www.thethings.com

15 Of The Most Jaw-Dropping Things Lindsay Lohan Has Ever Done

For over 10 years, Lindsay Lohan has been plagued with legal trouble, nip slips and celebrity excess—fascinating us all with how quickly she went from child star to trainwreck. She's a classic example of why drugs are bad, mm'kay? Every other celebrity's drug and alcohol addiction pales in comparison to LiLo's time in and out of rehab, prison and house arrest (except maybe Robert Downey, Jr.). She just could never seem to make sobriety stick and as a result, she did some pretty jaw-dropping things that would shock even Charlie Sheen. We've compiled a nifty list of some of her most WTF moments that will make you giddy with gossip. Regardless of what you think of Lindsay, you have to admire how she just doesn't give AF what anyone thinks. If you take anything away from this list, let it be that.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Lindsay Lohan Butt Flash Kids Choice Awards
Start Now

15 Flashing a bunch of children at the Kid's Choice Awards

Lindsay Lohan Butt Flash Kids Choice Awards
Via: gawker.com

No stranger to nip-slips, side boob and the like, Lindsay Lohan shocked the world when she accepted the Favorite Movie Actress award for her role in Herbie: Fully Loaded. As she bounced her way up the stage in a gold ruffled dress, it rose up a little higher than expected. As a result, Lindsay flashed not only photographers and her fellow nominees, but thousands of children in the audience and on TV. It wouldn't have been such a big deal if she was actually wearing underwear, but LiLo has become famous for going commando when wearing a dress or skirt. Instead, she likely traumatized girls and boys alike with a view of her pale behind in all its glory.

The best part is that a contortionist came out almost immediately after she accepted her award and put her head through her legs, with her a** facing the audience. For anyone who fetishizes butts, the 2006 Nickelodeon Kid's Choice Awards was a wacky display of derrière worship largely due to Lohan's indiscretion.

14 Getting arrested and jailed multiple times

Lindsay Lohan Mugshots
Via: cnn.com

Lindsay Lohan may just hold the record for most celebrity run-ins with the law. From 2007-2012 alone, the Freaky Friday actress appeared in court a jaw-dropping 20 times for DUIs, grand theft and violating her probation. LiLo also spent two weeks in jail, although not consistently, due to overcrowding. You'd think she would have learned after the first time, but Lindsay obviously doesn't give AF about following the law. As a result, she was sentenced to house arrest and community service at both a women's center and the city morgue of all places, to try and give something back in exchange for her lawlessness.

Since she had multiple DUIs and failed a ridiculous amount of drug tests while on probation, Lindsay spent nearly a year of her life in and out of rehab centers, trying to get clean. However, it seems like she finally has her act together now (more on that later). This year, she has a reoccurring role on the UK show Sick Note with Harry Potter alumnus Rupert Grint, and will have her first starring role in four years in The Shadow Within, a horror-crime film. We're rooting for you, LiLo!

13 Telling a judge she can't afford therapy while wearing $1200 shoes

Lindsay Lohan Shows Up to Court in Christian Louboutins
Via: loverofgossip.blogspot.com

Celebrities, they're just like us. They, too, can't afford their court-ordered therapy sessions and arrive to their hearings wearing a pair Christian Louboutins. Wait, what? Yes, this is something that LiLo actually did in 2011. The young actress was in and out of court for various crimes, including the theft of a $2,500 necklace from an artisan jewelry store in Venice, CA.

On one such court appearance, she arrived in a long black dress, leather jacket and a pair of $1,200 Christian Louboutin heels to check in with the judge. According to Perez Hilton, she was praised for attending a shoplifter's alternative course and doing community service, but hadn't yet started her court ordered therapy. Her excuse? She didn't have the money because her Screen Actor's Guild insurance had expired and she couldn't afford the out of pocket expense. This coming from the girl who was earning half a million dollars per film when she was 17 years old. Sell those shoes, girl! Stylish to the very end, isn't she?

12 Working with the homeless in a see-through top

Via: dlisted.com

At the peak of her disregard for the law, Lindsay Lohan was sentenced to community service at the Downtown Women's Center in Los Angeles. In classic LiLo style, Lindsay showed up to her orientation braless (as usual) and wearing a partially see-through tank top. Needless to say, all those homeless women she likely encountered, along with the staff of the center, got a full view of Lindsay's boobs—nipples and all.

You'd think her lawyer (seen behind her in the sunglasses), would have advised her to wear something a little more conservative for her first day of service, but Lindsay doesn't seem the type to listen to good advice when she hears it. In all likelihood, she wore the outfit just for the scandalous tabloid headlines and so the paparazzi would have a field day trying to get a clear shot of her braless knockers. One things for sure, she's not ashamed to flaunt what she's got.

11 Filming sex scenes with porn stars for $100 a day

Via: nytimes.com

After most of her troubles with the law were through, Lindsay tried to make a comeback in 2013 with Paul Schrader's film The Canyons. As you might imagine, it was pretty disastrous for everyone involved, including Lindsay. In fact, an entire New York Times article was written about the experience of making the film with Lindsay and how much of a liability she was. Amid all the not showing up for work and partying with Lady Gaga when she had a 6 a.m. call time the next day shenanigans, Lindsay did something even more shocking—even for her.

She agreed to do the film for a measly $100 a day and participate in a contractually obligated four-way sex scene with three porn stars. Granted the film only had a $250,000 micro-budget, but still. Most celebrities would have balked at that rate, which is normal when you're just starting out, but not when you were a child star and had top-billing only a few years prior. It was clearly the act of a desperate woman, keen on re-starting her career by way of her naked body.

10 Revealing deeply personal info on her OWN reality show

Via: oprah.com

Somehow, Lindsay got her own reality show on Oprah's OWN network mere weeks after her latest rehab stint in 2014. Intended to last for at least 12 episodes, the series only made it to eight due to Lindsay having a meltdown in the middle of the season and holding up production for two weeks. Apparently there was a very good reason for the delay, at least according to LiLo.

In an announcement at the end of the show, she revealed that she suffered a miscarriage while filming, which left her sick and depressed—unable to appear on camera. That meant that she had to have been pregnant while they were filming the show and possibly even before that in rehab. It's a pretty big revelation considering her spotty past with men and frequent public nudity.

9 Making a list of famous men she'd boned

Via: complex.com

During the filming of her reality series, Lindsay made major headlines once again when a list of rich and/or famous men she boned was leaked online. Apparently, she wrote the list while playing board games with some friends at the Beverly Hills Hotel. Her list includes some pretty notable names including Justin Timberlake, Ashton Kutcher and Orlando Bloom, whom she inevitably banged at the height of her stardom (and before any of them got married—we hope).

Missing from the list were female names like Samantha Ronson and Courtenay Semel, so this was undoubtedly a "d**k list." Over 36 men were publicly revealed to have slept with LiLo, which seems like an awful lot even for a party girl. No judgement, though! When you're surrounded by that many beautiful people all the time, it has to be hard to control yourself.

8 Claiming to have saved 40 children from an Indian sweatshop

Via: bbc.co.uk

Likely the result of her constant need for attention, Lindsay pissed off a bunch of Indian activists when she claimed to have personally saved 40 children from an illegal sweatshop. As part of a BBC documentary filmed in 2009, Lindsay traveled to India to investigate child trafficking—an issue apparently close to her heart.

In an article by the UK's Telegraph newspaper, Lindsay was quoted as saying, "Over 40 children saved so far...... Within one day's work...... This is what life is about..... Doing THIS is a life worth living!!!" According to the charity that organized the sweatshop raid, Lindsay wasn't even in the country when it happened and claimed she wasn't even aware of the location of the sweatshop. At least she didn't pull an Angelina Jolie and take all the kids home with her.

7 Calling a famous fashion designer a "Russian hooker"

Via: mirror.co.uk

Last year, Lindsay's engagement to Egor Tarabasov, heir of a large Russian fortune, abruptly came to an end after a physical altercation was caught on camera. The couple was seen on a beach in Mykonos, Greece fighting over Egor's phone, which Lindsay had taken and tried to run off with. Shortly after, she took to Instagram and Twitter to publicly deride her fianéce and accuse him of cheating on her with a "Russian hooker."

Well the woman she tagged was actually a friend of theirs, Dasha Pashevkina, a UK fashion designer known for her Pa5h line. Dasha denied all claims of involvement with Lindsay's fiancée, but she must have seen something on that phone of his to make her think otherwise. Apparently, she even tweeted the designer's personal information before quickly deleting it from Twitter, which leads us to her next jaw-dropping moment(s).

6 Constantly deleting her most WTF tweets

Via: huffingtonpost.com

You could plaster an art gallery's walls with Lindsay Lohan's deleted tweets. They are many and varied, from encouraging people to visit Uganda to asking Chanel to give her stickers for her house arrest bracelet. Lindsay has often tweeted without a filter, and later regretted it, but the internet never forgets. Buzzfeed compiled a bunch of deleted tweets in a single, hilarious post that provides a bizarre look into the mind of a troubled celebrity.

Although she's certainly not the first to do so, Lindsay's deleted tweets are pretty entertaining, especially because many of them were written while she was at her worst. Not to diminish all her suffering, but like they say, pain often produces the best art—and when examined with a critical eye—she's created a pop culture masterpiece.

5 Flashing her crotch not once but three times at the paparazzi

Lindsay Lohan Crotch Flashes
Via: gawker.com

No celebrity name has become synonymous with crotch shots as much as Lindsay Lohan's has. After the success of Mean Girls and amid her attempts at a singing career, Lohan had a number of particularly jaw-dropping photos come out of her formerly private parts. Each time, she was wearing a dress or skirt and seemed to have conveniently forgotten to put on underwear. Needless to say, in 2006, the paparazzi caught sight of her lady bits a record three times as she was exiting boats and limousines.

Lindsay commented on the first photo via Elle magazine. "I was rushing through the room, threw the Prada dress on. And that's what happened. And I didn't even see the picture," she explained. "I don't look at that s**t—that's gross. If I wear a dress I have underwear on." Nevertheless, she disapproved that statement time and time again, which has to make you wonder if she even owns a pair of underwear.

4 Racking up a $46,000 bill at a famous Hollywood Hotel

Via: la.curbed.com

After one of her rehab stints, Lindsay checked into the Chateau Marmont, a famous Hollywood hotel known for its celebrity clientele. However, instead of taking her sobriety seriously and staying out of trouble, she racked up a $46,350.04 bill during her 47-day stay at the hotel. That's about $1000/day of charges, which is like the equivalent of the average person paying their rent every day of the month.

The 16 pages of charges included multiple mini-bar purchases, which may or may not have been alcohol (mini bar refers to any consumable item left for guests). There were also $14 packs of cigarettes, a $100 candle, iPhone chargers, parking, room service and TV/internet purchases. Lindsay was effectively banned from Chateau Marmont until she paid her incredibly high balance, which she did manage to do a few months later.

3 Yelling racist insults at an NYC bartender

Via: mirror.co.uk

More recently, Lindsay went on a racist tirade, attacking a New York City bartender in Greenwich Village. Lindsay and her sister, Ali, locked themselves in the bathroom for over 20 minutes (likely doing coke), until the bartender asked them to leave. She then started yelling things like, "This is New York. You’re not from here," and asking him if he was from Ghana.

When a few of the bar patrons tried to stop the sisters, Lindsay responded by spitting in their faces. Even when they finally left the bar, they continued to harass people from outside—filming them with their phones and banging on the windows. It was not a pretty sight and was further tabloid fodder for the 30-year-old actress as she struggled to find work last year.

2 Talking in a bizarre accent

Via: dailymail.co.uk

At the end of last year, fans and reporters alike were thoroughly confused when LiLo started talking in a bizarre accent during interviews. It all started at the opening of her new nightclub in Athens, Greece—a joint effort with Greek restauranteur Dennis Papageorgiou. Her accent sounds decidedly Mediterranean or even Arabic influenced in its inflections. Besides Greece, Lindsay had also been to Turkey and worked with Syrian refugees, which might explain the Arabic tones.

However, Lindsay and her mother both explained it away as a result of learning a bunch of languages at once. If you ask us though, it seemed like the result of Lindsay trying to fit in with a culture (and billionaire) she admired. Having spent a lot of time in Europe the past few years, she's likely comparing herself to the people there and reaching for a level of sophistication she's always been lacking. Whatever the reason, it's still pretty weird even for Lindsay.

1 Converting to Islam... maybe?

Via: glamourpk.com

Has Lindsay Lohan converted to Islam? It's been a question on everyone's mind for the past year as Lindsay has shown signs of possibly turning to the Muslim faith. In 2016, she was spotted carrying the Qu'ran before her visit with Syrian refugees in Turkey. According to LiLo, “My very close friends, who have been there for me a lot, in London are Saudi and they gave me the Qu’ran and I brought it to New York because I was learning,” she told a Turkish TV show.

She had also been seen wearing a headscarf and even something called a burkini in Thailand, which looks like a cross between a headscarf and a wetsuit. Lindsay also deleted all the photos off her Instagram after her visit to Turkey and since then, they've mostly been about her career and activism. It's possible that the religion of peace was exactly what the former child star needed in order to straighten herself out. If it's true, then more power to her. Alaikum salam, Lindsay.

sources: breitbart.combuzzfeed.comcnn.com, dlisted.com, eonline.com, gawker.com, glamourpk.comla.curbed.comnytimes.comperezhilton.com, radaronline.comtelegraph.co.ukwashingtonpost.com

More in Pop Culture