That girl was a teenage tabloid queen.

Photo: Monika Fellner/Getty Images

Lindsay Lohan will always be synonymous with the early 2000s, Y2K fashion, and masterpiece movies filled with lines like “On October 3rd, he asked me what day it was. ‘It’s October 3rd.’” 

But society didn’t just only see the actress transition from the little girl in The Parent Trap to the young woman they saw in Mean Girls on the big screen. Instead, society also got to see Lohan’s personal life unfold on the front covers of tabloids plastered on newsstands everywhere.

Want to take a step back in time to hot pink and low-rise everything? L’OFFICIEL breaks down some of Lohan’s most iconic tabloid scandals.

1998

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While Lohan has been featured in a multitude of films over the years, her breakout role came in 1998, with The Parent Trap. Playing both twins— Hallie Parker, who grew up with her dad in California, and Annie James, the London-based twin who lived with her mother—Lohan was thrust into the spotlight at the ripe age of 11.

Early 2000s

‘Mean Girls’

During this time period, Lohan continued to work as a child actress. Starring in films like Life Size (2000), Get a Clue (2002), Freaky Friday (2003), Confessions of a Teenage Drama Queen (2004), and Mean Girls (2004), Lohan was still not a main character in the tabloids. However, she did find herself in an infamous teen star love triangle between herself, Hilary Duff, and Aaron Carter.

After Carter seemingly dated both girls around the same time, Duff showed up uninvited to the premiere of Freaky Friday in what many saw as retaliation for Lohan stealing her man. There were also rumors that Chad Michael Murray, who played Lohan and Duff’s love interests in their respective films Freaky Friday and A Cinderella Story, was dragged into the middle of the situation. Yikes.

2004

Photo: Frazer Harrison/Getty Images

In May of 2004, 17-year-old Lohan was romantically linked with That ’70s Show actor Wilmer Valderrama, who was 24 at the time. Presumably, given the fact that Lohan was still a minor, the two did not officially announce their relationship until she had turned 18 in July of that year, per People. But the two called it quits that same year in November.

2006

Photo: Getty Images.

2006 was the year that one of the most iconic tabloid photos of all time was taken. A photo with three 2000s icons—Lohan, Britney Spears, and Paris Hilton. Dubbed “The Holy Trinity,” the three sat in Hilton’s car after leaving the Beverly Hills Hotel. All cozied up in the car, the three looked like best friends, right?

Wrong. Years later, in 2021, Hilton actually said that, at the time, the two were not on the best of terms. Turns out, there had been rumors circulating that Hilton had just hit Lohan. However, when paparazzi comforted the two of them about it outside the hotel, Lohan denied the claims and ended up getting in the car with Hilton and Spears, according to E! News.

2007

In 2007, things took a turn for the worse. At the beginning of the year, Lohan entered rehab for the first time. By August of the same year, Lohan had been in rehab a total of three times, been arrested twice, and “she pleads guilty to misdemeanor cocaine use and driving under the influence,” per CNN.  And throughout this entire time period, various photos of Lohan’s mugshots and photos of her passed out in cars continued to circulate in tabloids.

2010

But Lohan did not complete the terms of her probation. And so, she was sentenced to 90 days in jail. After she served her time, she was also ordered to attend rehab again.

Only 24 at the time, Lohan had already been to rehab three times. As soon as she completed her fourth rehab visit though, she got in trouble again, when she failed a drug test. Soon after, she checked into rehab for the fifth time.

And in early 2011, she also was facing charges after stealing a $2,500 necklace, per E! News. 

2012

Photo: Valerie Macon/Getty Images

Lohan was arrested again twice in 2012—once after hitting someone with her car and driving away and again after an argument in a club, per CNN.

And according to The New York Times, in 2013, Lohan was ordered to attend rehab again, coming to a total of six rehab visits.

2013-present

Lohan has pretty much stayed out of trouble since then, with the exception of a weird incident that took place in 2018.

According to a Time article, in 2018, while live-streaming on Instagram from what appeared to be Moscow, Lohan approached two adults and two boys sitting outside. After claiming that were Syrian refugees and needed to be helped, she offered one child a place to stay and then criticized the mother for not working harder to take care of the children. She continued on to say that the mother was trafficking the kids. At one point, Lohan even put her hands on one of the children. The result? The mother supposedly punched Lohan. The Instagram video ended with Lohan in tears.

Otherwise, in 2014, she took part in an eight-episode docuseries. In 2019, she also had her own MTV reality tv show—Lindsay Lohan’s Beach Club— documenting the launch of her own club in Greece, per IMDb. She is also currently working on various projects like Lovestruck High, Falling for Christmas, and Cursed, according to IMDb.