How 2000s party girls Lindsay Lohan, Paris Hilton and Britney Spears grew up

Splashed across the front page of the November 29, 2006 front page of The New York Post was an image that encapsulated the mid-2000s in celebrity culture.

Three of the most famous women of that time — Lindsay Lohan, Britney Spears and Paris Hilton — were squished in the front seats of a car, Lohan snuggled into Spears’ lap.

All three were part of the posse of party girls who lit up the Los Angeles nightclub scene, and all three would have precipitous falls, all played out in public, before making their comebacks. Lohan is this week releasing Freakier Friday, the loudest declaration yet she is ready to reclaim the screen career that slipped away.

When that 2006 photo was taken, former friends Lohan and Hilton had been feuding for months, kicked off when Hilton was filmed giggling while her friend, oil heir Brandon Davis, sledged Lohan for, among other things, being “poor” because she was only worth $7 million.

Lohan gave back, once calling Hilton the C-word, and made a not-very-veiled jab about the hotel heiress’s 2003 sex tape.

As they left Guy’s Bar that night, all smiles and youthful insouciance, it seemed like the friendship was back on, although Hilton would in 2018 tell Andy Cohen that Lohan had actually gatecrashed the outing by chasing her and Spears to their car and squeezing in without an invite.

“I didn’t want to humiliate her in front of all the paparazzi and be like, ‘Get out of my car’ so it was like, whatever,” Hilton said.

The convergence event also captured that specific era when young Hollywood was known for having a good time as much as they were for their real jobs. Lohan, Hilton and Spears were in the thick of it, but that circle also included Nicole Richie, Hilary Duff, Mischa Barton, and The Hills’ Lauren Conrad and Heidi Montag.

They were rich, hot, privileged and perfect fodder for the explosion of celebrity gossip. Perez Hilton had launched in 2004 and TMZ the year after, and along with traditional tabloid sheets, at least one of these women could be relied on to stumble out of a club almost every night.

In 2005, Richie wrote in her biography, “The nightclubs of LA are like soap operas. There’s always some bizarre drama that plays out every single night, and everyone in the cast – I mean, everyone – is great looking.”

The antics were more salacious than anything that was playing out on The Hills or The OC or Confessions of a Teenage Drama Queen.

Bookended by the post-9/11 days and the start of the GFC, it was a vicious cycle in which fame and notoriety could be yours if you were papped outside the right club.

Social media was still an infant and it was years before anyone with half a profile could build their brand with curated posts, connecting directly to would-be fans without the intermediary of a media you can’t control.

You also have to remember how young they all were at the time. When that photo was taken, Hilton was 25, Spears was 24 and Lohan was only 20.

That New York Post spread had shamed all three by declaring their least favourite accessory was underwear, and listed each woman’s car accidents, DUIs and who they had feuded with.

It was a hard time to be a young woman in the spotlight when photo editors combed through photo sheets, looking for the least flattering picture.

Which is not to say that the practice has disappeared entirely. Some tabloid news websites still publish images of celebrities at their worst, sometimes under the disingenuous narrative of “fans are so concerned about X” but really they just want the clicks.

Within a year of that photo, Hilton had spent five days behind for violating a probation related to driving under the influence, Lohan went to rehab three times and jail once, and Spears had a public breakdown which led to a 13-year conservatorship.

Lohan became a cautionary tale for child stars, especially as anyone reading the magazines or clicking on those stories could shake their head and go, “What a shame, she was so cute in The Parent Trap”, while overlooking their own complicity in fuelling the tabloid machinery.

How fast Lohan fell mirrored how quickly she rose. After The Parent Trap, Lohan made a few TV movies (including Life-Size with Tyra Banks), but it was Freaky Friday and Mean Girls that supercharged her profile.

Other films including Confessions of a Teenage Drama Queen, Herbie: Fully Loaded and Just My Luck weren’t as successful but she was everywhere. In the four years to 2006, she released eight movies, and she only just turned 20 by the end of that run.

After that, her resume thinned and the projects became increasingly C-list, as Lohan’s personal life became risky for any major studio to take on. Between 2007 and 2013, she had her mugshot taken six times, for drink driving, cocaine possession, violating probation and reckless driving.

The year after, she left Los Angeles, uprooting to New York and London, and then eventually to Dubai, where she has lived for a decade. She has credited the move with giving her space to breathe, and added that paparazzi are not legal there.

She married her financier husband, Bader Shammas, in 2022 and a year later, gave birth to their son. While filming Freakier Friday, she would rush home as soon as her scenes were done to be with him.

Freakier Friday is a full circle moment for Lohan, 39, who shot the 2003 film when she was 15 years old, before all the headlines. She told Flaunt last year, “Being back on the lot emphasised to me that I made the right decision to take the time away to really soul search, find out who I am, what I love, what I want out of life, and how I want to live my future.”

Spears, 43, has had a more tumultuous time, all of it dramatically documented and culminating in the culture-shifting case in which she was finally freed in 2021 from the conservatorship her father held over her, controlling all her legal and bodily decisions.

She released a memoir – Michelle Williams narrated the audiobook – from a $US15 million book deal, and went through another marriage and divorce.

Charli XCX confirmed last year that she had been asked to write songs for Spears, but didn’t know if they were ultimately recorded.

Hilton floated around in the reality TV world (The World According to Paris), in music (singing and DJ-ing, and has charged up to $1 million for an appearance), in fashion and as a brand ambassador for the likes of Marc Jacobs, Skims and Uber Eats, but has more recently shifted to advocacy.

In the 2020 documentary This is Paris, she revealed she experienced emotional, physical and verbal abuse during her childhood and adolescence as a student at a series of boarding schools. She has testified in front of the US Congress three times about child abuse and threw her weight behind government legislation on the issue.

Like many celebs in the 2020s, she also has a podcast and a cooking show. Sure, everyone is a lifestyle influencer, but Hilton was one of the OGs.

As for the feud with Lohan, she told Watch What Happens Live in 2022, “I just feel like we’re grown-ups now. I just got married. She just got engaged. We’re not in high school. I think it was just very immature and now everything is all good.”

Most of the party girls grew up, even had kids of their own. Richie has the lifestyle brand House of Harlow, released a comedy rap album, and had an acclaimed run as a regular on the Tina Fey-produced sitcom Great News. Barton had a 32-episode guest role on Neighbours.

There are no new mugshots to be published.

When promoting her third Netflix movie, Our Little Secret, last year, Lohan told Flaunt, “I feel a huge sense of gratitude just to have lived through so many different experiences in life.

“I really have seen it all. Also, it’s made me so much stronger. It’s made me such a strong woman. I feel I’ve empowered myself in a lot of ways and that feels great. I know myself now at this age, better than ever.”