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BREAKING NEWS

The Loh-Down On Lindsay Lohan: Then And Now

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Oct. 11 2018, Updated 3:31 a.m. ET

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Oh, Lindsay Lohan! That hot and beautiful mess we simply cannot take our eyes off of! Lohan has made many headlines since she broke out with the 1998 movie The Parent Trap and now she’s a major household name.

MORE: Lindsay Lohan Attending ‘Mean Girls’ Broadway Performance After Tina Fey Snub

Her journey in the spotlight has so far given us many highlights and lowlights, some of which we are going to look at here. From DUIs to boozy brawls; to being the victim of burglars (remember the Bling Ring?) to dating all manner of celebs and even to defending Harvey Weinstein, Lohan is rarely out of the news.

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MORE: Kim Kardashian Slams Lindsay Lohan For ‘Confusing’ Foreign Accent

Let’s take a stroll down memory lane from then to now and see why we love the car-crash celebrity lifestyle that Lohan encapsulates—but also how, like a phoenix, she has risen from the ashes. Repeatedly.

1. Mean Girls

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Lohan began her career at age 10—she was a celebra-tot—but her biggest splash came at 18 when she starred in Mean Girls. She let it all hang out at the premiere—guaranteeing press for days! Nip slips for the easy publicity win.

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2. DUI #1

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At 21 years of age, Lohan was arrested for drunk driving and cocaine possession. Police spotted her SUV chasing another vehicle at high speed so she was pulled over and she failed a field sobriety test (probably because she didn’t have time to study). After being escorted to the L.A. County lockup, a pat-down revealed cocaine in her pants pocket.

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3. Wax And Wane

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For Lohan’s 20th birthday, Madame Tussads revealed a wax figure of the starlet that came with an interactive element. No words on what Lohan thought of herself as a fancy candle.

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4. Broken Wrist

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In 2006, Lohan fractured her wrist in two places after falling at Milk Studios in NYC during fashion week. Here she is hiding the cast she had to wear until it healed under a sweater. What could have been written on it that she had to hide it from photographers?

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5. Courtenay Semel

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Lohan and her then-gal pal Courtenay Semel were spotted out at a Hollywood nightclub enjoying a night out together. Semel has reportedly called herself the “Don Juan of the lesbian world” and has also dated Tila Tequila.

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6. Rehab No No No

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In January 2007, Lohan checked herself into the Wonderland Treatment center in West Hollywood so she could get healthy. It didn’t quite take as she was about to embark on a bumpy ride in and out of jail, courts, and rehab. Buckle up.

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7. Mowing Paparazzi

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In March of 2007, Lohan left a NYC nightclub in her BMW and tried to escape the paps who surrounded her. She led them on a car chase, reportedly running red lights and driving the wrong way down a one-way street until she was pulled over by the cops. Her car lurched forward, hitting a photographer and injuring him but the police let her go.

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8. DUI #2

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Lohan got her second DUI in less than three months with a reported blood alcohol level between .12 and .13 (well over the .08 legal limit). She was also reportedly found to have a controlled substance in her possession. Making matters worse, Lohan’s assistant Jenni Muro (who is pictured on the left) had quit hours earlier and when Muro’s mom came to pick her up, Lohan allegedly gave chase. Mom called the cops and headed towards the nearest police station which ended with Lohan’s arrest.

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9. DJ Love

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For a while, Lohan dated DJ Samantha Ronson. Here they are at The Plumm, an NYC nightspot in 2007. Together, they spun great music—until the (cat) scratching got in the way.

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10. Simply The Best

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Lohan also dated Calum Best, son of ace soccer player George Best, in May 2007. Calum, a known ladies man, has since said he’s left his womanizing past behind him. Here they are having lunch in NYC with Kylie Minogue.

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11. Rehab Yes Yes Yes

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Lohan landed back in rehab—this time in Malibu—in June 2007. She reportedly checked herself in after her DUI and suspicions of cocaine abuse. She could have saved herself a lot of money because things were about to get worse, not better.

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12. Court Battle

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That same month, Lohan’s parents were battling it out in a Long Island court over visitation rights of their younger children (Michael, 19, Ali, 13, and Dakota, 10). As Lindsay was no longer a minor, she was not caught up in the dispute.

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13. 21st Birthday

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A few weeks after that court battle, Lohan turned 21 and took a break from her stint at the Malibu treatment facility to party. She also turned the cameras back on the paparazzi so they could get a sense of how it felt being watched all the time! Sadly no publication wants to pay for pictures of unwashed photographers, no matter who took them.

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14. Ankle Bracelet

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Lohan showed off her alcohol-monitoring bracelet that she allegedly chose to wear to ensure no one questioned her sobriety at various events and functions she was attending. Only Lohan could make an ankle-bracelet look good.

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15. Wax In Jail

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Madame Tussauds made sure Lohan’s wax figure’s outfit was updated and made as topical as possible when they dressed her in a comedy jailhouse costume. Stick a wick in it, Madame Tussauds because that’s a classic burn!

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16. A New Rehab Yes, No, Yes!

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By August 2007, Lohan’s “annus horribilis” saw her back in rehab—a different one, this time, in Utah. Here she is reading the AA’s Big Book. Spoiler: the butler did it. With a bottle of vodka.

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17. Detention Center Certificate

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In November 2007, Lohan turned herself into the L.A. County Women’s Detention Center where she served a massively long sentence of, ooh, eighty-four minutes. That’s less than most of her films, some of which feel like a jail sentence in and of themselves!

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18. Making Music

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Life wasn’t all rehab and stints in jail. Lohan returned to the studio in December 2007 to record a new album. A single was released called Bossy that was co-written by Ne-Yo but it failed to chart and ultimately the album was never released. That’s how good it was.

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19. Italy

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Lohan was hanging with her gal pal Courtenay Semel in Dec 2007 for a New Year’s Eve trip to Capri in Italy. She went to the Capri Film Festival where she was being honored along with Dennis Hopper, John Malkovich, and Hayden Panettiere.

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20. Traffic School

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Lohan donned a black wig to attend Traffic School in Santa Monica. It was part of her DUI bust earlier in 2007. The wig came very close to landing its own reality show but it was ultimately given the brush off.

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21. Fashion Show Spill

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Lohan was at a fashion show when someone spilled a vodka and Red Bull on her—so she stormed out five minutes later. Presumably, she got home and changed into an outfit that was clean. And sober.

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22. Ugly Betty

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Lohan appeared in Ugly Betty in 2008—here she was on set before cameras rolled. She was set to appear in six episodes but according to reports, producers cut her down to four episodes because she clashed with star America Ferrara and producers.

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23. Labor Pains

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Lohan starred in Labor Pains that was released in the US on ABC Family. In the movie, Lohan played a woman who fakes a pregnancy to keep her job. Her work in the movie I Know Who Killed Me earlier that year won eight Golden Raspberry Awards including worst film, worst actress and a newly-created award for worst excuse for a horror movie.

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24. MTV VMAS Again

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Lohan looked ever so glamorous at the 2008 MTV Video Music Awards. Her outfit fit like a glove and she turned heads wherever she went. Not pictured are the zips on the butt because there aren’t enough designer dresses out there with butt-zips. Maybe next year.

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25. Call The Cops!

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In September 2008, Lohan was at the Bowery Hotel in NYC attending Marc Anthony’s birthday bash (he was there with his other half Jennifer Lopez). Unfortunately, one thing led to another, and Lohan got into a fight with a photographer and called the cops on him.

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26. Fiiight!

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Lohan and her then-girlfriend Samantha Ronson got into some kind of spat at a party in NYC. Ronson stormed out of the party but Lohan was close behind, running after her and screaming her name. They reportedly argued, with Lohan repeating “Don’t do this to me, Sam!” over and over. The argument continued as they made their way several blocks back to their hotel.

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27. Community Work

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In March 2009, Lohan was snapped leaving her house to head to Glendale’s Traffic Community Service Center. She had lots to work through for her accumulated DUIs and arrests.

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28. Red Bull

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Exactly one year later, in March 2010, Lohan was attending Milan Fashion Week in Italy. As she hopped in her car to head to the airport, she tossed a Red Bull at photographers before driving off. That's some red bull-s**t!

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29. In Court

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Lohan got her day in court a little later than intended after getting stuck at the Cannes Film Festival because she lost her passport. Lohan had new bail conditions imposed, including a drinking ban, random weekly drug testing and a bracelet to detect alcohol.

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30. DUI Classes

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A week later, Lohan was papped as she arrived at her drug and alcohol class that the judge had ordered her to attend. No word on what she may have learned there but her problems with drugs and booze would continue.

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31. VMAs Take 2

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Lohan looked stunning and sparkly in this slinky outfit as she appeared on the red carpet at MTV’s Video Music Awards in 2010. That year, she opened the show appearing in a skit that was funny and self-deprecating.

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32. Alcoholics Class

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Lohan looked simply gorgeous as she arrived at the Right On Programs alcoholics class in Los Angeles. She clutched a bottle of Tru-Blood and a pack of ciggies. Tru-Blood was actually a non-alcoholic carbonated drink inspired by the HBO series of the same name that was dubbed as “all flavor, no bite.”

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33. Jail

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In July 2010, Lohan left the L.A. courthouse after being sentenced to 90 days in jail. The judge demanded it after Lohan missed alcohol counseling sessions—in direct violation of her probation. Lohan was also ordered to spend 90 days in a drug and alcohol rehab program after her jail term is completed. "I did do everything that I was told to do and did the best I could," sobbed Lohan—who was later revealed to have a profane message painted on her fingernails for the hearing.

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34. Those Nails

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And what was written on her fingernails? You’ll have to zoom in pretty tight but there, on her middle finger nail of her left hand is a certain four-lettered epitaph. Not necessarily the best move in a court of law but one Lohan reportedly pulled off while sitting in the courtroom—and while her lawyer appeared, at times, to intentionally position herself between Lohan and the cameras.

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35. A New Headshot

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Lohan poses for yet another mugshot—this one courtesy of the L.A. County Sheriff’s Department. She was ordered to serve three months in jail after a judge determined that she had violated the terms of two (two!) DUI arrests.

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36. Orange Is The New Black

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Another day, another mugshot. In September 2010, Lohan was ordered to jail yet again for probation violation. She managed that by failing two different drug tests after she was released from prison in July. She was told to stay there until her hearing the following month.

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37. Probation Hearing

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That October 2010 probation hearing resulted in Lohan being ordered to stay at the Betty Ford Clinic until January in lieu of jail time. Lohan looked casual-smart as she was flanked by lawyers.

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38. Necklace Theft

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Lohan appeared in L.A. Superior Court in March 2011 after allegedly taking a $2,500 necklace from a jewelry store in Venice, CA. This was her ninth court hearing in ten months! Lohan rejected a plea deal and the case moved forward.

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39. Community Service

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Lohan’s necklace theft charge was reduced to a misdemeanor and she was ordered to perform 480 hours of community service. Here, Lohan heads off to the Downtown Woman’s Center in L.A. to start the work program.

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40. Cannes Do Attitude

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Lohan attended the 2017 Cannes Film Festival and looked radiant with a new, shorter hair cut. Has she left all her troubles behind her? Only time will tell.

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