks just like Ned and looks like him, too. Much to Homer's chagrin.

Season 22

Calliope Juniper

Voiced by: Kristen Wiig

Debut: "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."
• Romantic False Lead: To Skinner. He dated her for three months.

Melody Juniper

Voiced by: Alyson Hannigan

Debut: "Flaming Moe"

A 3rd grader at Springfield Elementary School and the daughter of Ms. Juniper.

• Bespectacled Cutie: An adorkable girl with glasses.
• 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.

Crazy Dog Man

Voiced by: Dan Castellaneta

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 Landau

Debut: "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.

Ewell Freestone

Voiced by: Jack McBrayer

Debut: "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.

Taffy

Voiced by: Kristen Schaal

Debut: "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.

Season 23

Wayne Slater

Voiced by: Kiefer Sutherland

Debut: "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.

• But Now I Must Go: At the end of his debut episode, Wayne decides to leave Springfield claiming to the Simpsons that he can't stay in one place because Homer was kidnapped by Ukrainian mobsters who were after him. However Marge takes pity on him and helps him to get a job in the Springfield DMV with her sisters Patty and Selma.

• Dark and Troubled Past: Due to his years as a CIA agent, Wayne had multiple traumatic experiences from past missions (which one of them was him being imprisoned in North Korea and forced to write a play there about its leader) which left him distant from others, and also with PTSD (Post Traumatic Stress Disorder), which caused him to unknowingly attack Mr. Burns and thus getting himself fired.

• Foil: To Frank Grimes, while both of them were employees from the Springfield Nuclear Power Plant who faced hardships on their lives which hardened them and also disliked Homer when he wanted to befriend them. Wayne eventually warms up to Homer and accepts him as a friend, while Grimes died hating and trying to humiliate Homer.

• Friend to All Children: While serious around everyone else, Wayne is polite to the Simpson kids and even teaches them self-defense techniques, which comes handy to Bart against his bullies, also he teaches Maggie to communicate with rattle code.

• Jerk with a Heart of Gold: As a result of his past traumas, Wayne is usually distant and aloof towards everyone, but he saved Homer, Lenny, Carl and Moe from being robbed by Snake Jailbird, is polite towards the Simpson family and also rescued Homer when he was kidnapped by Ukrainian mobsters, which are old enemies of his, and even gives Homer the fist bump he refused to give him when they first met.

• Perpetual Frowner: Due to his serious personality, Wayne rarely smiles, only doing it at the end of his debut episode when giving Homer the first bump he wanted.

Annie Dubinsky

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 Spiner

Debut: "Them, Robot"

• Three Laws-Compliant: Their primary objective is to protect humans, even stopping Homer from having beer.

Season 24

Rita LaFleur

Voiced by: Anika Noni Rose

Debut: "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".

Ms. Cantwell

Voiced by: Tina Fey

Debut: "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 were forced to babysit him before, it is plausible she's snapped completely.
• Evil Counterpart: To Lisa's substitute teacher Mr. Bergstrom from way back in Season 2. Bergstrom was a dedicated, loving and excellent teacher who really did care for all of his students, and who became a giant inspiration for Lisa. Cantwell's traits are the opposite of these, and instead of inspiring Lisa she ceaselessly torments her.
• Fatal Flaw: Her pettiness and shallow-judgementalism. She tends to assume incorrect things based on people's appearances (assuming Lisa to be a party girl for her blonde hair and wearing pearls; thinking Skinner and Chalmers are a gay couple), which, in Lisa's case, results in her being petty and cruel to her, which in turn results in her torment at Bart's hands. While her pettiness means she will rather quit and be jobless than stop being mean to Lisa.
• Freudian Excuse: It can be assumed that she was a "bookworm" in her school years and was frequently outshined by "party girls." So now she is a Womanchild who acts like a petty and cruel bully to other girls who fit this definition in her eyes, including the eight-year-old nerd Lisa Simpson.
• Jerkass: She bullies Lisa for awful and petty reasons.
• Jerkass to One: Lisa is the only one she treats with disdain. She is pretty much a Cool Teacher to the other students at Lisa's class.
• 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.
• Womanchild: She bullied an eight-year-old girl because of an old wound from her school years and at one point is even seen sitting on a toilet by herself muttering "stupid Lisa" to herself like a bratty child mad at someone.

Season 25

Annie Crawford

Voiced by: Kristen Wiig

• Captain Ersatz / Expy: Of Homeland protagonist Carrie Mathison.

Chip Davis

• 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.

Lyla

Voiced by: Tress MacNeille

Debut: "Four Regrettings and a Funeral"

Mr. Burns' cousin and lover.

• 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.

Gretchen

Voiced by: Elisabeth Moss

Homer Jr.

Chase

The Atomettes

Isabel Gutierrez

Voiced by: Eva Longoria

Deputy Director Gratman

Voiced by: Will Arnett

Kumiko's father

Voiced by: Hank Azaria

Season 26

Princess Kemi

Voiced by: Yaya DaCosta

• Cute Bookworm: She is beautiful and loves reading.
• Girl in the Tower: While her father was busy negotiating with Mr. Burns an uranium deal she is forced to stay at a fancy hotel with Homer babysitting her.
• Graceful Ladies Like Purple: She is classy and wears a purple dress.
• Rebellious Princess: She gets Homer to give her a tour around the city despite her father's orders to stay in the hotel then ditches Homer when he is distracted to explore the city with Moe.
• Spoiled Sweet: She is very kind and well-mannered. She was very nice to Moe and never showed any disgust by his appearance.
• Unwitting Pawn: After Moe gets scammed by someone who claimed to be a Nigerian Prince he tries to get information from Kemi about whatever she has any brothers and she answers that she indeed has one. At first Moe wanted to get revenge against her brother since he truly believed that the con artist was a Nigerian Prince by using her to get to him but he ultimately abandons the idea upon seeing how pretty and nice Kemi was to him.

Harper Jambowski

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.
• Rich Bitch: She is VERY rich but is very rude to Lisa and constantly bosses her around while bribing her with expensive gifts so that Lisa won't leave her until Lisa grows tired of her behavior and breaks up their friendship.
• Spoiled Brat: Her father is extremely rich, which turned Harper into a selfish and spoiled kid.

Mike Jambowski

Voiced by: Hank Azaria

• 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 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: Dan Castellaneta

Season 27

Quinn

• Does Not Like Men: She belittles the boys in her computer class while praising Lisa as the only girl.
• Sadist Teacher: A cool teacher to Lisa but definitely this to her male students. She frequently talks down on them and later forces them to do mandatory physical exercise while she and Lisa work on their project.
• Straw Feminist: See above, she thinks that to be a woman in the computer programming industry she has to be twice as mean. She keeps her group of programers mostly girls while only hiring Comic Book Guy for "token equality" while keeping him separated from the rest of the group and takes everything he says as insulting.

Season 28

Season 29

Season 30

Anastasia Alekova

Voiced by: Ksenia Solo

Debut: "From Russia Without Love"

A con artist from the dark who almost married Moe.

• Alliterative Name: Anastasia Alekova.
• Con Artist: She pretended to be Russian while seducing Moe and later pretended to be Scottish when flirting with Willie.
• Gold Digger: Anastasia's goal is to marry a rich man, that's what she believed Moe to be and almost married him and left him when she saw that all he had to offer her was a lot of debts, so she flirted with Willie when she believed him to be rich, also she dated Krusty the Klown, a celebrity.
• Lack of Empathy: When Moe reveals his previous heartbreaks to her, Anastasia feigns sympathy, but then insults him in russian calling him "Nightmare Face".
• Mail-Order Bride: She was a mail-order bride ordered by Bart, Milhouse and Nelson as a prank to Moe.

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