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.

It could be said that Lindsay Lohan's turbulent family life began at the age of four when her father was jailed for insider trading. Michael Lohan served three years in a Nassau County prison, the first of multiple legal issues the former Wall Street trader faced over the next three decades.

And things didn't get much better when Michael returned to the family home. In 2005, Lindsay appeared to imply that her father had been abusive to her mother, Dina Lohan, when she directed a music promo for "Confessions of a Broken Heart (Daughter to Father)" featuring lookalikes of both parents. "It was really to let girls, boys, anyone that's in an abusive relationship, anyone who is going through things like that ... to put it out there that it's OK to express how you feel," she later told Allure (via The Sydney Morning Herald).

Eight years later, Lindsay spoke more explicitly after shooting a scene in "The Canyons" in which her character tearfully responded to being assaulted by her boyfriend. "I've got a lot of experience with that from my dad," the actor later revealed to The New York Times.

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 a revealing 2006 interview with Vanity Fair, Lindsay Lohan revealed that she'd struggled with the eating disorder known as bulimia nervosa. And an appearance on America's favorite late-night comedy institution helped her to recognize that she had a serious problem.

"I saw that 'Saturday Night Live' after I did it," Lohan said (via Today), referring to her hosting stint on the NBC hit the year previously. "I had no arms. My arms were disgusting." The "Confessions of a Teenage Drama Queen" star then explained how dangerous the situation got. "I was making myself sick. I was sick and I had people sit me down and say, 'You're going to die if you don't take care of yourself.'"

Lohan's weight became an issue again three years later when she was pictured looking gaunt in the wake of her split from DJ Samantha Ronson. However, the former child star insisted on this occasion that nothing was wrong. "I like the way I look," she said (via Mirror). "I'm not starving myself, contrary to popular belief. I'm criticized when I'm too heavy or too thin."

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."

Lindsay Lohan was left grieving in 2019 when former boyfriend Harry Morton was discovered dead at his home in Beverly Hills. "Best friends. Best life," the "Mean Girls" star captioned an Instagram picture (via the Daily Mail) of the pair taken during their brief stint together 13 years earlier. "So sorry my lil princess, he's always with you, watching over you baby," her mother, Dina Lohan, then responded in the comments section.

Hard Rock Cafe heir Morton, who'd also been linked romantically to the likes of Britney Spears, Paris Hilton, and Demi Moore over the years, and Lohan became the It couple of the summer of 2006. They were spotted looking loved-up at a birthday bash for David Spade, at a Los Angeles party staged by Prada, and at various points during the Fourth of July week.

According to an insider, they split up after several months due to Lohan's penchant for drama. "It wasn't the partying that broke them up," they told People. "Harry's more low-key and not into the same stuff she's into." An autopsy later revealed that Morton died of a sudden cardiac arrest following a coronary artery disease that had previously gone undiagnosed. Four years later, another of Lohan's ex-boyfriends, Aaron Carter, died aged just 34. "My heart goes out to his family and may he rest in peace," she told Entertainment Tonight following the news. 

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."

It didn't exactly come as a surprise to anyone, considering the litany of arrests, wild nights out, and stints in rehab that has been plastered over the tabloids over the previous decade. But in 2013, Lindsay Lohan confirmed once and for all that she had a substance addiction. And, of course, the individual who made her comfortable enough to come clean was Oprah Winfrey.

During an interview on "Oprah's Next Chapter," the legendary talk show host explicitly asked Lohan whether she was an addict. After answering in the affirmative, "The Parent Trap" star also revealed that alcohol was her main drug of choice, adding (via HuffPost), "That, in the past, was a gateway to other things for me ... I tried cocaine with alcohol."

Lohan had previously admitted to using cocaine a handful of times before. But she told Winfrey that the real number was in the double figures range. "I really haven't done it more than 10 to 15 times. Of course, I said three or four. I was terrified of being judged. [Cocaine] allowed me to drink more. I think that's why I did it when I did it. It was a party thing. I snorted it. I've never injected anything, except getting B-12 shots ... But yeah, it went hand in hand with drinking."

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."

After multiple arrests, charges, and court-ordered rehab stints, Lindsay Lohan was finally sentenced to jail in 2010 after violating her probation rules. The "Labor Pains" star spent less than two weeks at Lynwood Correctional Facility, but soon found herself facing more time. She was also sentenced to 120 days in 2011 after pleading no contest to both probation violation and misdemeanor theft. Luckily for the actor, the issue of overcrowding meant that she got to avoid going behind bars, instead serving her sentence with an ankle monitor under house confinement. 

Toward the end of that same year, Lohan returned to a jail cell when she was judged to have broken her probation terms once again. But instead of the 30 days initially imposed, the New Yorker only ended up spending five hours at California's Century Regional Detention Facility.

This appeared to be the wake-up call that Lohan needed; however, as she went on to fulfill all of her probation requirements, and apart from a minor involvement in a cryptocurrency scandal, she hasn't fallen foul of the law since. In a 2013 Daily Mail interview with Piers Morgan, the star said, "I believe things happen for a reason. I live without regrets. There are certain things I have done, mistakes that I made, that I would change, but I don't regret them at all, because I've learned from them."

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.

In 2011, Lindsay Lohan ended up in a jail cell situated right next to an individual named Alexis Neiers. In a coincidental turn of events, the latter was a member of the Bling Ring group responsible for stealing $130,000 worth of goods from the "Just My Luck" star's rental home.

Yes, in 2009, the gang of thieves, famous for robbing the houses of the rich and famous, decided to target their ultimate prize. Rachel Lee, Diana Tamayo, and Nick Prugo subsequently looted a stash of expensive jewelry and clothes from the Hollywood Hills property Lohan had been residing in for several months. But thanks to the actor's extensive surveillance cameras and a tip-off from Neiers, the trio were caught.

A spooked Lohan decided to move out of the home immediately after the robbery, which was famously portrayed four years later in Sofia Coppola's "The Bling Ring" and then in the HBO documentary "The Ringleader: The Case of the Bling Ring." Owner Jenna Gering told The Journal that despite her hastiness, the Hollywood veteran left the place in great condition, with the paparazzi camera-shaped holes in the surrounding hedges the only notable sign of damage.

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.

One of the most emotional scenes Lindsay Lohan has ever filmed appears in 2006's "Bobby" when her character Diane's friend is shot during the assassination of Senator Robert F. Kennedy. And the actor's believable performance came from a place of real-life turmoil, for she shot the scene the very same day that a close family friend lost her life to meningitis.

"Our families are best friends and she was like a cousin, so you can imagine," Lohan later told Interview (via MTV). "I was on the phone with her parents every single night, and just before she died, I wanted to fly back to see her so badly." Unfortunately, Lohan's commitments to Emilio Estevez's directorial effort prevented her from going to see the lady in question.

Discussing the aforementioned scene, Lohan added, "It was the most tragic one I've ever had to do and required the most acting. Other roles I've had didn't require as much acting, because my character was closer to my own age and experience. This time, I had to go to that darker place and use that for my work."

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."