20 Photos Of Lindsay Lohan Crashing And Burning

Lindsay Lohan, or LiLo as she is not-so-adorably known, is one of the most infamous examples of celebrity life gone wrong. It seemed like she had it all. As a teen, she became a superstar, appearing in hit movies and generally having the time of her life. She was getting great roles, hanging out with other A-listers, and spending half her time partying.

Unfortunately, as can often be the case when you have more money than you’re supposed to at that age, the partying started to become more than half her life. It started to take over, to the point where it was getting her into trouble for showing up on set late. Then she started getting caught with drugs, and crashing cars, and it all went downhill from there.

For someone who was on probation for almost all of her life as a legal adult, you would think that Lindsay would calm down. But she didn’t. She just kept spiralling down and down and down, and the whole world was watching her do it. We have the mugshots to prove it. Even when the work started drying up and her friends started abandoning her, Lindsay wasn’t able to see the signs. She couldn’t turn her life around, and spent the best part of a decade in a lot of trouble.

We’ve gathered the juiciest bits from her history right here for you to see. Watch as a happy young woman transforms into the most troubled celebrity since Britney!

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20 Fame With Mean Girls

In 2004, it seemed like Lindsay had everything possible going for her. She starred in Mean Girls, the teen hit that turned into a huge career boost not only for her but also for Amanda Seyfried, Rachel McAdams, and more from the cast. The film has gained a cult status today and is still hugely popular. This was, however, not the starting launch pad for her movie career, but actually the highest point. She failed to capitalize on the opportunity, with her bad behaviour beginning around this time. At the age of 17, she moved in with her boyfriend, Wilmer Valderrama – many might say far too young. Their relationship only lasted for a few more months before they split up, which may have been one of the catalysts for her later behaviour.

19 Dramatic Weight Loss

After her break-up, and while hanging around with other starlets like Paris Hilton and Nicole Richie, Lindsay started to lose a noticeable amount of weight. She dropped the pounds so quickly that rumours of anorexia or drug use quickly started to fly – with many now of the opinion that this was the point she started to use serious drugs. She brushed off the weight loss by saying, “I got a trainer … Just old-school working out.” However, things were obviously not as good below the surface as she pretended. Her father, Michael Lohan, was sentenced to one and a half years in prison in May 2005, for aggravated unlicensed driving and attempted assault. That must have been weighing on her mind, and the last thing that she needed was another traumatic incident at this point.

18 Paparazzi Van Crashes Into Her Car

On the 31st May 2005, Lindsay was involved in an accident when a paparazzo deliberately hit her car with his van. She only suffered minor injuries, though the car was seriously damaged. The driver was arrested for assault with a deadly weapon as a result of his intentional charge. Around this time, her career seemed to still be going well. She starred in Herbie: Fully Loaded, though the film and her performance faced criticism, and became the first celebrity to have her own My Scene doll. During the rest of 2005, her parents were divorced, leaving her father without a share in her earnings, and another car accident that was not her fault saw her black Mercedes damaged once more. She released her second studio album, including a song dedicated to her father.

17 Fallout With Paris Hilton

In May 2006, the relationship between Lindsay and Paris seemed to sour. They fell out and soon let the whole world know about it. Friends of Paris called Lindsay names to reporters, while Lindsay tried to stay above it all. She accused Paris of sending her prank voicemails, and refused to watch clips captured by reporters, saying, “Obviously, she’s very comfortable making videos.” Around this time, she was still filming movies, but was starting to struggle with her schedule. She was hospitalized for exhaustion and dehydration before things started to go even further downhill. It’s easy to see at this point how family troubles, public spats, drug use within a partying lifestyle, and her movie schedule began to take too much of a toll on her health. With hindsight, a break from acting might have been a better choice.

16 Stern Warning On Set Of Georgia Rule

GEORGIA RULE, Jane Fonda, Lindsay Lohan, 2007. ©Universal

While Lindsay was filming Georgia Rule, a leaked letter from James G Robinson of Morgan Creek Productions goes public. Part of it reads, “Since the commencement of principal photography of Georgia Rule, you have frequently failed to arrive on time to the set. Today, you did not show for work (all day). I am now told you don’t plan to work tomorrow because you are 'not feeling well'. You and your representatives have told us that your various late arrivals and absences from the set have been the result of illness; today we were told it was 'heat exhaustion'. We are well aware that your ongoing all night heavy partying is the real reason for your so called 'exhaustion'. We refuse to accept bogus excuses for your behavior.” Whether the accusations were founded in truth or Lindsay really was struggling, the public denouncement had a knock-on effect on her career.

15 Arrested For DUI And Caught With Illegal Substance

After ongoing spats with Paris Hilton, which saw Lindsay accusing her of hitting her with a glass and pouring a drink all over her, Lindsay had her first arrest. Her mugshot was shocking – she appears to have poor skin, bedraggled hair, and a confused expression. She was charged with driving under the influence and possession of cocaine after losing control of her car in Beverly Hills and crashing. Video footage of the incident and her arrest surfaced online after the paparazzi who were following her filmed it all. She was given a suspended license for the incident on the 26th May 2007, but sadly this was not to be the end of her car troubles. Just as Amanda Bynes seemingly could not stop getting behind the wheel even when told not to, Lindsay couldn’t get the message that she was not to drive.

14 Second Arrest For DUI

Lindsay’s second arrest, also for driving under the influence and possession of cocaine, happening on July 24th, 2007. This was less than a month after she was first caught, and a charge of driving on a suspended license was added to the tally. She was caught after chasing an SUV at a high speed, exactly the kind of behaviour which is guaranteed to get the attention of the police. This time, her mugshot appears more defiant, a trend which would continue. She said, “It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs. Recently, I relapsed and did things for which I am ashamed. I broke the law, and today I took responsibility by pleading guilty to charges in my case. No matter what I said when I was under the influence on the day I was arrested, I am not blaming anyone else for my conduct other than myself.”

13 Relationship With Samantha Ronson

After serving an impressive 84 minutes in jail, Lindsay seemed to put the incident behind her. During the summer, she ended up getting into a relationship with Samantha Ronson. The fact that they were both women, and that Lindsay had so far only been linked with men, was highly controversial. Many suggested that Lindsay was having some kind of breakdown. Their relationship was very much on-and-off, with plenty of dramatic break-ups and make-ups. Though they never publicly confirmed a romance, they had plenty of fights in public – and eventually even took to Twitter to air their grievances against one another. They also appeared posing together many times. Lindsay said, “I need to love myself first before I could be with anyone else, and I was going through a lot. Two toxic people cannot be together. End of story. We're friends now. That's how it started so I think that's how it was meant to be.”

12 Labor Pains Goes Direct To TV

Lindsay made an effort to revive her career after all of her legal troubles in 2009. Sadly, that didn’t go quite as planned. Though Labor Pains was slated for a cinema release, it ended up going straight to being a TV movie. A couple of months before the eventual release, she faced potential arrest after being suspected of breaking the terms of her probation, but managed to avoid it after her attorney spoke on her behalf. Her probation was due to end in 2009, but then was extended for 12 months because she failed to complete the alcohol education program that she had been ordered to attend. This little blunder ended up getting her in more trouble than she realized, as it meant that her probation extended into 2010 – which would later prove to be very important.

11 Cannes Film Festival Blunder

Lindsay attended the Cannes Film Festival in 2010 and was pictured partying with friends, a blunder that would soon have serious consequences. She missed a mandatory court hearing while she was there. She claimed that she could not make it back to the court in time because her passport had been stolen, but the paparazzi photos did not go in her favour. The judge revoked her probation and issued a warrant for her arrest, with bail set at $100,000. It seems that Lindsay never manages to learn the lesson that her behaviour will bring consequences, as this was not to be the last time she was caught partying when she was supposed to be on probation. She was duly arrested and paid the bail fee to get out of jail, but would soon be back in court again as a result of further orders and restrictions.

10 Wearing A SCRAM

One of the conditions of her release was that she would have to wear a SCRAM device, otherwise known as an ankle bracelet – and not the fashionable kind. This was to monitor her alcohol consumption to ensure that she was not going outside of the terms of her probation. She was also required to undergo drug tests once a week as part of the terms. A month after having it fitted, on June 6th, 2010, she attended the MTV Movie Awards wearing a long pantsuit that hid her bulging SCRAM from sight. Later, she caused a bit of a fashion stir by having a series of small Chanel bags made which fitted over her SCRAM to match whatever shoes she might be wearing whilst out and about. It sounds like the ultimate extravagance – being rich enough to cover up your punishment.

9 90 Days In Jail

Unfortunately, going to the MTV Movie Awards afterparty wasn’t the best move for Lindsay. Her SCRAM lit up because she had too much to drink, and she was found to be in violation of her probation. Her bail was raised to $200,000 and she was arrested again. As a result of this, and the fact that she still had not gone to her alcohol education course, she was sentenced to 90 days in jail on July 6th 2010. She surrendered on the 20th and ended up being in prison for two weeks. Due to overcrowding, all of her jail sentences have turned out to be much lighter than first proposed. Many have cynically suggested that she was given lighter sentences and let out earlier because of her celebrity status.

8 Going Into Rehab

When Lindsay was put back on probation after coming out of jail, she managed to stay on the straight and narrow – for all of one month. She then tested positive for cocaine in a routine drug test that was part of her probation on the 24th September 2010, which was a violation of her terms. She was put into jail temporarily but her attorney argued for her to be allowed to go into rehab. On the 28th September, this was allowed. There is more open defiance in her gaze for this mugshot, as she is probably starting to get used to the procedure of going into jail regularly now. It’s likely she wasn’t even surprised, since the tests were done regularly and she had to know it would catch her out.

7 The Stolen Necklace

On February 9th, 2011, Lindsay was arrested yet again. By this point it was clear to anyone that her life was desperately out of control. No amount of punishment seemed to be working, and something was going to have to change if she was going to get back on track. This arrest was in connection with a theft of a necklace from a jewellery store, to which she pleaded not guilty. She ended up not seeing any follow-up on the jewellery store arrest, although she was in and out of court throughout the first part of the year, often looking tired and frail.

6 A New Day, A New Mugshot

By this stage, it was all just getting too much like a normal routine. On the 19th of October 2011, she was found to be in violation of the terms of her probation yet again. She was placed under arrest after facing a judge in court, and then led out of the courtroom in handcuffs. She was released after her bail of $100,000 was posted. At this point you have to wonder how an actress who really wasn’t getting much work at all could continue to afford this bad behaviour. She looks washed-out and pasty without her usual fake tan in this shot, with large bags under her eyes and poor skin. She is really beginning to look less like a Hollywood star and more like a criminal drug addict who just can’t stop getting arrested.

5 Fighting With Her Mother

Another month in prison for breaking the terms of her probation. Another probation revoked which saw her released on bail after she failed to complete her community service hours. Time on house arrest. Another alleged car accident which was never proven. Another (!) alleged car accident. Time just flew by for Lindsay when she was having fun, right up to the 10th October 2012 when she had a fight with her mother, Dina. The fight was so bad that police were called, though no charges were brought. Somehow she just kept on breaking the law and getting away with it – when you see it all written out on paper it begins to look absolutely ridiculous. How could someone break their probation so many times that they end up staying on probation for five years for one incident?

4 The Canyons: A Career Low?

Something of a “revival” happened for her career in 2012, although the films she managed to land were nothing compared to her earlier work. In November 2012 Liz & Dick, a TV movie in which she played Elizabeth Taylor, was released. In April 2013 she was in Scary Movie 5 alongside Charlie Sheen, which is all you need to know about how far her star had fallen. Then she hit what has to be the lowest point of her career so far, in The Canyons. The film, which sees adult star James Deen crossing over to the mainstream, barely remains in the camp of an art film rather than an adult one with plenty of full-frontal nudity. Not the kind of fare she would have been offered after Mean Girls.

3 Boating Accident Severs Her Finger

Even though she seems to have got her legal troubles under control for a while, there were soon plenty of health issues waiting to strike Lindsay. First, she was hospitalized after she contracted Chikungunya disease in French Polynesia, in January 2014. Then she was involved in a boating accident in October 2016 which saw half of her ring finger being severed! It was recovered and then reattached in hospital, but it could have caused permanent damage. Still, she did have something to celebrate: her probation had ended in May 2015, which meant that for the first time in eight years, she was at last not under watch. The good news is that she did not return to her bad behaviour as soon as she got the chance. At least, she wasn’t caught, at any rate.

2 On The Beach In A Burkini

She was seen holding a copy of the Quran in April 2016, fuelling rumours that she was converting to Islam. This speculation only continued to mount when, in January 2017, she deleted all of her Instagram posts but one. The one that remained read ‘Alaikum salam’, which is Arabic for ‘peace be with you’ and is a common Muslim blessing. In February 2017, she claimed that wearing a headscarf in London’s Heathrow Airport had led to her being racially profiled. In April, she made bigger waves by going paddle-boarding in Thailand – wearing a burkini. This outfit, which allows the wearer to adhere to the Muslim dress code while still being convenient for water sports, was an odd appearance as she seemed to deliberately pose for reporters.

1 Questioned About Another Theft

Just when you thought all of her troubles were over, they seemed to come right back on again. On June 10, 2017, it was revealed that she had been questioned by police about another theft. This time, $24,000 worth of Egor Tarabasov’s belongings had gone missing – and if you’re wondering what that has to do with her, Egor was her ex-fiance. It then turned out that he had left the belongings in her apartment when he stormed out during their final fight, and as soon as the police asked, she simply gave the items back. Their relationship was troubled by all accounts, with public fights and accusations of domestic violence. What will happen to her next? That’s up to her, but she is going to need to work hard if she wants to get anywhere near her former position in the industry.

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