Characters: Jessie

Main Characters

Jessie Prescott

Portrayed by: Debby Ryan

  • Action Girl: Probably the most capable fighter in the series. Justified since her military dad taught her.
  • Adorkable
  • 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.
  • Butt Monkey
  • Buxom Is Better
  • Cain and Abel: Abel to her stepsister Darla's Cain.
  • 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: To Emma, Ravi, and Zuri.
  • Cute Bruiser
  • Cute Clumsy Girl: Likely unintentional, though.
  • Deadpan Snarker
  • Disproportionate Retribution: She can be very unreasonable to the kids at times.
  • Expy: Of Bailey, to the point where most fans consider them the exact same character.
  • Fiery Redhead
  • Forgotten Anniversary: She initially thought that Tony had forgotten their one-year anniversary, but she was the one who actually had the date wrong.
  • Flanderization: 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.
    • Also 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!"
  • The Leader
  • 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
  • Ms. Fanservice
  • 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.
  • Obfuscating Stupidity: She came straight from Texas as a Straight-A student and can fly a helicopter (among other things), yet she usually acts like she needs instructions on how to breathe.
  • 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).
  • Red-Headed Heroine
  • "The Reason You Suck" Speech: She lays a pretty good one on Brody in "The Princess and the Pea Brain".
    • And again 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.
  • She's Got Legs
  • Slapstick Knows No Gender: Jessie takes as much of a beating, possibly more, than Luke and Ravi do.
  • Significant Green-Eyed Redhead
  • Southern-Fried Genius: She was a straight-A student in school.
  • Team Mom
  • 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.

Emma Ross

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.
  • Aloof Big Sister: To Luke.
  • 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: Well, "brainless" is a bit of a stretch. See Dumb Blonde & Genius Ditz.
  • 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.
  • Brilliant, but Lazy
  • 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.
  • Daddy's Girl
  • Deadpan Snarker
  • 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.
  • Hair-Trigger Temper: In Karate Kid-tastrophe.
  • 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
  • Girly Bruiser: She isn't exactly Kim Crawford, but she can easily handle her brothers and isn't scared to fight.
  • Hormone-Addled Teenager: Not to the same degree as Luke, but she's starting to show signs of it.
  • Jerk with a Heart of Gold: She's snarky, shallow and self-centered, but she's a good sister to Ravi and Zuri.
  • The Lancer
  • Loony Fan: Of Austin.
    • And Jordan Taylor in "Star Wars".
  • Ms. Fanservice: On occasion.
  • Narcissist
  • Odd Friendship: With Rosie.
  • Phoneaholic Teenager
  • 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
  • Shipper on Deck: For Jessie and Tony.
  • Sibling Rivalry: With Luke.
  • Spoiled Sweet: Emma is a classic example as she could easily be an Alpha Bitch, but has proved on numerous occasions that she is far from being one. She is still spoiled and pampered nonetheless.
  • 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).

Luke Ross

Portrayed by: Cameron Boyce

Ravi Ross

Portrayed by: Karan Brar

Zuri Ross

Portrayed by: Skai Jackson

Bertram Winkle

Portrayed by: Kevin Chamberlin

Mr(s). Kipling

Recurring Characters

Tony Ciccolini

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
  • Dogged Nice Guy
  • 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
  • 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: To Bertram.
  • Abusive Mom: Is implied to be somewhat abusive towards her daughter Cassandra, Played for Laughs of course.
  • Affably Evil: Only towards Emma, though.
  • 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: With Nanny Agatha.
  • Card-Carrying Villain
  • Catch Phrase: Mrs. Chesterfield always calls Zuri "strange little girl".
  • Child Hater
  • 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.
  • 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".
  • 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: Moreso than Zuri.
  • 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.
  • Never My Fault
  • 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: Putting Ravi's lizards in a lizard sanctuary, though according to her, she just did it for the good PR.
    • She also finally excepts her son's choice to marry Jessie.
  • Rich Bitch
  • Screw the Rules, I Have Money!

Morgan and Christina Ross

Portrayed by: Charles Esten and Christina Moore

  • And Starring: "Charles Esten as Morgan Ross".
  • Bumbling Dad: Morgan.
  • 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.

Nanny Agatha

Portrayed by: Jennifer Veal

"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"
  • Blondes Are Evil
  • 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
  • Cute but Cacophonic
  • 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!

Officer Petey

Portrayed by: Joey Richter


Portrayed by: Kelly Gould

Bryn Breitbart

Portrayed by: Katherine McNamara

  • Alliterative Name
  • Alpha Bitch
  • Big Bad Wannabe
  • 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.
  • Devil in Plain Sight
  • 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.
  • Heel-Face Turn: Subverted in "Diary of A Mad Newswoman": It was all an act to take over the school news broadcast.
  • Kick the Dog
  • Obviously Evil
  • 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.

Stewart Wooten

Portrayed by: J. J. Totah

Millie the Mermaid

One-Shot Characters


Portrayed by: Jennifer Veal

Nana Banana

Portrayed by: JoAnne Worley

Darla Shannon

Portrayed by: Molly Burnett