Babysitter's Nightmare

Dad: (holding his empty wallet after paying Rosalyn) You're sure no one else in this town will agree to babysit Calvin?

Mom: Maybe you would like to spend a week on the phone!

— Calvin and Hobbes

Some children aren't satisfied with just being bratty. Oh, no, that's too simple. They make it their personal mission to systematically drive away every single babysitter, nanny, tutor, caretaker, teacher, mentor, or other person their beleaguered parents hire to look after them. One after another, they leave the house (some in tears), never to return. Eventually the kid's reputation is so terrible that absolutely no one in town is willing to babysit them unless the little monster's parents are offering exorbitant amounts of money, and sometimes not even then.

In stories where the babysitter is the protagonist, they're likely to be drawn to the job by the promise of said exorbitant amount of money. They might balk after being told horror stories about the kid by previous babysitters, but decide that putting up with the kid can't possibly be that awful—and besides, they really need that money. They're always Instantly Proven Wrong, but if they can survive a night with the kid, the reward will be worth it.

To make things even harder, Babysitter's Nightmares frequently come in packs; families with several children, especially Trickster Twins, are likely to qualify for this trope. For obvious reasons, multiple children are harder to take care of than a single child, and one strong-willed child can easily railroad their siblings into going along with making the babysitter's night a complete hell.

Sometimes, the child turns out to be misbehaving because of something else that is going on in their life, such as abuse, neglect, bullying, or their parents getting a divorce (a particularly common scenario is the kid acting out because their parents never pay attention to them and leave them with babysitters all the time). A caring babysitter might try to help the child with that problem, which can lead to a deeper understanding between the two of them.

Compare Pity the Kidnapper, in which kidnappers may seriously regret taking a rich man's child for ransom. Exemplified in O. Henry's short story "The Ransom of Red Chief", where two rather dim rogues found the family refused to pay to get their brat back.

Since Tropes Are Flexible, this trope can apply to similar situations that don't necessarily involve babysitting, such as a student no teacher wants to have in their classroom, or a badly behaved, destructive pet that no one wants to pet-sit.

The child in question may have Pushover Parents (or Abusive Parents or Neglectful Parents in the "kid misbehaving because of their crappy home life" version). Sub-trope of Bratty Half-Pint, and possibly Enfant Terrible, Spoiled Brat, Creepy Child, and Lonely Rich Kid. Related to Badly Battered Babysitter, Babysitting Episode, and Expelled from Every Other School. If the babysitter actually manages to tame the tiny terror, the result might be a Babysitter Friendship. They might be an Annoyingly Repetitive Child.

Examples:

Anime

• Daltanious: Kento is this to Dr. Earl. As the pilot of Daltanious and future Emperor of Helios, Earl tries to get the boy to take his duties seriously, only to be rebuffed and mocked each time. Kento addresses Earl as "Old Man" whenever he's speaking to him and often responds to him with "whatever!"^note "なぁんたること!" (Naantarukoto!) In contrast, Kento's father, Prince Harlin/Hayato Tate, was an absolute joy for Earl to teach and raise.

Comic Books

• Animaniacs had Katie Kaboom hired to babysit a Calvin expy that naturally was this. "Alvin's" parents thought Katie's family would never speak to them again. But this being Katie Kaboom, instead it's Alvin's family who will definitely cut relations - while ironically the boy calmed down for finding it cool that he literally made a monster out of his babysitter.

Comic Strips

• Calvin and Hobbes: No one in town will babysit Calvin except Rosalyn, and the only thing that makes her stay is the money she extorts from Calvin's parents. One time, Calvin begged his mom to call another babysitter after finding out he was getting Rosalyn, and her answer was that she called eight people already and Rosalyn was the only one who would do it (and mentions someone named Amy, who just laughed when Calvin's mom called her). Then averted in Rosalyn's final appearance: after she genuinely manages to connect with him and his unique perspective and makes a deal with mutually acceptable terms, she manages to not only get out unscathed but both have a pleasant evening and Calvin even does his homework, a turn of events his parents flatly refuse to believe.
• Dennis the Menace (US): Dennis has proven to be such a terror to every babysitter watching him that no babysitter has volunteered to look after him a second time. It has gotten to the point that Alice and Henry are up to "Z" in the phone book.
  • If you're wondering how terrible Dennis is to his sitters look no further than one strip where Dennis is in a cowboy outfit and has somehow Bound and Gagged his sitter to a chair! Saying "You knew this job was dangerous when you took it!"

Films — Animation

• Soul: 22 has had numerous mentors who tried to help her find her "spark", but ended up driving all of them away with her sassy attitude. She's doing this because she's subconsciously afraid that she's not good enough for life on Earth, so she pushes away anyone who tries to help her.

Films — Live-Action

• The Boy: The Heelshires have hired several nannies over the years for their "son", Brahms, but none of them ever stay. It's implied he eventually kills the nannies off after they somehow upset him too much.
• Mary Poppins begins with the most recent nanny of the Banks family storming out of the house, refusing to have anything to do with watching Jane and Michael ever again. She's indicated to just be the latest in a series of nannies who have walked out on the family.
• Nanny McPhee: The seven Brown children are such terrors that they take pride in having scared away 17 different nannies, each sooner than the last. The most recent being Nanny Whetstone, the strictest, toughest, and most fearless Nanny in all the land, who fled the Brown residence in 3 days, 8 hours, and 47 minutes, the final straw being the children tricking her into thinking that they had eaten the baby.
• Problem Child: Junior is characterized as a holy terror through this trope, being passed from foster family to foster family before winding up in the care of an orphan home run by nuns. This is before he meet the Healys, and the man who would become his dad.

Literature

• The Baby-Sitters Club: The series has many examples. In particular, new children, who are introduced in different books, often start off as insufferable (the Feldman children, the Delaney children, Rosie Wilder, the Arnold twins, Betsy Sobak, etc.) but usually get better thanks to Character Development. However, there are some examples who are consistently seen as nightmares throughout the series, like Jenny Prezzioso or Jackie Rodowsky, who are recurring characters and nobody ever wants to babysit them. (Unlike most examples of this trope, Jackie isn't a brat and doesn't mean to cause trouble. He's just so hopelessly clumsy and accident-prone that the sitters privately refer to him as the "Walking Disaster.")
• Fire & Blood: Princess Saera Targaryen was a Royal Brat of epic proportions who had half a dozen septas (the Westerosi equivalents of nuns) and as many bedmaids before she was 13. She didn't improve with age and would grow up to be a Hard-Drinking Party Girl.
• Horowitz Horror: In "Harriet's Horrible Dream", spoiled rich girl Harriet is proud of the fact that she's managed to get four nannies sacked from her family's house. The last one only lasted three weeks.
• We Need to Talk About Kevin: As a baby, Kevin drives his nanny away by pulling her hair, tearing up her silk scarf and throwing his toys and food all over the floor. As a toddler, he's such a terror to the other kids in his playgroup that the other mothers start making excuses to pull their children out of it, eventually forming a new, Kevin-less one without telling his mother Eva.

Live-Action TV

• Law & Order: Special Victims Unit: In the episode "Glasgowman's Wrath", Perry is a mentally unstable teenager who is said to have gone through a lot of babysitters. She ends up being involved in a crime where she tried to sacrifice Zoe, her best friend's little sister, to Glasgowman (a parody of Slender Man).
• Malcolm in the Middle: In the episode "Water Park," the family is getting ready to go to a water park, with the exception of Francis since he's at Military School, and Dewey who has an ear infection. In the latter's case, Hal is seen talking on the phone to a potential babysitter, and promising that they'll be taking of "just the little one," which is when Malcolm explains that they had issues with babysitters in the past: Baby Francis bit the finger of an elderly sitter; a babysitter ran after the boys showed her something horrifying/disgusting; and Malcolm and Reese locked a guy in closet and listened to him having a panic attack that was induced by his claustrophobia. Malcolm reflects on the last incident and tells the audience "I'm beginning to think it's us."
• The Twilight Zone (2002) episode "The Collection" features a preteen girl named Danielle who has gone through many babysitters in the past. As it turns out, she's not a brat, just immature as a result of being desperately lonely and the child of controlling, overbearing parents. Unfortunately, Danielle thinks that the babysitters who come over are supposed to be her friends forever, and she finds a way to ensure that they stay—namely, permanently transforming them into Barbie dolls that can move, but not speak, and are still entirely conscious.

Theatre

• 35MM: A Musical Exhibition: In the song "Caralee", the narrator babysits a terror of a little girl named Caralee who stabs him in the nuts with scissors and throws her spaghetti on the floor. He ends up paying a crack dealer $50 to take her and celebrates being free of her at the end of the song.

Web Comics

• In the My Little Pony: Friendship Is Magic comic "Fallensitter", nopony in Canterlot will agree to foalsit Twilight because they're terrified of her crazy magic powers. Cadence appears on their doorstep and offers to do it for 175 bits an hour, but Night Light talks her down to 8 bits for the night and two oatsicles from the freezer (and their son Shining Armor's hoof in marriage when they're older).
• The series Forestdale gives us Izabell Carroll, a ten year old tabby cat girl who terrorizes any substitute teacher unfortunate enough to have a class with her in attendance. Most don't even last a day with her before they're sent running to the hills, screaming their heads off after enduring Izabell's antics.

Web Original

• Neopets:
  • In the game The Usul Suspects, you play as Lumi, a teenage babysitter facing off with a water gun against an endless horde of evil baby Usuls armed with ray guns and propeller beanies.
  • In the game Petpetsitter, you are babysitting an increasingly large number of Petpets. You have to clean up the messes they make as they wander around the house and take them to various rooms depending on whether they are hungry, tired, need to use the bathroom, want to go play, or (for Robot Petpets) need to be repaired.

Western Animation

• Adventures of Sonic the Hedgehog: In "Baby Sitter Jitters", Sonic is tasked with babysitting Becky, Bucky, and Chucky, a trio of baby beavers while their father, Cleaver prepares for a barbecue in Sonic's honor for saving Beaverville from being flooded by Dr. Robotnik. As Sonic and Tails soon discover, the Beaver Babies cause trouble for anyone looking after them. When Scratch and Grounder capture the Beaver Babies in an attempt to hold them for ransom, they and Robotnik all suffer great pain from them, even to the point where the Beaver Babies help Sonic foil Robotnik's second attempt to flood Beaverville. At the end of the episode, when Cleaver congratulates Sonic on being the first babysitter able to get his three children under control, he gives him the job of looking after them for the weekend so he and his wife can get out of town before they have a nervous breakdown.
• The Adventures of Super Mario Bros. 3: In "Misadventures in Babysitting", a human boy from Brooklyn, known only as Junior, is prone to misbehaving and causing problems for others. As a result of this reputation, his parents have a hard time finding a babysitter. When the Mario Bros. take a wrong turn through a warp pipe and wind up in Junior's house, Junior's parents mistake them for the babysitters and hire them to look after Junior, paying them in lasagna. When Junior goads the Mario Bros. into playing hide and seek, he finds the warp pipe they went through and winds up in the Mushroom Kingdom, where he teams up with the Koopalings to play pranks on the Mario Bros.. After Junior and the Koopalings trap the Mario Bros. in a cave, the Koopalings repay Junior by tossing him down the Pipe Maze, which they plan to fill with lava. When Junior realizes that the Koopalings aren't just playing games and the Mario Bros. save him, he becomes a lot nicer. When the Mario Bros. return Junior to his house, Junior's parents ask them if they can babysit him again the following Friday. Junior is enthusiastic about this, but the Mario Bros. aren't so much.
• Arthur: In "Arthur Babysits", Arthur is made to babysit the destructive and hyperactive Tibble Twins. Prunella tells Arthur that her sister, Rubella, only babysat for them once and still has nightmares. And indeed, Arthur does have trouble until he manages to Scare 'Em Straight.
• Huey and, to a greater extent, Riley in The Boondocks episode "Home Alone" ended up on a website in the past that tells babysitters to never respond to requests to take care them. Robert resorts to hiring racist jerk Uncle Ruckus, but they drive him away too.
• The Casagrandes: Invoked in the episode "Flight Plan". The Casagrande brothers don't want to be babysat; they want to ride with their parents on a plane, so they drive away all the babysitters. They do this by destroying Mr. Nakamura's antique toys, scaring Miranda, and tricking Maybelle into thinking her celeb crush wants to meet her.
• House of Mouse: A recurring antagonist for Donald Duck is Baby Shelby the Turtle, who he is forced to babysit by Shelby's mother. Donald then quickly is put in a living hell courtesy of Shelby being a relentless daredevil. Most of the shorts end with Shelby's mother asking Donald to look over Shelby again and Donald suffering a nervous breakdown.
• Kim Possible: Kim's father comments that when she was growing up, finding any babysitter willing to watch over her became impossible after a while.
• In Looney Tunes, several Foghorn Leghorn episodes see him trying to babysit various chicks to impress the hens he's romancing. Some play destructive pranks on him, while his most common charge, Egghead Jr., is a Cute Mute whose various science experiments and technical know-how end up leaving Foghorn worse for wear. Unlike most examples, though, Foghorn's bad treatment is usually deserved, as his Know-Nothing Know-It-All and Motor Mouth tendencies make him particularly vulnerable to the kids.
• A variant in The Looney Tunes Show episode, "Father Figures"; when Porky Pig joins the Father Figure program, he is paired with Henery Hawk, who tells him that he goes through father figures like he goes through boxes of chocolate. Porky is determined to prove that he can be a good father figure to Henery, taking him on such activities as watching paint dry and watching grass grow, even though all Henery wants to do is eat chicken, which Porky keeps ignoring because he thinks it's a metaphor for wanting attention. Porky finally realizes that Henery really did want chicken after Henery bites Foghorn Leghorn at the Royal Oaks Glen Oaks Oakwood Oaks Country Club's father/son tennis tournament, resulting in Foghorn becoming hospitalized. When Porky finally serves Henery some chicken near the end of the episode, Henery congratulates him on being the first father figure who didn't give up on him.
• The Loud House: In "Sitting Bull", the four eldest Loud sisters, sick of Lynn's violent nature ruining their babysitting reputations, try to get her to quit by having her watch the Fox quintuplets, the worst kids they've ever sat. They soon feel guilty and try to save her from them, but find that Lynn's rough-and-tumble attitude helps her get along fine with them.
• Rugrats:
  • Discussed in the 1991 series episode "Mommy's Little Assets". Charlotte and Drew both have important business meetings to go to, and need someone to watch Tommy and Angelica^note specifically, since Stu and Didi have gone on vacation, Grandpa Lou has gone fishing, Betty and Howard took Phil and Lil to a big tractor pull, and Chas went to a therapists' convention (and presumably took Chuckie with him). When Charlotte asks Drew if they know any babysitters, Drew tells her they do, but they can never get any of them to look after Angelica a second time.
  • In the 2021 reboot episode, "Nanny Pip", Phil and Lil bring up Angelica's past nannies, one of whom hid in the clothes hamper all afternoon, and another who climbed on the roof and didn't come down. Chuckie even says that no nanny in the world that can handle Angelica. Charlotte also brings up to Didi that one of her nannies quit due to a (nonexistent) pigtail allergy, so she gets Nanny Pip, a robot nanny, to look after Angelica. Nanny Pip manages to get Angelica under her control through a digital unicorn game, where she earns stars to customize her unicorn through good behavior and loses parts of her unicorn for bad behavior. Unfortunately, the new nice Angelica creeps the babies out, so they try to shut Nanny Pip down to get the old Angelica back.
• The Simpsons has numerous examples, mostly having to do with Bart.
  • In "Some Enchanted Evening", Homer and Marge call a babysitting service. When we see the receptionist's office, Bart, Lisa, and Maggie's heads are pasted onto a board with a note reading "NO! NO! NO!" The Simpsons are denied a babysitter until Homer calls under the name of the "Sampson family".
    Receptionist: Those Simpsons. What a bunch of savages. Especially that big ape father.
  • In "The War of the Simpsons", Homer and Marge try to hire a babysitter while they go to a couples retreat. She runs off screaming at the sight of Bart, who tried to run her down with the family car when he was a baby and seems to remember the incident fondly ("Hahaha, come back for more, eh?"), so they decide to have Grampa babysit instead.
  • In "New Kid on the Block", Homer tries to call up Abby, the kids' usual babysitter, but her sister answers instead, telling him that her last encounter with the Simpsons destroyed her.
    Abby: (rocking in her chair) No, Bart, put it down... Put it down, Bart... Bart, put it down...
  • Invoked in "My Sister, My Sitter", in which Bart, outraged that his younger sister is babysitting him, tries to make Lisa's job difficult by being be the worst kid ever, which includes feeding Maggie coffee ice cream and making several prank phone calls, including to emergency services, leading to those hanging up on Lisa when Bart actually injures himself.
  • Exaggerated in "The Changing of the Guardian", in which Homer and Marge decide to search for someone to be their kids' legal guardian in case they die. Once word gets out, the whole town start avoiding them everywhere they go.
  • Exaggerated in "Simpsoncalifragilisticexpiala-Annoyed Grunt-cious", in which the Simpsons hire a Magical Nanny (an Expy of Mary Poppins) and completely destroy her psyche with their relentless dysfunction.
  • As mentioned in the initial trope description, this trope also applies to Bart's schooling—teachers dread having him in class, and only the sour Edna Krabappel has ever shown any ability to get a handle on him (although Marcia Wallace, Mrs. Krabappel's late voice actor, went on the record as saying that the two were more like Friendly Enemies who enjoyed their interactions with one another). In one particularly heartwarming instance, Edna is up for a Teacher of the Year Award, and Bart decides to help by presenting himself to the judges and explaining that anyone who could survive having him in their classroom must be worthy of the title. The committee members can't believe that the infamous Bart is real and immediately hand Edna the prize. And in one episode, she helps Lisa deal with a bullying teacher by weaponizing and unleashing Bart.
• South Park: In "Tsst!", several nannies are hired for the nigh-impossible task of taming Cartman, all to no avail. He sends Nanny Stella from Nanny 911 storming out of the house in a rage by giving her a Breaking Speech about how she's unmarried and childless while her friends have families of their own. He even breaks Supernanny, causing her to become institutionalized while she eats her own shit.
  "It's from Hell... It's from Heeeeeell!"
• A variant in the short, "Rent-A-Friend" from the Tiny Toon Adventures episode, "Rainy Daze"; after having gone through eleven Rent-A-Friends, Montana Max calls the Rent-A-Friend company, who sends over Buster Bunny. Buster is forced to be friendly towards Monty, who mistreats the bunny and has him play with his deadly and destructive toys, but when Monty goes too far, Buster gets his revenge on him. When Monty calls Rent-A-Friend to fire Buster and send someone else over, he finds out that Buster was the only client who willingly volunteered for the job, as Monty's abusive and insensitive behavior (as well as many dangerous toys) has scared all of the other clients away.

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