She starred alongside Adrian Grenier in the teen romance, which was named for Spears’ single ‘(You Drive Me) Crazy’ that appeared on the soundtrack.

Hart and Grenier, 47, also appeared with Spears in the song’s music video, and the popstar made a cameo on Hart’s Nickelodeon show Sabrina that year.

Melissa Joan Hart admitted she feels ‘really guilty’ about taking Britney Spears to her first nightclub when she was underaged

The outing came years before Spears’ 2008 meltdown and subsequent conservatorship

‘I saw that she was just surrounded by people, never able to break free,’ she recalled. ‘And I was like, “Hey want to come?”

‘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,’ added Hart.

The Bad Guardian actress recounted of their first night out, ‘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.”

‘I feel really guilty about that still to this day because I should have known better, being a big sister,’ said Hart.

She previously detailed their first night out as she appeared on Bethenny Frankel‘s talk show in 2013, admitting she left Spears at the club.

‘So I went to her hotel and I invited her to come out with me and we went to a club,’ said Hart.

‘She was underage so I snuck her in the back door and we did a little dancing and then people sort of swarmed on top of her and then she got stuck at a table hanging out with people, chit chatting,’ she recalled.

Hart added. ‘And I was like, “I’ve got to go to work tomorrow can I go?” And she was like, “Yeah, yeah, yeah. No, go I am good. They will get me home.”‘

Spears was placed under conservatorship in 2008, lasting until 2021, when she gave testimony about ‘abusive’ treatment she allegedly suffered.

‘Britney and I got to do a lot of press together,’ Hart told ET of promoting 1999’s Drive Me Crazy. ‘And we had a lot of fun together during this time’

The Bad Guardian actress recounted of their first night out, ‘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”‘

‘I feel really guilty about that still to this day because I should have known better, being a big sister,’ said Hart

The Glory artist has recently sparked concerns of another mental health episode after sustaining an injury at the Chateau Marmont in Los Angeles.

She was doing cartwheels outside her hotel room when she twisted her ankle, following some drinks at the hotel bar with boyfriend Paul Soliz.

Spears said she was ‘harassed and gaslit and tricked to go on the street‘ barefoot to meet the ambulance.

‘I was in my pajamas and yes, I had been crying because I hurt my foot!!! No breakdown!!! I’m a grown a** woman who is actually very naïve in most situations!!!’ she wrote on Instagram.

A source previously told DailyMail.com that it was Britney’s mother Lynne who ‘called 911 and told them that Britney was having a breakdown and had injured herself,’ knowing that her daughter ‘was in a traumatized state.’

The Glory artist has recently sparked concerns of another mental health episode after sustaining an injury at the Chateau Marmont in Los Angeles

A source previously told DailyMail.com that it was Britney’s mother Lynne who ‘called 911 and told them that Britney was having a breakdown’

‘Britney was crying in pain and she called Lynne in Louisiana to tell her what had happened,’ the insider said. ‘At the time, Lynne was the only one who knew that she had hurt herself.’

Seeing a gurney was ‘traumatizing’ for Spears, triggering ‘a severe panic attack’ after she was placed under a 5150 involuntary psychiatric hold in 2008.

Spears has since reportedly threatened to sell her Kentwood, Louisiana mansion Serenity, where her mother has lived rent-free since it was built in 2001.