From Cher to Selena Gomez: 10 Stars Who Babysat Fellow Celebs

From Cher to Selena Gomez: 10 Stars Who Babysat Fellow Celebs

Hollywood is full of surprising connections, and some of the most unexpected ones happened long before the red carpets and award shows.

Many celebrities got their start in the entertainment world by babysitting other famous kids who would later become stars themselves.

These stories reveal a fascinating web of relationships that stretches back decades, showing just how small the celebrity world really is.

1. Tia and Tamera Mowry Babysat Mary-Kate and Ashley Olsen

Back in the 1990s, two sets of famous twins crossed paths in the most ordinary way possible.

Tia and Tamera Mowry, already stars from their hit show Sister, Sister, spent half a day looking after Mary-Kate and Ashley Olsen, who were around 7 or 8 years old at the time.

Tamera shared this sweet memory in her 2022 memoir You Should Sit Down for This.

She remembered the Olsen twins as incredibly sweet girls who had a surprising favorite food: matzo ball soup.

The young actresses couldn’t get enough of it during their time together.

What stood out most to Tamera was feeling honored that the Olsens’ mother trusted them with her daughters.

Both sets of twins were navigating child stardom, making this connection even more special and relatable for everyone involved.

2. Selena Gomez Babysat Jessica Simpson’s Daughter Maxwell

When Maxwell Johnson was ready for her first-ever concert experience, her mom Jessica Simpson knew exactly who to call.

Selena Gomez stepped up as chaperone for the exciting night, accompanying Maxwell to see Olivia Rodrigo perform live.

Simpson couldn’t stop gushing about Gomez’s help during a 2022 Instagram Live session.

She publicly thanked the singer and actress for making Maxwell’s first concert such a memorable and special occasion.

Simpson specifically called out Gomez as “a great babysitter,” showing her appreciation for going above and beyond.

This friendship between the two pop stars clearly runs deep, with Simpson trusting Gomez to handle such an important milestone.

Maxwell got to enjoy her first concert with a superstar guide, creating memories that will last forever while her famous mom knew she was in excellent hands.

3. Nikki Glaser Babysat Maude and Iris Apatow

Before becoming a household name in comedy, Nikki Glaser had a pretty sweet gig watching over some future stars.

In 2007, she babysat Maude and Iris Apatow, daughters of comedy powerhouse Judd Apatow and actress Leslie Mann.

Speaking about the experience years later in 2026, Glaser joked that the $35 to $40 hourly rate was the most money she’d ever made at that point in her career.

The pay was clearly generous for babysitting work, reflecting the Apatow family’s appreciation for good childcare.

Glaser had nothing but praise for the girls, describing them as sweet and naturally funny.

Growing up in a comedy household clearly rubbed off on Maude and Iris, who both went on to pursue acting careers themselves, appearing in their father’s films and other projects.

4. Usher Babysat Beyoncé and Destiny’s Child

Long before Beyoncé became Queen Bey, she was just a young girl in a group called The Dolls, the early version of Destiny’s Child.

Usher, already rising in the music world, found himself responsible for watching over the future superstars during this formative time.

During a 2024 interview on the popular podcast Club Shay Shay, Usher opened up about this unexpected role.

While he downplayed being called a “babysitter,” he confirmed he was definitely responsible for looking after the group members early in their careers.

This connection shows how intertwined the music industry was in the 1990s, with young artists supporting each other before fame struck.

Usher got to witness Beyoncé’s talent firsthand, long before the world recognized her as one of the greatest performers of all time.

5. Cher Babysat Anthony Kiedis

The 1970s music scene was a tight-knit community where celebrities often crossed paths in unexpected ways.

One of the most surprising babysitting stories comes from Red Hot Chili Peppers frontman Anthony Kiedis, who revealed an unusual childhood memory in his autobiography Scar Tissue.

According to Kiedis, the legendary singer and actress Cher once babysat him when he was a teenager.

This fascinating detail highlights just how deeply intertwined celebrity circles were during that era, with musicians, actors, and artists all mingling together regularly.

Imagine having Cher as your babysitter!

The future rock star probably had no idea he was being watched by someone who would become an icon herself.

This connection shows the wild, creative environment Kiedis grew up in, which likely influenced his own artistic journey.

6. Donald Sutherland Babysat Gwyneth Paltrow

Oscar-winning actor Donald Sutherland had an interesting side job during his theater days.

When Gwyneth Paltrow’s mother, Blythe Danner, was working at the prestigious Williamstown Theatre Festival, she needed someone trustworthy to watch her young daughter.

Sutherland stepped up to the task, becoming young Gwyneth’s babysitter during that summer theater season.

Years later, after both had achieved major Hollywood success, Paltrow shared this charming story, revealing the accomplished actor’s lesser-known role in her childhood.

The Williamstown Theatre Festival connection makes sense, as it brought together talented performers from across the entertainment industry.

Sutherland’s willingness to help a fellow actor shows the supportive community that existed among theater professionals.

Paltrow grew up surrounded by incredible talent, which undoubtedly shaped her own award-winning career.

7. Alice Cooper Babysat Keanu Reeves

Shock rock legend Alice Cooper and Hollywood heartthrob Keanu Reeves seem like an unlikely pair, but they share a surprising connection.

Reeves’ mother worked as a costume designer and met Cooper through her work in the music industry.

This professional relationship led to Cooper taking on caretaker duties for the future Matrix star when Reeves was just a child.

Long before Keanu became one of Hollywood’s most beloved actors, he was being looked after by the theatrical rock performer known for his wild stage shows.

Cooper’s gentle off-stage personality contrasts sharply with his dramatic rock persona, making him a fitting choice for childcare.

Reeves has grown into one of the nicest people in Hollywood, and perhaps Cooper’s influence played a small part.

This connection proves that rock stars can be responsible babysitters too!

8. Bethenny Frankel Babysat Paris and Nicky Hilton

Before Real Housewives fame and building a business empire, Bethenny Frankel had a very different job.

She worked as Kathy Hilton’s personal assistant, a role that came with various responsibilities including childcare for the Hilton daughters.

Frankel’s duties included taking young Paris and Nicky Hilton to and from school during their younger years.

She got an up-close look at the glamorous Hilton lifestyle long before either she or the Hilton sisters became household names through reality television.

This early connection to the famous family gave Frankel insider knowledge of wealthy lifestyles, which later informed her own brand and business ventures.

Paris went on to become a reality TV pioneer herself, while Frankel built her Skinnygirl empire.

All three women ended up dominating pop culture in their own unique ways.

9. Michael Bolton Babysat Paula Abdul

Two future pop icons connected long before either topped the music charts.

Paula Abdul has shared stories about how singer Michael Bolton watched her when she was just a child, creating an unlikely early bond between them.

Bolton, who later became famous for his powerful ballads and romantic hits, was likely just starting his own music journey when he took on babysitting duties.

Abdul, who would go on to become a choreographer, singer, and television personality, was simply a kid at the time.

This connection shows how small the entertainment world can be, even before people become famous.

Both went on to achieve massive success in the 1980s and 1990s, with Bolton selling millions of albums and Abdul dominating both the music and dance worlds.

Their early friendship remains a fun footnote in both their careers.

10. Chloë Sevigny Babysat Topher Grace

Growing up in Connecticut, That ’70s Show star Topher Grace had a babysitter who would later become an indie film darling.

Chloë Sevigny, years before her breakthrough roles in independent cinema, worked as Grace’s nanny during his childhood.

At the time, neither had any idea they would both end up as recognizable Hollywood names.

Sevigny was just a local teenager earning money through childcare, while Grace was simply a kid who needed supervision after school and during evenings.

This suburban Connecticut connection seems worlds away from the glitzy entertainment industry both would eventually join.

Sevigny became known for her edgy, artistic film choices, while Grace achieved mainstream success on television and in movies.

Their paths diverged dramatically, but they share this charming early connection from their pre-fame days.