From sitcoms to dramas, television has long had a fascination with the nanny and babysitter figure. Sometimes they’re quirky comedic relief, sometimes wise sages, and occasionally, they’re just along for the ride while chaos unfolds around them. As someone who has worked in childcare for nearly two decades — from nannying to sleep consulting and childcare coaching — I can tell you firsthand: these portrayals range from laughably off-base to surprisingly insightful.

So today, I’m diving into the top TV series that put nannies and babysitters in the spotlight. We’ll look at how these shows have shaped public perception of childcare providers, what they got right (and wrong), and how pop culture reflects broader societal views on family, class, and care work.

The Nanny (1993–1999)

Let’s start with the glammed-up queen of TV nannies — Fran Fine. The Nanny gave us fashion, fabulousness, and a wildly unconventional take on childcare. Fran Drescher’s portrayal of the flashy, nasal-voiced nanny from Queens who stumbles into high society might not reflect a typical hiring process (or resume), but she does represent something crucial: the heart and humor a great nanny brings to the job.

From a professional standpoint, no, The Nanny doesn’t dive into developmental milestones or emotional regulation strategies — but it does show something just as important: building deep emotional bonds with children.

Nanny Score: 7/10 Realism, 10/10 Icon Status

Jessie (2011–2015)

Disney Channel’s Jessie introduced a whole new generation to the idea of nannying. Jessie, a young aspiring actress, ends up caring for four wildly different kids in a luxury New York penthouse. While the setup is more fantasy than fact, the show deserves credit for highlighting the importance of consistent caregiving, patience, and problem-solving — all key tools in any real nanny’s kit.

Nanny Score: 5/10 Realism, 8/10 Heart

Charles in Charge (1984–1990)

One of the earlier shows to feature a male nanny-esque figure, Charles in Charge broke ground by challenging traditional gender roles in caregiving. Charles may have been a college student, but he was managing chaos, carpooling, and helping raise children — that’s peak nanny life right there.

Nanny Score: 6/10 Realism, 9/10 Groundbreaking Vibes

The Baby-Sitters Club (1990, 2020)

A gold standard in portraying young caregivers, both the original and reboot of The Baby-Sitters Club took babysitting seriously. The girls ran their work like a business and tackled real-world challenges — disabilities, grief, blended families — with compassion and maturity. As a career nanny, I love that this series shows how babysitting can be more than just a teen job — it can be a calling.

Nanny Score: 9/10 Realism, 10/10 Emotional Depth

Who’s the Boss? (1984–1992)

Tony Micelli, a former pro athlete turned housekeeper, showed that caregiving isn’t exclusive to women. While he technically wasn’t a nanny, he handled many of the responsibilities — nurturing, discipline, and emotional support — that nannies do every day. His role paved the way for more nuanced portrayals of male caregivers.

Nanny Score: 8/10 Realism, 8/10 Representation

The Haunting of Bly Manor (2020)

More ghost story than babysitter drama, but beneath the chilling exterior lies a deep meditation on grief, caregiving, and sacrifice. Dani’s relationship with the children under her care is tender, protective, and powerful. Though the horror element is front and center, the caregiving relationships are refreshingly real and emotionally grounded.

Nanny Score: 10/10 Emotional Authenticity, 6/10 Realism (unless you believe in ghosts)

Honorable Mentions: More Sitters & Nannies Who Left Their Mark

While they didn’t make the main list, these characters and shows deserve a shout-out for their contributions to pop culture’s portrayal of childcare:

Minding the Store (The Amanda Show)

Who didn’t grow up giggling at the absurd “babysitter” sketches on The Amanda Show? Sure, it was chaotic and exaggerated, but it showed just how central sitters are in kids’ imaginations — even if they’re occasionally weird or totally unqualified.

The Suite Life of Zack & Cody – Maddie Fitzpatrick

Maddie wasn’t a traditional nanny, but as a candy counter worker who often got wrangled into babysitting the twins (and London Tipton), she modeled that teens in childcare roles can balance discipline, fun, and affection.

Scandal – Olivia Pope’s “Nanny” Moments

Unlikely entry? Sure. But Olivia Pope stepped into more of a nanny/guardian role for Quinn and other “Gladiators” multiple times. Though it wasn’t literal childcare, the emotional labor she provided echoed many of the same instincts professional caregivers lean on — protection, loyalty, and fierce advocacy.

Gossip Girl – Dorota Kishlovsky

Dorota, Blair Waldorf’s devoted housekeeper and confidante, often felt more like a full-time nanny than anyone else on the Upper East Side. Her nurturing influence, discipline, and ability to manage tantrums (Blair’s, mostly) made her one of the most underrated TV caregivers of all time.

Two and a Half Men – Berta the Housekeeper

Berta wasn’t hired as a nanny, but she took on a major caregiver role with Jake, especially when Charlie and Alan couldn’t get their act together. Her blunt wisdom and no-nonsense attitude? Classic caregiver gold.

SNL’s Various “Babysitter” Sketches

From Kristen Wiig to Kate McKinnon, Saturday Night Live has done dozens of wild babysitter sketches — often exaggerating stereotypes, but also capturing the cultural expectation that sitters have to be miracle workers… with zero training and $10/hour.

Final Thoughts

Whether played for laughs, thrills, or heartfelt family moments, nannies and babysitters have shaped the way pop culture portrays caregiving. As someone who’s lived this work day in and day out, I see both the beauty and the fiction in these portrayals. While many shows focus on hijinks and heartwarming moments, real childcare work is layered, skilled, and deserving of greater recognition.

Still, I’m grateful these characters exist. They remind audiences — and maybe even future employers — that caregivers aren’t just background characters. We’re the calm in the chaos, the structure in the storm, and the heart in the household.

And who knows? Maybe one day we’ll get a series that shows the real day-to-day life of a career nanny — spit-up, spreadsheets, behavioral plans, snack negotiations, and all. When that day comes, I’ll be first in line to consult.

Until then, consider this your reminder that behind every great TV child… there’s probably a very tired, very loving nanny off-camera making it all happen.