Melissa Joan Hart Recalls Taking Britney Spears to Her First Club: 'I Feel Really Guilty' (Exclusive)

The actress sat down with ET for a new rETrospective and opened up about her career and friendship with the 'Toxic' singer.

Melissa Joan Hart says that, in retrospect, taking Britney Spears to her first-ever club was not the best way to be a sister and role model to the pop icon.

The 48-year-old actress recently sat down to do a rETrospective with ET and opened up about her decade-spanning career, her most iconic projects -- including Clarissa Explains It All and Sabrina the Teenage Witch -- and her friendship with Spears, 42, which began when she starred alongside her in the music video for "You Drive Me (Crazy)."

"Britney and I got to do a lot of press together. And we had a lot of fun together during this time," Hart shared while looking back on clips and photos of herself and the singer from 1999 and beyond. For the actress -- who is six years older than Spears -- she felt a sibling-style bond with the then-teen. 

"I saw that she was just surrounded by people, never able to break free. And I was like, 'Hey want to come?'" Hart shared of getting the GRAMMY Award winner to break out of her shell and go to a nightclub with friends. "I would go to a club every night -- I love dancing and I loved going out, but I also knew to be responsible and, like, when to stop."

Melissa Joan Hart and Britney Spears pose together - Getty

The "Womanizer" singer was 17 when the song and the wildly popular music video Hart appeared in was released. The track was from Spears' debut album, Baby One More Time, which came out just months before her 18th birthday.

The video -- which has more than 206 million views on Spears' YouTube channel -- also features The Devil Wears Prada actor and late 90s heartthrob Adrian Grenier, and follows Spears and Hart playing dress up with friends before partying and dancing in a warehouse-like setting. The song and music video accompanied Hart and Grenier's film, Drive Me Crazy, which released around the same time as Spears' album. 

Hart says that while she was young and didn't know better at the time, it's something she thinks about "to this day" as hindsight is 20/20. The "Oops!... I Did It Again" singer later struggled with partying in the early 2000s, but has also written about drinking with her mom at an early age in her 2023 memoir, The Woman in Me

"She was underage and young and -- but I [was] just like, 'Let's go out. We're just gonna go out and have some fun.' And yeah -- and I feel really guilty about that still to this day because I should have known better, being a big sister," Hart told ET. 

As fans well know, less than a decade after she first went out with Hart to a club, Spears would find herself in a highly contentious conservatorship with her father, Jamie Spears, who "temporarily" took over as she purportedly struggled with mental health issues. An Los Angeles court later made the conservatorship permanent, giving Jamie, 71, and another co-conservator power over her finances and medical decisions.

In November 2021, after 13 years and a passionate #FreeBritney movement, a judge terminated the conservatorship, granting Spears the freedom to control her career, finances and big life decisions, including the ability to get married or have a baby -- which she testified in September 2021 she was not allowed to do while under the conservatorship. 

Hart tells ET that she hasn't maintained constant contact with the singer and Crossroads star, but that she did get to see her while Spears was performing in her Las Vegas residency, Britney: Piece of Me

"I saw her when she was doing her Vegas residency a few years back, but she was doing her show so, you know, it was a quick hello backstage and that was it," Hart told ET of their most recent encounter. 

Britney Spears and Melissa Joan Hart - Getty

For the Melissa & Joey star, however, Britney's struggles and life story have forever impacted her, she says, including the decision to sign onto her new Lifetime film, The Bad Guardian. The upcoming film sees Hart star as Leigh, a woman desperately trying to get her father out of a toxic guardian situation. 

"When Leigh’s (Hart) father Jason (Eric Pierpoint) suffers a fall while she’s out of town, the courts assign Jason a guardian, Janet (La La Anthony). At first Janet seems to be a big help to Jason, but things quickly take a terrible turn. Janet is legally in charge of every aspect of Jason’s life, and doesn’t waste any time placing him in a nursing home, auctioning off his house, all worldly possessions, and using the excuse that the proceeds are needed for his care," a description for the film reads. 

Hart says she was inspired to tell the important story partially because of Spears and Wendy Williams -- who is currently under a guardianship -- and to keep the dialogue surrounding the difficult topic going. 

"It's kind of encompassing a lot of different stories. It's not one person's story, but this is happening all across the country where people are losing family members to guardianships, to these permanent guardianships that judges put in place to protect the person, usually seniors," she shared. 

"I mean, we know as Britney or Wendy Williams, having guardianships that are, you know, causing conflict. But in a lot of cases, it's families who lose a senior family member," she continued, emphasizing how difficult and costly the situations can be in real life. 

Hart continued, sharing that while some guardianships are necessary and beneficial for a person in need, there is a lot of duplicity in the business. In 2021, Rosamund Pike starred in a film from the side of a scrupulous, but malicious court-appointed guardian in Netflix's I Care A Lot, which earned the Saltburn actress a Golden Globe. 

"Once the doctors and the judges decide this person needs help, a guardian is put in place and a lot of times, it's not a family member. It's a $2.9 billion business," Hart said. "And while most of them are legit guardianships that people that need guardianships, there's a lot of corruption. And so we're kind of highlighting the corruption in this movie."

She told ET, "I'm really proud of it.. think it's a captivating movie and I'm -- I'm really happy that we could get the story out."

The Bad Guardian premieres on Lifetime on May 18.