Highlights

  • Lindsay Lohan and the Olsen Twins were known for their fame in the mid-2000s.
  • Lohan's relationship with DJ Samantha Ronson attracted immense media attention.
  • The iconic "It's Totally Raining Teens" Vanity Fair cover featuring Lohan, the Olsen Twins, and Hilary Duff was a high-stress experience.

Looking back at Lindsay Lohan and the Olsen Twins, it is obvious that the three women have a lot in common. During the mid-2000s, all three women were very famous and now they have completely changed their lives.

After Lohan moved to Dubai, she became a wife and mother who no longer is a mainstay of the tabloids. Similarly, the Olsen twins mostly avoid the spotlight as they work as fashion designers. Despite everything they have in common, Lohan reportedly feuded with Ashley Olsen over her ex-girlfriend Samantha Ronson.

Did Lindsay Lohan And Ashley Olsen Feud?

During the late-2000s, Ashley Olsen had already ended her acting career, but she was still making public appearances. Unfortunately for Lindsay Lohan, during the late-2000s she was involved in a myriad of controversies as she was hounded by the paparazzi. One of Lohan's romantic relationships from that era especially got a lot of attention.

According to Whos Dated Who, Lohan dated a DJ named Samantha Ronson for just over two years between 2007 and 2009. During the former couple's relationship, the tabloids often breathlessly reported on every rumor about Lohan and Ronson.

In many cases, Lohan and Ronson made it easy for the media to find a new story about them. Between sometimes trading barbs on social media, appearing at public events together, and more, the tabloids always seemed to have more material to report on.

Related: Lindsay Lohan's Nearly Unknown Brother Dakota Lohan Has A Completely Different Relationship With The Star Than The Rest Of Their Family

Even for a couple that was often labeled dramatic, Lohan and Ronson got into a shocking situation in April 2008. That month, there were reports that Lohan got into an explosive argument with Ashley Olsen that was focused on Ronson.

When Olsen was still a child, she starred in the extremely successful and family-friendly sitcom Full House. Based on how sticky sweet Olsen's childhood image was, the idea that she would get into late-night drama at a nightclub took most of her fans by surprise.

During Lohan and Ronson's relationship, it was often reported that the Mean Girls actor would attend her girlfriend's DJ gigs. In 2008, Lohan's decision to watch Ronson perform at New York's Beatrice Inn reportedly led to her argument with Olsen.

According to Page Six's reporting after the incident, Lohan had been frustrated with Ronson that night. The reason for that according to Page Six is that Lohan felt Ronson "was ignoring her".

With Lohan reportedly already on edge, it became a problem when Olsen greeted Ronson. "Ashley Olsen said hello to Sam at [the Beatrice Inn in New York City], and Lindsay screamed at her, 'Get your 15-year-old Full House a-- away from my girlfriend,'"

Related: Did Turning Down Fuller House Mean Mary-Kate And Ashley Olsen Missed Out On A Life-Changing Salary?

After Lohan reportedly screamed at Ashley Olsen that night, there weren't any reports about the women fighting after that. However, according to a US Magazine report, Lohan wound up having an incident with Mary-Kate Olsen.

In 2011, Lohan and Mary-Kate Olsen's shared love for fashion resulted in drama. At the end of New York's Fashion Week in 2011, Lohan and her friend attended a party thrown by V Magazine.

According to US Magazine, Lohan was seated at the same table as Mary-Kate Olsen and her friend Dakota Fanning. Whether it was related to Lohan's drama with Ashley Olsen or not, Mary-Kate Olsen reportedly was mad to be seated near the Mean Girls star.

After Mary-Kate Olsen asked to be seated somewhere else and was told that wasn't possible, she reportedly gave Lohan the side-eye. "She looked so upset about her seat and kept looking over at Lindsay."

It was also reported that Lohan ended up at the same event as Mary-Kate Olsen and Fanning the following night. According to US Magazine's report, Fanning was seen rolling her eyes at Lohan. Mary-Kate Olsen and Fanning also reportedly did what they could to keep their distance from Lohan at the second event.

What Did Hilary Duff Think Of Her Famous Photoshoot With Lindsay Lohan And The Olsen Twins?

In 2003, Vanity Fair published a magazine that had a cover that has gone down in Hollywood history. Emblazoned with the words "It's Totally Raining Teens", the cover photo featured a who's who of female teen stars from the era.

Related: Lindsay Lohan's Net Worth And Career Would've Changed Forever Had She Not Missed Out On Starring In Friday Night Lights

That famous photo featured The Olsen twins, Lindsay Lohan, and Hilary Duff. On top of that impressive foursome, Amanda Bynes, Alexis Bledel, Evan Rachel Wood, Mandy Moore, and Raven-Symoné all also appeared on the cover.

With such an impressive roster of actors on the cover, that issue of Vanity Fair garnered a lot of attention. In fact, the cover photo was so memorable that Hilary Duff was asked about being included almost twenty years later in 2022.

In 2022, Duff appeared in a video for Vanity Fair's YouTube channel. During that video, Duff took a lie detector test and was asked about the "It's Totally Raining Teens" photo. When Duff was asked if being part of the photo was a career-high, her response was very telling.

"Like explain career high? Like personal high or just like a big achievement? Like I remember being like, 'This is cool I was included in this.' But no, this was a very high-stress, anxiety-inducing day."

Years before Duff's video was released, Evan Rachel Wood tweeted about the "It's Totally Raining Teens" photoshoot. According to what Evan Rachel Wood wrote, the photoshoot was a miserable experience for the Westworld actor. “I was almost in tears after this shoot. They tried that dress on me. 'I wasn't comfortable but they told me there was no time."

Wood continued, "Everyone else took up too much time with their fittings, Then I was given a choice on whether I wanted to wear flats or heels. I chose flats and was immediately handed heels and told they looked better. I was 15 and felt for the first time my identity was being erased and the pressure to shut up and do what you are told."

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