Oh, Lindsay Lohan, we miss our teen idol so much. LiLo was on top of the world in the late ’90s and early ’00s. After landing her breakthrough role as both Hallie and Annie in The Parent Trap, she went on to star in some of the most influential teen movies like Freaky Friday, Confessions Of A Teenage Drama Queen, and of course, Mean Girls.
But like most child stars, something went wrong along the way. When we think of LiLo, we think of her early days, but what has happened since then? Well, she’s basically been involved in scandal after scandal, and we have them all here for you. Read on to chart the rise, fall, and possible resurrection of Lindsay Lohan.
A Child Model For Big Names
Before The Parent Trap, LiLo was already making a name for herself in the fashion world. She signed onto the Ford Modelling agency when she was only 3. Her first gigs were modeling for brands like Abercrombie and Fitch Kids, and Calvin Klein Kids.
Her modeling success no doubt helped her land some of her first smaller roles of television and film.
Her Big Break
The Parent Trap skyrocketed Lindsay into stardom. After that, she could basically land any role she wanted. She was so squeaky clean that she turned down the role of Regina George in Mean Girls because she didn’t want to be that mean in front of her young fan base.
Oh LiLo, you have no idea how your young fan base would watch you change.
She Worked Her Way Into Singing
Just as she cemented her status as a teen idol, Lindsay decided to branch out from acting. She released her debut album Speak in 2004, which actually sold quite well.
Her second album, A Little More Personal (Raw), was released in 2005 and gave the public a glimpse at the personal problems in LiLo’s life.
While this only looked like a blip on the radar, Lindsay’s life would quickly take a turn for the worse.
A Family Torn Apart
One of the songs from her second album was titled "Confessions of a Broken Heart (Daughter to Father)" and was all about the pain her father, Michael Lohan, had put the family through.
Her parents Michael and Dina separated when Lindsay was only 3, later reunited, then divorced again in 2007. The family struggles would play a key part in LiLo’s personal struggles.
A Lohan Family Scandal
As if Lindsay’s dad hadn’t already done enough to tear apart her family, LiLo learned in 2012 that she has a secret half-sister.
Things get weirder though, because it came to light that her half-sister Ashley had undergone jaw, chin, and nose surgery to look more like her famous half-sister Lindsay.
A Slew Of Arrests
After her parent’s final separation, Lindsay spiraled out of control. Between 2007 and 2012, she was arrested a shocking 20 times for everything from DUIs to grand theft.
Her constant appearances in court made her a fixture in the daily tabloids, but not for being an acting or singing icon. The media attention made it even harder for her to follow the rules.
While Lindsay started to spiral, she would be found with some other high-profile celebs who were also notorious in Hollywood.
A High-Profile Conversion To Islam
In 2016, Lindsay announced on social media that she was in the process of converting to Islam. This came at the height of her activism for the Syrian refugee crisis.
She even publicly called out a security guard in London Gatwick Airport for "racial profiling" her and asking her to take off her headscarf.
LiLo Got Extra Personal On Her Reality Television Show
Lindsay took part in an 8-episode reality series about her life on the OWN Network. The show was pretty bland and mostly showcased Oprah giving LiLo advice after her release from rehab.
On the 8th episode though, Lindsay revealed she had a miscarriage while filming and that is why they cut the series short.
Dominating The Hollywood Party Scene
The Kardashians may own the clubs today, but back in 2007, Lindsay Lohan and Paris Hilton were the top dogs. To put it in context, back in 2007, Kim Kardashian was working as LiLo’s personal assistant. Oh, how times have changed.
Her partying antics were half the reason she had so many DUIs.
2007 would really kickstart the beginning of the end for Lindsay, but the weirdest thing happened when she went in for an emergency surgery.
She Was The Victim Of The Bling Ring
The Bling Ring was the notorious Hollywood crime ring made up of teenagers who burgled the homes of many high profile celebrities. According to the ringleader, Rachel Lee, LiLo was her "ultimate fashion icon" and the heist would be the "biggest conquest."
They stole nearly $130,000 worth of clothes and jewelry.
She Used To Hate Alcohol
Despite being a central part of the Hollywood party scene and being arrested for multiple DUIs, LiLo used to hate alcohol. She never actually had a sip of any until she was 17, and when she did, it made her really sick.
Her mom taught her a lesson by making her sleep in the dried up vomit on her clothes. Unfortunately for her, that hatred of alcohol didn’t last long.
She Had Her Appendix Removed…And Kept It
In 2007, Lindsay had an emergency appendectomy to get her appendix removed and she insisted the doctors let her take it home with her.
This happened at the start of her downhill spiral, and Lindsay feared crazy fans would try to sell her appendix online or on the black market. Apparently, she kept it in her fridge for weeks.
Lindsay’s love life seems to constantly make its way into the limelight, but what does she think about it all?
The Mysterious Appearance Of A Strange New Accent
The media started buzzing again back in 2017 when Lindsay started doing interviews with a strange new accent. It sounds somewhat Mediterranean with a little bit of Arabic.
She claimed it was her way of learning different languages like Arabic and Greek, but people thought it sounded more like she was trying to fit into a culture.
Heath Ledger Gave Lindsay Important Advice Right Before He Died
Not long before Heath died tragically in 2008, he told LiLo to give up drinking. Apparently, he’d also just given up drinking for a year and it changed his life dramatically.
The two apparently had an extremely close bond, and diary entries showed that Lindsay was "in love" with him around the time of his death.
Even She Doesn’t Know Her Sexual Orientation
Lindsay has dated some of the biggest names in Hollywood from Aaron Carter to Wilmer Valderrama. She also dated DJ Samantha Ronson for more than a year.
When asked if she considered herself a lesbian or bisexual, she said “Maybe. yes. I don’t want to classify myself.” Following up in 2013, she said it was still unknown to her and that she was just looking for something different.
While we know she’s been arrested multiple times, what she did in court sent shockwaves through the tabloids.
Speaking Of Dating, She Kept A Pretty Interesting List
Lindsay made headlines yet again for her sex life when a list of every person she’s ever had sexual relations with was leaked to the paparazzi.
The list of over 30 names was apparently made in rehab and includes basically anyone you could think of, like Justin Timberlake, Heath Ledger, Zac Efron, and Ashton Kutcher, just to name a few.
In And Out Of Rehab
The party scene introduced LiLo to some dangerous substances. In an interview with Oprah, she admitted to doing cocaine “10-15 times” because it allowed her to drink more. She has admitted herself to numerous rehab facilities.
That, along with her longstanding legal issues, means LiLo has spent 87% of her life either in rehab or on legal probation.
Lying To A Judge’s Face
In 2011, Lindsay was sent to court over the theft of a $2,500 necklace. The judge sentenced her to court-ordered therapy sessions and LiLo said she couldn’t do it because she couldn’t afford it. Hey, we all have money troubles, but Lindsay said this while wearing a $1,200 pair of Christian Louboutins.
The judge wasn’t happy, and the statement made the public question her completely.
She’s Spent Time In Jail With The Girl Who Robbed Her
If you add up all the time LiLo was sentenced to jail for her various crimes, she was set to serve 391 days in a cell. At the end of it all, she spent only two weeks in jail.
Remember the Bling Ring that robbed LiLo’s home though? One of the girls, Alexis Neier, had a cell right next to Lindsay. We would pay to have heard the conversations they had.
She’s At Peace With Her Past
The Lindsay Lohan you see today is completely different from 2007-era LiLo. Reflecting on her past, she told Wendy Williams that she "didn’t really have a private life" when she was young so she’s now happy to be in control of that.
She’s also taken multiple breaks from social media and spends a lot of time doing charity work in Europe and the Middle East.
Neverending Boy Troubles
Back when these three were at the top of their game, Lindsay, Hilary Duff, and Ashlee Simpson were involved in the most 2000-era love triangle.
Lindsay and Hilary fought publicly in 2002 after Aaron Carter was exposed to be dating them both. Then two years later, Lindsay and Ashlee got into a catfight over Wilmer Valderrama.
A Controversial Photoshoot
Lindsay has been known to push the boundaries creatively when it comes to photoshoots, but one particular shoot from 2012 took it too far. Photographer Terry Richardson published photos that showed Lindsay holding a handgun and appearing to portray suicide.
The public lashed out for her insensitivity.
Becoming Marilyn Monroe
Lindsay has channeled fashion icon Marilyn Monroe not once, but twice. The first was in 2008 for a recreation of Monroe’s famous final photoshoot. The original photographer, Bert Stern, even came back for the shoot.
The second time, in 2011, was for a Playboy cover shoot. Needless to say, Marilyn Monroe’s longstanding fans found the photoshoots insensitive.
Crossing The Aisle, Well, Kind Of
Celebrities are known for speaking out when it comes to politics, and Lindsay did just that when she offered to campaign for Barack Obama in 2008. Unfortunately for Lindsay, he didn’t want her help.
She must have been pretty ticked off about it because she flipped sides and officially supported Mitt Romney in the 2012 election.
Betrayed By Her Dad
Lindsay’s relationship with her dad Michael has always been rocky, but 2009 was an especially bad year. Michael betrayed his family and sold taped phone conversations between him, his wife Dina, and Lindsay.
On the tapes, you can hear Lindsay crying hysterically and complaining that “no one cares about me.” Not cool, Michael, not cool.
Not So Friendly With The #MeToo Movement
2017 was a monumental year for women in the entertainment business, and all around the world, with the advent of the #MeToo movement. When asked about her experience in the industry, Lindsay said that she had nothing negative to say.
That would have been fine, but she went the extra mile and said that some women go to the police “for attention” and that they are “weak women.” Yikes. So much for solidarity, Lindsay.
Finding It Hard To Keep A Job
Even if Lindsay wanted to mount a comeback in the entertainment industry, it seems like she’d have a very difficult time. Lindsay has been fired from multiple films over the years since her downward spiral started.
Most recently, she signed on to portray the controversial adult film star Linda Lovelace, and was fired and replaced by another blonde, Amanda Seyfried.
A New Reality Show In The Works
It appears that Lindsay’s return to entertainment will happen in the form of a reality show. “Lohan Beach Club” is set to air on MTV in 2019. It’s basically a reality show that follows Lindsay and her life in Mykonos.
Fans are anxiously awaiting it after a clip of Lindsay dancing in Mykonos went viral and turned into a certified meme.
A Controversial Refugee Video
Lindsay is reportedly very invested in the Syrian refugee crisis, but we’re not so sure after a video of her and a Syrian family went viral. In the Instagram live video, Lindsay appears to be welcoming a family she met on the street and offering them food and a hotel.
Then she suddenly turns around and accuses the mother of trafficking the children. The video ends with the mother punching Lindsay for trying to take her kids.
A Shrewd Businesswoman
It doesn’t look like Lindsay will return to the big screen anytime soon because she seems to be enjoying the entrepreneur life. In 2016, when deciding what business to invest in, she asked herself “what would people expect me to do?”
That’s why Lindsay is now the proud owner of multiple name brand nightclubs, with the next set to open in Lebanon.