1. Rebecca De Mornay, The Hand That Rocks The Cradle (1992)
Look past all The Hand That Rocks The Cradle’s grossly exploitative elements—not an easy task, given the molesting obstetrician, the mentally retarded laborer played by Ernie Hudson, and Julianne Moore getting impaled by a collapsing greenhouse—and the film taps into some very basic worries parents have when they invite a nanny into their home. The first, obviously, is “Will my children be safe and well cared-for?” But beyond that, there’s a concern that their kids will be too well cared-for, that the nanny will usurp the mother’s role in the family, driving a wedge between mother and child—and potentially husband and wife. So when Rebecca De Mornay, a super-evil nanny, begins her new gig by slipping into the baby’s room and offering up her own breast, she’s like a wolf marking its territory. When the baby then refuses to take her mother’s milk and De Mornay starts playing Jezebel with daddy, the nightmare becomes real. One point in De Mornay’s favor: Sometimes her psychosis pays dividends. When a little girl under her care complains about being bullied at school, De Mornay tracks the bully down and warns that if he doesn’t stop, she’ll rip his fucking head off.
2-3. John Goodman and William Forsythe, Raising Arizona (1987)
Technically speaking, Goodman and Forsythe’s cons on the lam, Gale and Evelle Snoats, aren’t so much babysitting young Hi Jr. as they are kidnapping him. But like everyone who encounters the suspiciously toddler-aged baby, they fall instantly in love with him, and they plan to make him part of their own family, even including the former Nathan Arizona Jr. on their proposed tri-state crime spree. Unfortunately, in spite of their good intentions, it’s hard not to question the parenting skills of a couple of guys who leave their kid on top of their car and then drive off. Twice. No amount of balloons that blow up into funny shapes can make up for that level of neglect.
4. “The Babysitting Bandit,” The Simpsons (1990)
“Some Enchanted Evening,” the final episode of The Simpsons’ inaugural season, established a now-familiar template for two themes: Marge the unappreciated housewife, and Homer the simultaneously caring, callous, and clueless husband. Attempting to get out of the doghouse, Homer takes Marge to Ye Olde Offramp Inn for a night of passion, entrusting the children to babysitter Ms. Botz (voiced by Penny Marshall). But when the kids catch an episode of America’s Most Armed And Dangerous, they realize “Botz” is Lucille Botzcowski, the notorious Babysitter Bandit, who ties up children while robbing their houses. Soon enough, the kids are tied up on the sofa (watching the mercilessly cutesy Happy Little Elves) as Botzcowski loots the house. With help from Maggie, Bart and Lisa turn the tables on her. But when Homer finds the Babysitter Bandit hog-tied, he automatically assumes his no-good kids have done something horrible, and lets her go. Botzcowski parting advice? “Don’t turn your back on that boy for a second.” She’s a criminal, but she’s right about that one.
5. W.C. Fields, It’s A Gift (1934)
Curmudgeonly comedian W.C. Fields issued the famous admonition to “never work with animals or children,” but in his movies he frequently played hapless family men, dealing with kids either by setting a bad example (as in this clip from The Bank Dick) or by treating them with reckless indifference. In It’s A Gift, Fields plays a grocery-store clerk who agrees to watch toddler Baby Dunk while his mother gossips with a neighbor. Fields' assistant gives the child gooey chocolate to eat and sends him rocketing through the store in a rickety basket. After Baby Dunk yanks open a tub of molasses—“That’s the spreading-est stuff I ever saw in my life,” Fields mumbles—Mrs. Dunk finally gets fed up, accusing Fields of purposefully allowing her child to misbehave. Fields' assistant shrugs and says, “I told him I wouldn’t do it if I was him.”
6. Eda Reiss Merin, Don’t Tell Mom The Babysitter’s Dead (1991)
When she first shuffles to Christina Applegate’s door with her cane, Eda Reiss Merin is a gentle, sweet-voiced old lady who calls all her charges “dear.” But the second Applegate’s mom leaves for the airport, Merin whips out a whistle, furrows her brow, and growls for the “maggots” to get inside and listen to her impossible house rules. Merin is only onscreen and alive for about the first seven minutes of Don’t Tell Mom The Babysitter’s Dead, but in that short span of time she reveals herself as one of the meanest, strictest, least fun child caretakers in cinematic history: She angrily snaps off the TV and assigns an 8-year-old a report on aardvarks, due the next morning. She yanks the teenage son out a car by his ear. She forces the preteen tomboy to wear a frou-frou pink nightmare of a dress. She makes up a complicated chore chart. And she plasters nametags on all the kids that must be worn at all times. Merin is such a “deranged Mary Poppins” that when she dies and Applegate and her siblings decide to wrap her in a California Raisins bedsheet and leave her on a mortuary doorstep, it actually seems like a reasonable decision.
7. Jenny Seagrove, The Guardian (1990)
Speaking of Mary Poppins, it’s probably the film’s fault that when presented with two candidates for a nanny job, one with impeccable references and another with a British accent, families are likely to go with the Brit, because she sounds reassuring and may be magical to boot. So when the prim, attractive Jenny Seagrove shows up at the L.A. home of a couple newly transplanted from Chicago, she seems like the right choice to take care of their newborn. How are they to know that she’s actually a tree-worshipping druid who stays eternally youthful by offering infant sacrifices to a gigantic tree trunk that bleeds the blood of the innocent? Or that she enjoys taking off her clothes and getting fondled by twigs?
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8. Elisabeth Shue, Adventures In Babysitting (1987)
More a victim of circumstance than a bad babysitter, Elisabeth Shue nevertheless comes awfully close to getting her three charges killed again and again. Opting to bring them along on a late-night trip into downtown Chicago to pick up a hysterical friend, she sets in motion a chain of mishaps that includes a run-in with a crazy tow-truck driver, a murderous pursuit by the heads of a car-theft ring, getting in the middle of a knife fight between warring gangs, and—perhaps most terrifying of all—being forced to perform in a club where “nobody leaves without singing the blues.” Yeah, the kids grow up a little and learn how to look after each other and all that crap, but if this were the real world, Chris wouldn’t just be worried about never getting asked to baby-sit again—she’d be in court for criminal negligence.
9. Shelley Winters, Whoever Slew Auntie Roo? (1971)
Once a year, the local orphanage sends their kids over to batty old Shelley Winters’ massive house for a Christmas party, to help her overcome the death of her daughter years before. Winters entertains the children with weird little songs and stories and games, and then returns to her nursery, where she keeps the mummified remains of her daughter. Curtis Harrington’s Whoever Slew Auntie Roo? is a modern riff on Hansel and Gretel—Winters eventually kidnaps one of the orphans, who is rescued by her brother in horrifying fashion—and it pairs well with Harrington’s What’s The Matter With Helen?, also from 1971. Winters stars in Helen as well, as the ruthless proprietress of a school for child actors. Basically, Harrington + Winters = Keep your kids far, far away.
10. Robert Mitchum, The Night Of The Hunter (1955)
When Robert Mitchum’s darkly charismatic preacher swoops in on a widow and her two children, he seems to everyone like a blessing, someone who can cleanse the memory of the woman’s criminal ex-husband and give her family a solid Christian upbringing. The townspeople are bowled over by the stranger’s good manners and rigid decency, and the mother talks herself into believing that this intimidating man of God will bring stability to the household. But the kids aren’t buying it, and behind closed doors, Mitchum drops the façade too. What he’s after is the stolen loot their father (his ex-cellmate) bequeathed to his children before getting shot down by police, and he uses every coercive tactic he can to pry the information from them. He isn’t above arm-twisting a pig-tailed little moppet, nor will he hesitate to stalk the kids when they flee downriver. He preaches about the epic battle between Love and Hate, but in his heart, it’s long been resolved.
11. Paul Rudd, Wet Hot American Summer (2001)
In this exacting send-up of ’80s teen sex comedies, Paul Rudd’s hunky lothario is clearly the last person who should be left in charge of children. Playing the most self-centered camp counselor at a joint stuffed to the gills with self-centered camp counselors, he’s generally too busily on the make to even interact with the campers. But the one time he’s actually responsible for their well-being is under the worst possible conditions, as their lifeguard/boat-safety monitor out on the lake. Unsurprisingly, he’s distracted by a makeout session with his latest conquest and he lets one of his charges drown, but worse, he compounds the crime by taking his victim’s safety buddy out for a spin around the camp and hurling him out of a speeding van, eliminating the only witness to his carelessness.
12. Nancy Loomis, Halloween (1978)
It seems little mean-spirited to judge Nancy Loomis’s poor child-tending skills in John Carpenter’s Halloween, considering her ultimate fate. The trouble is, she happens to be friends with Jamie Lee Curtis, and it’s hard to imagine anyone looking good by comparison. As a babysitter, Curtis is the dream, a surrogate big-sister type who treats her charges with respect while carving jack o’ lanterns and keeping them safe from the boogeyman incarnate. Contrast that with Loomis—while she isn’t actively cruel, babysitting for her is more a way of getting an empty house for some makeout time with her boyfriend. She wanders around in a shirt and underwear, gets herself stuck in a shed in the backyard, and at the first opportunity, dumps the girl she’s watching in the hands of the far more capable Curtis. Casual neglect and horniness aren’t survival traits in a horror film, especially not a proto-slasher like this one, so Loomis pays the ultimate price for her crimes. At least she does the kids a favor by not dying in front of them.
13-15. The fairy godmothers, Sleeping Beauty (1959)
Sure, the squat, winged Flora, Fauna, and Merryweather take on the burden of hiding away baby Aurora in the woods so she can avoid the “dead by your 16th birthday” curse the sorceress Maleficent placed on her. And they do a good job, too… until Princess Aurora’s actual 16th birthday, when they argue pointlessly over her dress so loudly that they draw the attention of Maleficent’s scout-raven, Diablo. Then, at the princess’ birthday party, the fairies drop their guard and allow Aurora to wander into a room where Maleficent is waiting with her Spinning Wheel Of Death. Ladies, you had one job…
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16. “Robositter,” Aqua Teen Hunger Force (2004)
As part of his oddly paternal concern for Meatwad, Frylock creates the Robositter (voiced by Sarah Silverman) to look after him while Frylock is off trying to earn a living. But like so many of Frylock’s inventions, this one backfires. Robositter turns out to be more than just careless and selfish; she’s also filled with homicidal rage, which goes great with the rotating saws she has for hands. After tossing Meatwad around and threatening to unleash the hounds of hell on him, Robositter knocks off four hours early (“robots work twice as fast as humans”), puts on a slutty belly-shirt, and heads to the mall with her friend Sheila (whom she built, along with Sheila’s parents, whom she then made get divorced so Sheila can do anything she wants) so the two of them can “get tattoos right above the crack of our robot asses.” Actually, take away the engineering know-how and the saws, and you pretty much have your average teenage girl.
17. John Candy, Uncle Buck (1989)
When the detached parents of a rich family in suburban Chicago must leave town unexpectedly, they call on Uncle Buck (John Candy), their last choice on a list of potential babysitters. He smokes, drinks, bets on horses, and—worst of all for this couple—has never been responsible enough to hold down a job or keep a girlfriend. He arrives in a smoking beast of a jalopy that backfires whenever idle, he can’t figure out the washing machine, and he embarrasses the hell out of evil teenager Tia. But between lounging on the sofa and vacuuming crumbs from his body, Buck inspires more joy in the kids than their career-obsessed parents do. He even manages to win Tia’s affection when her beret-wearing boyfriend makes it with another girl after Tia refuses to give up her virginity. Of course, Buck does this by binding and gagging the guy, throwing him in the jalopy’s trunk, and then laughing with Tia as they threaten him with a screwdriver and drive a golf ball into the back of his head. Buck’s antics are so adorable that Tia loves her mother again—essentially, the shared secret of kidnapping and endangered chastity heals an entire family.
18. Alicia Silverstone, The Babysitter (1995)
Robert Coover’s 1969 short story “The Babysitter” deftly allows an ordinary occurrence—a young babysitter watching three children and a lot of TV while the parents attend a cocktail party—to branch out into any number of possibilities. The story is told from multiple points of view—the horny middle-aged father, the jilted young ex-boyfriend, the frustrated babysitter, the rambunctious preteen son, the television—and fantasy, imagination, fiction, and reality all meld together, so that sifting out a true linear narrative of what happened that night is not only impossible, but unnecessary. The plot of the 1995 movie adaptation isn’t nearly so ambiguous: Alicia Silverstone is a fairly incompetent babysitter who is also the object of desire and fascination for the kid she’s babysitting, his father, and her ex-boyfriend. It’s fairly easy to distinguish between the various fantasies of the various males (the kid imagining Silverstone asking him to wash her back, the father surprising Silverstone in a bubble bath and being greeted by girlish giggles) and the realities of Silverstone’s drudgery-filled night babysitting (washing dishes, tending to the wailing infant). In most of the fantasy sequences, Silverstone is a naughty babysitter. But otherwise she’s just a bad babysitter, the kind who lets the kids watch whatever they want on TV ’til way past bedtime, takes a long, luxurious bubble bath instead of watching them, and walks around the house in a bathrobe.
19. Lisa Bonet, The Cosby Show (1984-1991)
Lisa Bonet thinks she can do so many things—go to college, make Theo a knock-off designer shirt, star in a successful spin-off—but she fails at everything. She ends up dropping out of Hillman, sending Theo out in a shirt with an askew collar and one long sleeve, and returning to The Cosby Show with Raven Symone in tow after leaving A Different World. So it should come as no surprise to anyone who has seen The Cosby Show, or anyone who has seen a sitcom, that when Bonet criticizes her older sister (Sabrina Le Beauf) for relying on videotapes and processed foods for their infant twins, and says she can do better, that she’ll fail in spectacular, slapsticky ways. Bonet is a terrible babysitter. She can’t control the twins, who run all over the apartment knocking over potted plants and coloring in coffee-table books, so she resorts to plopping them down in front of a videotape. Unfortunately, the power goes out, the twins won’t stop crying, and Bonet forgets what food they’re allergic to, so she has to admit defeat and call her mother. But the incompetence doesn’t end there, because when the power comes back on, all the blenders and food processors she was apparently running simultaneously (sans lids) to make dinner for the twins snap back into action, spraying food all over the apartment. Yet another failure for Bonet.
20. Amy Sedaris, Strangers With Candy (1999)
When Amy Sedaris’ 48-year-old high-school freshman Jerri Blank first gets the job of taking care of a live infant in the episode “A Burden’s Burden”—a twist on the old home-economics standard where students have to tote around an egg for a week—she’s pretty excited. After all, she’s had plenty of babies (just none that she kept), and she knows that they don’t cost money, they make money, especially if their eyes stay blue. But when the baby she names Dizzy proves to be too much of a burden and won’t even respond to the shredded beer can she gives it to play with, her teacher partners her up with Tammi Littlenut. The episode then gets even freakier, with the two playing out a creepily funny variant on an abusive relationship and Jerri looking to farm out Dizzy to the black market so she can kick-start her sex life.
21. Billie Whitelaw, The Omen (1976)
It’s hard raising kids these days—with mom and dad both forced to work full-time, and the Internet and reality TV so readily available to impressionable minds, any loving parent must despair at finding a way to bring up Junior with most of his marbles still reasonably intact. Maybe hired help is the way, but as the original Omen showed, it pays to be careful about the help one hires, especially if one’s progeny just happens to have been adopted under mysterious, extremely suspicious circumstances. Billie Whitelaw seems like the perfect professional: she’s prim and proper, and she even comes with her own trained attack dog. But as Gregory Peck and Lee Remick eventually discover, she has some very peculiar ideas as to what’s best for their young son, Damien. Her unconventional nannying includes encouraging him to develop his demonic powers, assaulting his parents when they stand in her way, and, presumably, making sure the potential antichrist doesn’t develop anything remotely resembling a conscience.
22. “Molotov Cocktease,” Venture Bros. (2006)
On the surface, Molotov Cocktease seems like the dream babysitter of any straight guy or gay girl between the ages of 12 and whatever. A hot redhead in a skin-tight black uniform that just barely covers her considerable cleavage, she’s pure fantasy fulfillment, except for her explosive temper and her distressing yen for beating up anyone she’s attracted to. But Hank and Dean Venture have never been normal, and when, in the season-two episode “Assassinanny 911,” their usual bodyguard Brock Samson has to go on an adventure of his own, Molotov is charged with taking care of things in his absence. In addition to the perpetually deluded Venture boys, Molotov also has to deal with Hank and Dean’s father Rusty, the most ill-advised Casanova this side of George Costanza. When Hank falls for Molotov, it’s bad enough, but when he also sees his dad putting his moves on the supremely uninterested assassin, it’s the sort of Freudian nightmare that the Venture Bros. does best. Everybody manages to survive until the end, but things would’ve gone a lot smoother if Brock hadn’t added his would-be girlfriend to an already unstable household.