The Tragic Real-Life Story Of Lindsay Lohan

It seems unthinkable now, but back in the early 2000s, and thanks to roles in "The Parent Trap," "Freaky Friday," and "Mean Girls," Lindsay Lohan was known simply for her acting talents and not her ability to cause pure, unadulterated chaos wherever she went.

Of course, by the end of the same decade, the one-time Disney favorite had completely destroyed her reputation, with numerous run-ins with the law, displays of unprofessional conduct, and stints in rehab proving that she'd well and truly succumbed to the child star curse.

Some of Lohan's downfall was entirely of her own making, for sure, but there have undoubtedly also been other contributing factors outside of the star's jurisdiction. From troubling parental relationships and paparazzi stalking to infamous robberies and car accidents, here's a look at 14 of the most tragic moments from the tabloid regular's highly eventful life.

Ever wondered how the paparazzi always seemed to know exactly what Lindsay Lohan was up to during her wild child days? Well, according to the "Freaky Friday" star, they were repeatedly tipped off by a family member.

Yes, Lohan's difficult relationship with her dad, Michael Lohan, took another turn in the 2000s when she accused him of selling stories about her to the press. In an interview with Gossip Cop, the actor said (via Today), "I hate him so much. My father knows nothing other than how to sell stories for money instead of getting a real job like normal people do, including myself."

By this point, reports had already emerged that Lohan had finally cut her father out of her life, and a year later, she tweeted (via Express), "I don't want my ex-father anywhere near me no matter where I am. He is crazy and scares me." There was even talk of the actor filing a restraining order against him in 2012. However, the hostility between the pair appeared to thaw over the years, and in 2023, they were both pictured enjoying each other's company at a family gathering.

In 2016, concerning footage of a physical altercation between Lindsay Lohan and then-fiancé Egor Tarabasov during a getaway to the Greek Island of Mykonos surfaced online. This appeared to give the former child star the impetus to further open up about the reportedly abusive nature of their relationship.

Speaking about her romance with the Russian playboy, Lohan told the Daily Mail, "I realize now you can't stay in a relationship just for love. No woman can be hit and stay with that person if that person isn't prepared to say sorry." The "Herbie: Fully Loaded" star then claimed that the public spat wasn't the first time that Tarabasov had acted in such a manner.

Referring to a dispute that prompted neighbors to call the police several weeks earlier, Lohan said, "When we got home I went to bed and Egor went out. A few hours later he came back and when I woke up he was standing over me. He wasn't himself, he was being very aggressive and he attacked me ... I've kept quiet for so long but now I'm scared of what Egor might do to me and to himself."

In 2014, the most intimate details of Lindsay Lohan's private life went public when a list of her sexual history somehow found its way to the press. And every tabloid editor's dream came true when many of the 35 names featured were also celebrities.

Justin Timberlake, Colin Farrell, Evan Peters, Joaquin Phoenix, and Adam Levine were just a handful of the famous faces referenced on the list, something which Lohan had compiled as part of her recovery from addiction. During an appearance on "Watch What Happens Live," the "I Know Who Killed Me" star laid the blame for its leaking at an opportunist who'd taken a photo while she was in the middle of a house move.

"You know what, I'm going to get serious for a second," Lohan told host Andy Cohen. "That was actually my fifth step in AA at Betty Ford. And someone, when I was moving during the OWN show, must have taken a photo of it. So that's a really personal thing, and it's really unfortunate."

In 2007, a 21-year-old Lindsay Lohan checked herself into a Los Angeles rehab facility following an arrest for drinking under the influence. Of course, this would be just the first of many stints over the next six years.

In fact, that very same year, Lohan repeatedly returned to rehab, firstly completing 45 days in a Malibu treatment program after falling foul of the law for similar reasons and then heading to a Utah facility after she was charged with possession of cocaine. In 2010, the "Georgia Rule" star was ordered to spend time at the Ronald Reagan UCLA Medical Center, while a few months later, she checked herself into the famous Betty Ford Clinic for substance abuse issues. And there were several other spells in and out of rehab in between all these periods, too. 

In 2012, Lohan explained to Event magazine (via Today) why the rehab life isn't for her: "I don't think I need to be on lockdown for three months. I don't think that's rehab. Constantly sending me to rehab is pointless. The first few times I was court-ordered to rehab it was like a joke, like killing time. I think there are other things I could do instead of going to a rehab center that would benefit me more."

In 2015, Lindsay Lohan became the new face of car insurance company Esurance, a rather ironic turn of events considering the "Falling for Christmas" star has been involved in multiple vehicular collisions over the years (some not her fault, others very much so). 

Her first came in 2004 when she was allegedly responsible for a head-on collision, which she then drove away from. A year later, she was accused of plowing into a paparazzi photographer, Galo Cesar Ramirez's car, while trying to escape his cameras. However, on this occasion, she was seen as the victim, with the incident inspiring then-Governor of California, Arnold Schwarzenegger, to introduce a new anti-paparazzi law.

Lohan's road troubles continued later that year when she once again ended up causing an accident while trying to flee the tabloids. Her most serious occurred in 2012, though, when she rear-ended her Porsche into a dump truck during a drive on the Pacific Coast Highway. Luckily, no one was seriously hurt, but the actor got into trouble by wrongly insisting that her assistant, Gavin Doyle, had been behind the wheel.

The most heartbreaking of the many revelations Lindsay Lohan revealed about herself on the OWN network reality show was undoubtedly the fact that she'd suffered a miscarriage during its shooting. The "Chapter 27" star told viewers of the "Lindsay" season finale that this was the reason why she had to take two weeks off from work, adding (via the Independent), "It's a long story."

Lohan didn't go into much detail about this long story, but she did explain how she felt at the time: "I couldn't move, I was sick. Mentally, that messes with you." The actor also commented on how watching earlier episodes of the series filmed around this time made her feel uncomfortable: "There was a lot going on in my life then. I cried so many times watching it, because I don't see it as me ... it's strange. It's weird."

Nine years later, Lohan became a mother for the first time with the birth of Luai, the son she shares with financier husband Bader Shammas. "The family is over the moon in love," a spokesperson for the couple announced to People soon after.

Just like fellow former child star Britney Spears, Lindsay Lohan became a national punching bag once her troubled personal life started to overshadow her career. And perhaps surprisingly, legendary talk show host David Letterman was accused of sticking the knife in further than anyone else.

During a 2013 appearance on the "Late Show with David Letterman" to promote her role in "Scary Movie 5," a clearly uncomfortable Lohan was shown being grilled by the unforgiving host over a topic she hadn't beforehand agreed to. Questions included, "Aren't you supposed to be in rehab now?" "How many times have you been in rehab?" and "Do you have addiction problems?"

If that wasn't bad enough, the studio audience appears to find this interrogation extremely funny, perhaps spurring Letterman on to bring out a list detailing various things Lohan "has endured" over the years. "You can't make a joke of it," she pleads after snatching it and reading the contents for herself. "That's so mean." The clip went viral again eight years later when it resurfaced in the documentary "Framing Britney Spears."