Bad parenting has been the go-to fuel for many movies over the years, especially when used to generate laughs in babysitter comedies. This weekend a pre-slimmed down Jonah Hill stars as a suspended college student that takes on a babysitting gig in The Sitter even though he is woefully unqualified. It's a good thing for black comedies that parents don't check up on the person who will be watching their little angels or we wouldn't get to see Hill take the kids to a party, grapple with unhinged drug dealers and tear through New York City with the tots on a wild ride.
Elisabeth Shue also drags the children she is babysitting along for a reckless romp around Chicago in 1987's Adventures in Babysitting, during which the 17-year-old sitter gets stranded on an expressway, detained at a chop shop and caught in the middle of a gang fight. With sitters like Shue on the loose, you're almost better off leaving your kids under the supervision of a sock puppet and a lengthy kiddie flick in the DVD player. The same applies to Brittany Murphy in Uptown Girls, who plays the rich daughter of a deceased famous guitar god who loses her inheritance and is forced to—what else?—babysit Dakota Fanning for cash, which of course leads to disaster.
In 1991's Don't Tell Mom the Babysitter's Dead, Christina Applegate and her four siblings are left in the care of a tyrannical elderly babysitter while mom skips town for a two-month sabbatical in Australia. When said babysitter croaks on the job, Applegate—the eldest daughter—takes control of the household and uses the opportunity to fake a résumé and elbow her way into a job in the fashion industry. Her double life soon catches up with her as being a 17-year-old working mom puts a serious damper on her dating life.
In the annals of babysitter comedies, there is ample evidence that Hollywood thinks men taking care of babies is a knee-slapping premise because, you know, it is not their traditional gender role. Get it? In Daddy Day Care, Eddie Murphy plays a laid-off father who turns his home into a daycare facility that the neighbors immediately suspect is run by perverts because why else would men want to be around children? In the John Hughes movie Uncle Buck, John Candy plays the titular character—a boozing, smoking gambling man—who helps his brother and sister-in-law with the kids after a medical emergency. Three bachelors get roped into taking care of one's love child in Three Men and a Baby, which became the biggest box-office hit of 1987. Fast forward to 2005 and The Pacifier, in which Vin Diesel—in his first non-action role—plays a Navy SEAL who is assigned to watch after five children in a Maryland house where a secret project is hidden.
Apparently the only thing sillier—and more profitable at the box office—than a man taking care of children is a man in drag taking care of children. In 1993's Mrs. Doubtfire, Robin Williams plays a divorced voice actor who must find gainful employment within three months to get more visitation rights with his kids. He adopts the persona of 60-year-old Scottish caretaker Euphegenia Doubtfire and applies for a nanny job at his ex-wife's house so he can be around his children every day. The children just adore their daddy in drag, but when Mrs. Doubtfire's true identity is exposed (Dad?!) mom (Sally Field) is forced to consider that, in an insane world full of terrible child caregivers, maybe your ex-husband dressed up as a benevolent old babysitter is the sanest choice if the wee ones behave.