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Portrayed by: Debby Ryan
- Action Girl: Probably the most capable fighter in the series. Justified since her military dad taught her.
- Adorkable: She can be clumsy or even silly at times, but is still a likable Nice Girl.
- Birds of a Feather: A platonic version of this with Officer Petey.
- Blonde, Brunette, Redhead: The redhead to Emma's blonde & Zuri's brunette.
- Book Dumb: Depending on the episode. Jessie just graduated high school before the pilot, but doesn't know the answer to a simple fraction problem that Luke had to do. In another episode, she also didn't know if a fraction with a denominator of zero would be undefined.
- Bunny-Ears Lawyer: Jessie is arguably the goofiest of them all, but is crazy-skilled, including singing, stripping a gun, survival training, hand-to-hand combat skills and being able to fly aircraft. It was also revealed in the pilot that she's a straight-A student. It's implied her dad is just as ditzy and skilled.
- Subverted since her military skills don't help her with her job as a nanny and the fact that her goofiness is a reason why she's arguably not the most competent nanny. Even although the kids love her, because she's like a Cool Big Sis to them, most of the time they don't show it they treat her like crap, step over her and don't pay respect to her and she can't help it.
- Butt-Monkey: She finds herself in this role more often than any character besides Bertram, but it's usually Played for Laughs.
- Cain and Abel: Abel to her stepsister Darla's Cain. Darla is shown to be disrespectful and Jessie doesn't like her at all.
- Cluster F-Bomb: Especially in G.I. Jessie, where she says a lot of foul language regarding Darla. Thankfully, Bertram runs a blender over the words every time she is about to say them.
- Country Mouse: She's originally from Fort Hood, a small town in Texas, and is still adjusting to life in New York.
- Cool Big Sis: She acts as a surrogate protective older sister to the Ross Kids.
- Cute Bruiser: Jessie knows a few military moves that she shows when she subdues Emma's punk boyfriend.
- Cute Clumsy Girl: Likely unintentional, but suffers a lot of slapstick.
- Disproportionate Retribution: She can be very unreasonable to the kids at times.
- Fiery Redhead: She can be aggressive, and threatening, when others push her to her limits.
- Forgotten Anniversary: She initially thought that Tony had forgotten their one-year anniversary, but she was the one who actually had the date wrong.
- The writers seem to have become stuck on her having bad relationships with guys and as Season 1 progressed she seemed more and more like a relationship chaser (possibly a Disneyfied Good Bad Girl or Ethical Slut) than a girl with just enough bad experiences to make her play it safe with Tony. As many relationship stories as she's mentioned, it seems like she dated every single guy in her hometown at least once. The stories are becoming more outlandish as well.
- The whole Failure Is the Only Option angle. Jessie started the show being able to fly helicopters and bragging about winning talent shows; in Season 2 she comes off as being lucky if she manages walk down the hallway without being run over.
- Girly Bruiser: She's pretty feminine, but thanks to her military upbringing, she can easily defend herself or the kids with some well-placed punches.
- Identical Stranger: She's on the receiving end of this in Karate Kid-tastrophe, where Jessie ran into Mr. Moseby himself. After Jessie leaves, Mr. Moseby called Cody on the phone to tell him about her uncanny resemblance to Bailey.
- Improbable Piloting Skills: Jessie is capable of flying a helicopter, as evidenced by the pilot. In a later episode, "We Are So Grounded", she crash-lands a jet in an emergency. She calmly prefaces her aerial antics with "my father taught me how to fly!" She flies a helicopter again in the Austin & Ally Crossover.
- Magical Nanny: A mix of Type I and II. She brings the whole family together, but she also handles the kids whenever they're rambunctious.
- Mama Bear: Don't mess with Jessie's kids. This comes in full force in "We Are So Grounded".Jessie: How dare you scare my kids!
- Military Brat: Her father is in the Marine Corps.
- Ms. Fanservice: It's not hard to see how.
- Not So Different: In "Where's Zuri?" Jessie meets Stuart's "manny" Hudson, the two have completely different methods of how they nanny, but when both Zuri & Stuart go missing, Jessie learns they have nearly the same backstory, even lampshaded.Hudson: I came to New York to become a famous novelist, but then I fell out of a cab and wound up Stuart's nanny, but you wouldn't understand.Jessie: Are you kidding? You're basically me with man hands.
- Also with Mrs. Chesterfield. Both are Fiery Redhead who are mistreated by the kids and have a disturbing history of failed relationships
- Official Couple: With Tony... until they broke up in "Break Up and Shape Up".
- One of the Kids: She's by far the most mature, by age and personality, but she definitely has her moments.
- Ooh, Me Accent's Slipping: In-Universe, Jessie will occasionally slip into a Texas drawl (the character is actually Texan).
- "The Reason You Suck" Speech:
- She lays a pretty good one on Brody in "The Princess and the Pea Brain".
- To "McD" in "Jessie's Big Break" and Simon in "Toy Con". Pretty much expect one of these if there's a sleaze bag trying to pull a fast one on Jessie or her kids.
- Retcon: In seasons 1 and 2, she knew a lot about Harry Potter (at least enough to know that Voldemort doesn't have a nose), but in season 3 she doesn't even know what Quidditch is.
- Series Goal: To become an actress.
- Slapstick Knows No Gender: Jessie takes as much of a beating, possibly more, than Luke and Ravi do.
- Smarter Than You Look: Jessie usually acts like she needs instructions on how to breathe, yet she came straight from Texas as a Straight-A student and can fly a helicopter (among other things).
- Southern-Fried Genius: She was a straight-A student in school.
- Team Mom: To the Ross Kids.
- Took a Level in Dumbass: Jessie has become stupider over the seasons. In the first season, she mentions that she was a straight-A student in high school, and yet, in the fourth season episode "What a Steal," when she's trying to pretend to be a genius to date a good-looking genius guy, she's not able to figure out if any fraction with a denominator of 0 would be undefined.
- Ungrateful Bitch: In "We Are So Grounded," she isn't exactly grateful to Emma for draining the venom out of the bug bite she received with a spork, which had caused her temporary Sanity Slippage; the most she gives Emma for "sporking" her back to health is a deadpan "thank you" and a threat to "do the same" to her someday. Of course, it becomes somewhat more justified when one recalls that Emma's refusal to heed Jessie's and the pilot's warnings to turn off her electronics is exactly what caused their plane to crash in the first place.
- What Happened to the Mouse?: In Bunk'd we get no information as to whether she has succeeded in her Hollywood career or whether she and the Ross family keep in touch. The only information we get is in the first episode of Season 2 when we see that Bertram is still with the Ross family, meaning that Jessie is not yet famous yet.
Portrayed by: Peyton R. List
- All Women Love Shoes: Orders forty pairs of shoes in "Green-Eyed Monsters", to name one of the better examples.
- Big Sister Instinct: To Ravi and Zuri. Not so much with Luke.
- Blonde, Brunette, Redhead: The blonde to Zuri's brunette & Jessie's redhead.
- Brainless Beauty: Subverted. She may act ditzy at times, but is a straight A student.
- Bratty Teenage Daughter: Downplayed. While she's snarky to Jessie, she's still a sweet girl usually easy to get along with. In Karate Kid-tastrophe, this is completely exaggerated.
- Catchphrase: "Idiot", often directed at Luke.
- Character Development: She's shown the most development out of any character in the whole series. She started out as a shallow, snarky, somewhat conceited, but still a Jerk with a Heart of Gold. Over the course of the series, she's learned from her mistakes and has grown up into a hardworking, compassionate, forgiving, borderline Nice Girl. She's easily the nicest character to Bertram and Jessie and tries to help the other characters with their problems. She's even now seeing it's inside that matters as shown with her friendship with Maybelle and how in "Morning Rush" she was going to go out with a nice geeky boy over a self centered guy who was really attractive, during the whole episode she couldn't decide to go out with.
- Cool Big Sis: To Ravi and Zuri. Less so to Luke, since they fight and argue a lot.
- Deadpan Snarker: Sometimes she's snarky towards Jessie or Luke.
- Ditzy Genius: Emma is actually pretty smart, but she also acts rather goofy. Also doubles as a Techno Wizard.
- Dumb Blonde: Downplayed. She's a good student, but sometimes she misses the point.Jessie: That's when he assigned me to... the [chicken] plucking pit.
Emma: You had to pluck chicken eyebrows?
- Expy: Emma has a thing or two in common with London Tipton. They both even like Arturo Vitalli.
- Fangirl: Of Austin, One Direction and sometimes Twilight.
- The Fashionista: Peyton R. List, a Real Life fashionista, mentioned in an interview that Emma's original wardrobe prior to her being hired was cute but somewhat normal compared to Peyton herself. As a result the wardrobe people used Peyton's own style to help make Emma more of a true fashionista. They sometimes collaborate Peyton's clothes with the wardrobe choices for Emma to create even more outfits.
- Friend to All Children: Fondness of younger kids shows up multiple times in the show.
- Hair-Trigger Temper: In Karate Kid-tastrophe.
- Hormone-Addled Teenager: Not to the same degree as Luke, but she's starting to show signs of it.
- Hot-Blooded: Somehow developed this attitude in Karate Kid-tastrophe. You simply just can't calm Emma down.
- Huge School Girl: In "Star Wars", Emma mentions being tall for her age.
- Genki Girl: Usually a bubbly, optimistic, and happy person.
- Girly Bruiser: She isn't exactly Kim Crawford, but she can easily handle her brothers and isn't scared to fight.
- Jerk with a Heart of Gold: She's snarky, shallow and self-centered, but she's a good sister to Ravi and Zuri.
- Loony Fan: Of Austin. Also of Jordan Taylor in "Star Wars".
- Odd Friendship: With Rosie, an edgy, street-like girl of her class.
- Screw the Rules, I Have Money!: Though not to the same extent of Big Bad Mrs. Chesterfield, Emma acts this way from time to time and more than the others, especially in the crossover episode. In fact, if she wasn't rich and pretty, it would've just been super creepy for Austin and friends to stay the night, not to mention dangerous. But since the Ross family is rich, they all but begged to stay in the penthouse.
- She's Got Legs: She has moments of this, particularly in "Take the A-Train, I Think?", "Teacher's Pest" and "Toy Con."
- Shipper on Deck: She supports Jessie and Tony.
- Sibling Rivalry: With Luke. They argue like the typical brother and sister.
- Techno Wizard: She's pretty tech savvy, being able to repair a broken apart cell phone or airplane radio, which are fairly complicated devices that need to be assembled by precise machines or very skilled technicians.
- Token White: Among her siblings (even if excluding Luke is a stretch).
- Took a Level in Kindness: Emma is much kinder in Bunk'd, as she does make an honest effort to do nice things to others, even if they up causing disaster.
Portrayed by: Cameron Boyce
- Aesop Amnesia: No matter how many times he learns to work hard in school, he will go back to being a slacker. Even after the finale, Luke promises he will work harder, the first episode of Bunk'd made it clear Luke does not make good on his promise, as he had to go to summer school. When he visits in Bunk'd, we find out he's been getting straight A's. Looks like the lack of siblings did wonders for him.
- All Men Are Perverts: There's a running gag with him hitting on Jessie.
- Aloof Big Brother: To Ravi (and, to a degree, Zuri) at first, but he's getting better.
- Ambiguously Brown: His ethnicity isn't confirmed, but there are several hints that he's meant to be Latino. His actor Cameron Boyce is half black and half Jewish.
- Annoying Younger Sibling: To his older sister Emma who is often annoyed by Luke's habits.
- Berserk Button: Played with. Books make him go ballistic. It's revealed in Bunk'd, that Ravi gifted Luke a giant dictionary, and it caused Luke to hit him in the head with it. However, Luke wasn't entirely mad—he enjoyed doing it.
- Big Brother Instinct: After being embarrassed of Ravi for most of Are You Cooler Than a Fifth Grader? Luke finally develop this when Dale Davenport tries to pummel Ravi.Luke: Leave my little brother alone!
- Book Dumb: Oh so much. He can't even spell "Summer School".
- Brilliant, but Lazy: In the episode Identity Thief it is revealed that when Luke puts effort into school he's quite intelligent.
- Comedic Underwear Exposure: In the episode "Trashin Fashion", Jessie pulls a thread that unravels his pants, revealing a pair of bright green panda boxers.
- The Cast Show Off: Cameron Boyce is a talented break dancer in real life.
- Deadpan Snarker: Up there with the best of them. Probably the snarkiest of all the Ross kids, along with Zuri.
- Dumbass Teenage Son: If preteen is close enough.
- Dumb Jock: He's an athlete at school and isn't the sharpest tool in the shed.
- Handsome Lech: Cute, charismatic, and shamelessly flirty.
- Happily Adopted: Adopted by the Ross family when he was five years old.
- Hormone-Addled Teenager: He loves flirting with girls, mostly Jessie.
- Jerk with a Heart of Gold: Even if he's mischievous and often insults or pranks Ravi, he cares for him deep down.
- Kid-anova: A self-proclaimed Chick Magnet.
- Latin Lover: Well, he tries to be a ladies' man.
- Little Boy Seeks Big Girl: Towards Jessie, towards Shaylee Michaels in "Jessie's Big Break", and later towards Bryn Breitbart in "Diary of a Mad Newswoman".
- Lovable Sex Maniac: He's just a preteen obsessed with girls, so it's Played for Laughs.
- Manipulative Bastard: Luke seems to have no qualms about manipulating his sibling to get what he wants.
- Never My Fault: Luke and Zuri blame the jeep incident in GI Jessie on Ravi, for not trying to stop them. Shown again in "Help Not Wanted" when Zuri and Luke blame Jessie for their irresponsible spending even though she immediately called them out on their spending habits when she saw the bills.
- The Prankster: He loves pulling pranks, especially on Ravi.
- Sensitive Guy and Manly Man: The Manly Man to Ravi's Sensitive Guy.
- Sibling Rivalry: With Emma. They argue like the typical brother and sister.
- Stalker with a Crush: He gets creepy when it's revealed by Luke that he saved a DVD video of Jessie hanging out at the beach and that he placed a camera in Jessie's room to spy on her.
- Teens Are Short
- Took a Level in Dumbass: Zig-Zagged. He's shown in later seasons to be smart but lazy while at the same time he gets "think pains" and actually feels pain whenever he needs to use his brain.
- Took a Level in Jerkass: Later seasons made him out to be more of a jerk than usual.
- Youthful Freckles: He even lampshades that they can only take him so far.
Portrayed by: Karan Brar
- Adorkable: In contrast to Luke who acts more like a cool guy, Ravi is a nerdy boy who often spends time with his lizard.
- Alliterative Name: Ravi Ross
- Annoying Younger Sibling: Ends up becoming one by making Luke do intellectual things, or trolling him with intellect.
- Bestiality Is Depraved: Played for Laughs in "Capture the Nag," where he outright calls Mrs. Kipling his soul mate.Jessie: Okay, we really need to talk about boundaries between you and that lizard.
- Beware the Nice Ones: When angry, or scared he will often scream in Hindi.
- Bilingual Bonus: Whenever Ravi ends up freaking out in Hindi.
- Bollywood Nerd: He's Indian and the smartest of the Ross kids.
- Butt-Monkey: He has gone from a naive but endearing Indian boy into a stereotypical nerd who is so weak and unpopular, that EVEN his family see him as pathetic. He's been mocked, gotten wedgies, had his underwear exposed, blackmailed with humiliating fates, and the list goes on.
- The Chessmaster: Smart as he's, he can easily manipulate Jessie and his siblings.
- Control Freak: Part of what Ravi's development throughout the series is to not change people or make them conform to his standards. He kept doing this to Luke, and still slips into this tendency towards Jorge in Bunk'd.
- Deadpan Snarker: Surprisingly, he's pretty good at this. For example:Ravi: "Do you know what would make this story more enjoyable? If I did not have a piano string where the sun does not shine."
- Funny Foreigner: Actually avoided, while Ravi does act foreign, most of his jokes aren't ethnicity based, although Zuri does call him Mowgli in the Christmas episode.
- Happily Adopted: An Indian boy adopted by the Ross family.
- Insufferable Genius: Has his moments.Jessie: I found this group you might like. It's called the Intelligency.
Ravi: Oh, I know what Intelligency is. It's a group of kids with genius IQs who do not wish to associate themselves with numbskulls.
Jessie: Hey, just 'cuz someone isn't a genius doesn't make them a numbskull!
Ravi: Actually, according to theories in phrenology, diminished cranial sensitivity is directly related to stupidity.
Jessie: Yeah, you're gonna fit right in.
- Karmic Trickster: Whenever Luke goes too far. This is shown when Ravi tries to get revenge on Luke for playing constant practical jokes on him.
- Naïve Newcomer: Hes the new kid in the family and according to Jessie, the others haven't corrupted him yet.
- Nice Guy: Usually cheerful and friendly.
- Overprotective Dad: To Mrs. Kipling's hatchlings.
- Savvy Guy, Energetic Girl: The Savvy Guy to Zuri's Energetic Girl.
- Sensitive Guy and Manly Man: The Sensitive Guy to Luke's Manly Man.
- Took a Level in Jerkass: He begins mocking everyone's intelligence post-season 2.
- Unaffected by Spice: Because of his background, he's accustomed to eating extremely hot foods. In "Are You Cooler Than a Fifth Grader?", Ravi is able to get rid of a bully by letting him steal and eat his lunch: a sandwich with Indian dragonfire peppers. The bully screams and runs away in agony, while Ravi eats a whole pepper without even flinching.Luke: How do you do that without screaming in pain?
Ravi: Where I come from, people sleep on beds of nails and walk on hot coals. This is nothing!
- Wise Beyond Their Years: Smart enough to even teach his own yoga class.
Portrayed by: Skai Jackson
- Annoying Younger Sibling: Mostly to Luke, but she also annoys Emma or Ravi on occasion.
- Blonde, Brunette, Redhead: The brunette to Emma's blonde & Jessie's redhead.
- Bratty Half-Pint: Moreso in later seasons.
- Cheerful Child: A very playful little girl.
- Child Prodigy: She's really, really good at chess. She nearly beat a local champion, but she threw the match so he could win the prize. (A trip to Paris to see his family.)
- Cloudcuckoolander: Initially a Ms. Imagination who has a hard time separating fact from fiction, brought to light by her array of imaginary friends and pets.
- Cute Bruiser: Zuri once took down both Jessie and Luke in about as many seconds. Took down Ravi by technicality when he surrendered himself to the floor.
- Distaff Counterpart: Zuri is basically the female version of Luke.
- Girls Love Stuffed Animals: Has many stuffed animals.
- Girly Bruiser: She loves stuffed animals and the colour pink, but she will flip you if you fight her for the TV remote.
- Happily Adopted: Zuri was adopted at birth from Uganda.
- Hidden Depths: It's implied fairly often that she likes country music.
- Intergenerational Friendship: With Nana Banana, an adult woman who lives in the same apartment building as the Ross Family.
- Little Miss Badass: The youngest of Ross siblings and a Cute Bruiser.
- Mouthy Kid: The youngest of the Ross kids and often snarky towards the older characters.
- Ms. Imagination: She still has some of it even in her pre-teen stage.
- Sassy Black Woman: A younger example, but she fits otherwise.
- Savvy Guy, Energetic Girl: The Energetic Girl to Ravi's Savvy Guy.
- Shipper on Deck: She supports Jessie and Tony.
- Tiny Tyrannical Girl: Downplayed but she can be bossy at times.
- Took a Level in Jerkass: She's showing some signs of it. In season 1 she was kind of snarky but genuinely playful and nice. In season 2 she started acting a lot more greedy and bratty.
- Young Entrepreneur: In "Say Yes to the Messy Dress" and "Why Do Foils Fall In Love?".
Portrayed by: Kevin Chamberlin
- Butt-Monkey: Tends to take the most abuse from other characters.
- Camp Straight: Especially in "Make New Friends but Hide the Old".
- Catchphrase: "It's just... so far away," used in a slightly whiny voice to refer to something he doesn't want to get up to do. Which is most things.
- Child Hater: Though not to the extent of Mrs. Chesterfield.
- Deadpan Snarker: Of the Servile Snarker variety, as the family's sarcastic butler.
- The Dog Bites Back: In some episodes, he does end up getting even with the Ross kids.
- Grumpy Bear: Often seen whining or complaining.
- Hidden Depths: He loves opera and he can sure belt out a tune as seen in the Christmas episode.
- Fat Bastard: An overweight man who tends to be grumpy and doesn't seem to like children.
- Jerk with a Heart of Gold: Even though he usually doesn't show it, he actually cares for Jessie and the kids.
- Jerkass Has a Point: Even though he's aloof and doesn't show that he cares for the kids, there are times he rightfully calls out the kids for not caring for her happiness, or when he steps up and becomes the adult.
- Lazy Bum: He really doesn't like doing housework. Turns out Christina knew all along. She and the kids happen to find his laziness entertaining.
- Manchild: He can be just as immature as the kids.
- Out-of-Character Moment: Whenever he does work, it usually means that Morgan or Christina are home.
- Professional Butt-Kisser: He shills Morgan and Christina like you wouldn't know.
- Running Gag: Wanting to do something, but not doing it because the object he is reaching for is too far. Once he wanted to sign a note, but since the pen on the nearby coffee table wasn't within arm's reach, he was too lazy to get it.
- Trademark Favorite Food: Cheese, to the point where he is a specialist on identifying rare brands of cheese.
- Ultimate Job Security: Played with—he hardly does his job, could've been fired a long time ago and knows it, but Christina found out a long time ago but never fired him. Why? Because the kids are fond of him and she doesn't want to upset them by firing him, and she's not upset when she tells him.
- Action Pet: To an extent. Kipling has saved Christmas decorations, taken care of venomous spiders, and smacked people with her tail.
- Cool Pet: A 7-foot Asian Water Monitor Lizard.
- Reptiles Are Abhorrent: Subverted. Mr. Kipling seems to be bad, until you get to know him.
- Samus Is a Girl: Mr. Kipling is really a Mrs. Kipling, as revealed in the Season 1 finale.
- Team Pet: The Ross family's house pet.
- Your Tomcat Is Pregnant: In the season 1 finale, Mr. Kipling lays a clutch of eggs and is thus renamed "Mrs. Kipling".
Portrayed by: Chris Galya
- Crazy Jealous Guy: A downplayed version, but "Green-Eyed Monsters" shows that he gets easily jealous over Jessie being friends with Officer Petey.
- The Ditz: Tony is a slight airhead, but still really funny.
- Dogged Nice Guy: Tony has been helping Jessie in any way possible throughout the show.
- Knows a Guy Who Knows a Guy: In one episode, Zuri mentioned that "Tony knows a guy" with regards to bringing in a Porta-potty to her room to help Jessie overcome her fear.
- Love Interest: To Jessie. They ended the series as a couple.
- Official Couple: With Jessie... until they broke up in "Break Up and Shape Up". They get back together in Ghostest With The Mostest, when Jessie learns that Tony has a dream of his own.
- Satellite Love Interest: Though, he is greatly defined for also being The Reliable One to Jessie, especially helping out in certain situations, getting things that Jessie needs, etc.
Mrs. Rhoda Chesterfield
Portrayed by: Carolyn Hennesy
- Abhorrent Admirer: She has a crush on Bertram, although he is repulsed by her.
- Abusive Mom: Is implied to be somewhat abusive towards her daughter Cassandra, Played for Laughs of course.
- Arch-Enemy: The archenemy to Jessie. She has it out for Jessie for no reason, trying to put her down and get rid of her.
- Big Bad Ensemble: One of the recurring antagonists along with Nanny Agatha.
- Catchphrase: Mrs. Chesterfield always calls Zuri "strange little girl".
- Child Hater: She hates the Ross kids.
- Cruella to Animals: Implied but downplayed. She has no problems with her dog, Zeus, but she wanted to get rid of Mrs. Kipling out of spite. However, it was believed she was going to kill off the baby lizards, but she was simply just getting rid of them in a way that would not be cruel in the public's eyes.
- Deadpan Snarker: Has her moments of sarcasm.
- Dirty Old Woman: Has a habit of coming incredibly strongly towards younger, attractive or simply men she desires, to the point of outright sexual harassing them (and implies it happens so often she considers them suing her for it nothing more than playing hard to get).
- Even Evil Has Loved Ones: Her dog, though it's not clear as to the full extent of her care for her. Zeus, however, clearly does not return the sentiment.
- Even Evil Has Standards: She was clearly appalled by Jessie when she thought Jessie was framing the kids for something she did. She even points this out.
- Evil Cannot Comprehend Good: She was shocked that cutting her son off would't stop him from being with Jessie.
- Evil Redhead: Though a throwaway gag reveals that she's not a natural redhead.
- For the Evulz: When she destroys Luke's ball, Luke says it was mean, and her response? She just says "Thank You".
- Gold Digger: She married her first husband because he was rich and got all his money, and repeated that process over and over again.
- Go-Karting with Bowser: Zuri and Emma spend a civil dinner with her just to see Jessie and Brooks squirm. The only reason she let them eat with her is because they all don't want Jessie to be with Brooks.
- Hate Sink: She's just so despicable and unsympathetic to the point of kicking the dog by insulting and making Zuri's, Ravi's and Luke's lives miserable for no particular reason. Furthermore, she goes out her way to do anything it takes to get Jessie fired, even when Jessie hardly does anything to her.
- Informed Flaw: Is commonly described by others as if she is ancient and hideous, while Carolyn Hennesy is a quite attractive gracefully aged woman.
- Jerkass: Generally cruel, mean, and unpleasant.
- Kick the Dog: She goes out of her way to antagonize Jessie and the kids for petty reasons. Comes full force in Between Swoon and New York City. She finds out her son Brooks is dating Jessie, and what does she do? Cuts him off, cancels his credit cards and watches Brooks and Jessie suffer as they can't find a way to pay.
- Lack of Empathy: She doesn't care for anything but herself.
- Laser-Guided Karma: She finally gets it in Four Broke Kids, Ravi found illegal deductions in her email, alerted the authorities, and lost her fortune. Chesterfield really had it coming.
- Malicious Misnaming: Refers to Jessie as "Bessie" and Emma as "Jemma". Probably does this on purpose.
- Not-So-Harmless Villain: Her son Brooks doesn't find her vicious, but she reveals that she did really terrible things to her ex-husbands when she did not get her way.
- Pet the Dog:
- Rich Bitch: A rich woman who lives directly under the Ross family's apartment.
- Serial Spouse: It's revealed she's been married six times.
Morgan and Christina Ross
Portrayed by: Charles Esten and Christina Moore
- And Starring: "Charles Esten as Morgan Ross".
- Chuck Cunningham Syndrome: Only Christina returns home in the finale, and Morgan is nowhere to be seen after "Gotcha Day".
- Follow in My Footsteps: In Bunk'd, it's mentioned Christina sent Emma to camp Kikiwaka in the hopes that Emma will live up to be a great counselor like she was. In turn, Emma WANTS to make her proud, but doesn't feel she can live up to that dream.
- I Choose to Stay: In the series finale, Christina decides to become a stay-at-home mom so Jessie can star on her show.
- Invisible Parents: Semi-Averted. We do see them, but not very often. It ends up being lampshaded in the finale by Bertram, and when it became clear the kids would outgrow their nanny, Christina decides from now on, she needs to be there for them more.
- One of the Kids: Morgan, who's usually seen playing with the presents he brings for his kids.
Portrayed by: Jennifer Veal
- Big Bad Ensemble: One of the recurring antagonists along with Mrs. Chesterfield.
- Even Evil Has Standards: She's a big-time bitch, yes, but even she finds her twin sister Angela despicable.
- Evil Brit: An ugly and arrogant British nanny.
- Evil Counterpart: To Jessie, where as Jessie is sweet and compassionate and doesn't try to compete with other Nannies, Agatha is cruel and always down for a competition.
- Expy: She resembles Nanny McPhee, but with none of her nice qualities.
- Gonk: She is shown to be ugly, what with her snaggletooth and huge wart.
- The Rival: A rival nanny to Jessie.
"Creepy" Connie Thompson
Portrayed by: Sierra McCormick
- And Now You Must Marry Me: In her third appearance, she tries to force Luke to marry her. Complete with Luke getting dragged to the "altar" while bound in a wheelbarrow lift.
- Ax-Crazy: While in her first appearance, she is much more creepy than crazy, she is full blown Ax-Crazy Stalker with a Crush in her next appearance. Connie turns it Up to Eleven in "Creepy Connie 3: The Creepening" including hiring an actress in order to dupe Luke. In order to avoid paying said actress, Connie kidnaps her. Connie herself confirmed she's had at least one police line-up. And her uncle confirms her multiple(!) restraining orders in "Creepy Connie 3"
- Clingy Jealous Girl: She wants Luke all to herself and she sees Jessie as competition that she has to get rid of, even though Jessie has made clear she has no feelings for Luke.
- Creepy Child: She has no qualms with injuring people or tying people up to get what she wants. She's called "Creepy" Connie for a reason...
- Cute and Psycho: She's a blonde cute girl but also insane and dangerous.
- Expy: She's got all of Olive's traits but in an evil way. Granted, they both share the same actress.
- Fangirl: Of Harry Potter.
- Knife Nut: She briefly mentions having a knife collection.
- Knight of Cerebus: She's way worse than Rhoda Chesterfield and Agatha combined.
- Mad Love: She loves Luke and she will do anything to be with him, including stalking and threatening and/or hurting him or anyone that gets in her way. Luke makes it clear several times that he only finds her creepy and tries to run away from her, but nothing he says or does will make Connie accept he isn't interested in her.
- Motive Decay: In her first appearance, her primary goal was to date Luke and moved on after she accepted she and him had nothing in common, her second appearance she was injuring her classmates solely to kiss Luke, by her third appearance her goal was to marry Luke.
- Murder the Hypotenuse: A non-lethal version, but close to it. Her second episode deals with her attempting to get the role of Luke's lover in the school play. How does she do this? By taking out her competition, of course! The first girl she pushes down a flight of stairs, putting her in a full body cast, she welds a wrench to the next girl's braces, and attempts to crush the final girl with a sandbag!
- Not Good with Rejection: She takes Luke's lack of interest very poorly, to say the least.
- Stalker with a Crush: She takes pictures of Luke and video-tapes him in class, sends him over forty text messages over the course of a day, breaks into his house and owns a Luke doll.
- Teen Genius: This was why Jessie had her tutor Luke.
- Troubling Unchildlike Behavior: Threatens Luke with a flamethrower, to name the best example.
- Vile Villain, Saccharine Show
- Yandere: To Luke. In her 2nd episode, "Creepy Connie's Curtain Call," she went apeshit over Luke in the play just so she can kiss him. On her 3rd time? She brings out a whole wedding for her and Luke (Luke of course, gets bound in a wheelbarrow lift on a rope), with those who tried to stop her also bound to their chairs TO WITNESS THEIR WEDDING!
Portrayed by: Joey Richter
- Birds of a Feather: A platonic version with Jessie.
- Cloudcuckoolander: He is known for his improv obsession.
- Police Are Useless: He means well, but we have yet to see him do any police work.
Portrayed by: Kelly Gould
- Deadpan Snarker: She has a cynical humor.
- Green-Eyed Monster: Admits to Emma that her Kick the Dog moment was an act of jealousy.
- Jerk with a Heart of Gold: She feels bad when she realizes how her Kick the Dog moment affected Emma and comes to the penthouse to apologize.
- Kick the Dog: She gets Emma to help her with a project, but intentionally makes her look stupid in front of the class.
- New Transfer Student: She begins attending Emma's school in "Make New Friends, but Hide The Old".
- Taking the Bullet: Or rather, cheese. When Bryn responds to Emma with a Redemption Rejection, she decides to throw cheese and nachos to her, but instead, Rosie takes the hit.
- Tomboy and Girly Girl: Tomboy to Emma's Girly Girl.
Portrayed by: Katherine McNamara
- Blatant Lies: She tells people she's Danish royalty. She doesn't even have a European accent. Her parents actually run a toilet paper empire.
- For the Evulz: Basically why Bryn was trying to turn Emma's friends against her.
- Green-Eyed Monster: She's jealous of Emma because of her status and popularity.
- HeelFace Turn: Subverted in "Diary of A Mad Newswoman": It was all an act to take over the school news broadcast.
- Manipulative Bitch: She can manipulate anyone without any faults.
- Redemption Rejection: When the truth is discovered about her, Emma offers to be her friend if she'll agree to start being nicer. Her response is to fling nachos at Emma.
- Rich Bitch: However, her parents run a toilet paper empire, which isn't saying much.
- Take That!: Far-right Americans were furious over the name of this character, thinking it was yet another attempt from the left to intentionally offend them, claiming the name Breitbart was taken directly from the late Conservative blogger, Andrew Breitbart.
- Unreliable Expositor: Her backstory is a lie just to gain the loyalty of Emma's friends.
Portrayed by: Josie Totahnote
- Abhorrent Admirer: For Zuri, until he proved himself not to be useless after all.
- Dogged Nice Guy: Towards Zuri. He sends her flowers, asks her out on dates, and calls her by sweet nicknames.
- Spear Counterpart: Is basically Creepy Connie without the strength or Harry Potter references.
- Stalker with a Crush: He has a huge crush on Zuri. He briefly becomes this to Emma, when he pretends to fall in love with her in order to make Zuri jealous.
Portrayed by: Jennifer Veal
- Bitch in Sheep's Clothing: Appears as a kind, doting nanny, the opposite of Agatha...useful to get the kids to prefer her over Jessie.
- Evil Brit: Since she's Agatha's twin after all.
- Evil Twin: Well... eviler anyway. Even Agatha finds her despicable.
- Face of an Angel, Mind of a Demon: She's gorgeous, especially in comparison to Agatha, but is actually even more evil and cruel than her twin sister, trying to manipulate events to get Jessie fired so she could take her job as nanny; even Agatha herself finds her monstrous.
Portrayed by: Maia Mitchell
- Awesome Aussie: When she was a child, she played outside in the outback and used a live scorpion as a pacifier. As an adult, she wrestles crocodiles/monitor lizards for fun, can terrify Mrs Kipling by hissing and when the monitor lizard bites her, she bites back! She also knows how to make her breath toxic enough to render a person unconscious.
- Outnumbered Sibling: She has eight brothers.
- Raised by Dudes: Shaylee comments that she built up her strength to be just as formidable as her brothers.
Portrayed by: JoAnne Worley