Lindsay Lohan's Sketchiest Moments

This feature references substance misuse and allegations of sexual assault. 

Lindsay Lohan's journey from cute Disney kid to comeback kid in the 2022 movie "Falling for Christmas" has been littered with messes of her own making. But while "The Parent Trap" star failed to dodge many of the common pitfalls of child fame — such as spending her teen years partying like a rock star — she's never simply given up and faded into obscurity. After her career peaked with "Mean Girls" in 2004, LiLo dabbled in fashion, launching her own leggings line in 2008. She also tried channeling her inner Lisa Vanderpump for the 2019 MTV reality series "Lindsay Lohan's Beach Club." But the show lasted just one season.

While she might be impressively resilient, Lohan built herself a bad reputation as she burned bridges with Hollywood producers and careened through L.A.'s nightclub scene, occasionally finding herself in trouble with the law. In 2009, she complained to Interview about why she thought she wasn't getting the job offers she wanted, lamenting, "People are so distracted by the mess that I created in my life." But in the opinion of fellow party girl Tara Reid, Lohan had it good. "I just don't think that people should get away with that much," the "American Pie" actor told TMZ in 2013. "... I think this girl gets chance after chance after chance after chance." Because of this, Reid predicted that Lohan would eventually clean up her act. But as Lindsay Lohan's sketchiest moments show, for a long time, the star just couldn't stop trying to make sketch happen.

In 2013, Lindsay Lohan was seemingly in need of some guidance in her life when her plight caught the attention of the ultimate life coach, Oprah Winfrey. For "Lindsay," a docuseries that aired on Winfrey's network OWN, the talk show icon doled out a little tough love, telling the troubled star, "You need to cut the bulls***." The exchange followed the crew's allegations that Lohan had been acting unprofessionally and delayed the production. During the series finale of "Lindsay," the star made the heartbreaking confession that she'd experienced a miscarriage during filming, per Us Weekly. 

However, an insider alleged to Radar that Lohan had lied about the loss in a purported bid to appear more sympathetic. "This is what Lindsay does. She lies! Her family and friends had no clue about her 'pregnancy' and subsequent miscarriage," the source claimed. Lohan shared the miscarriage story again amid her legal battle with the manufacturer of her line of leggings but refused to testify about it under oath, per TMZ. 

Then, in 2016, Lohan tweeted the words, "I am pregnant!" while referencing her 2009 movie "Labor Pains" (via People). Her father, Michael Lohan, claimed that she had texted him to say she was expecting. However, a source told Page Six, "She is saying she is pregnant, but it could be for attention." Thankfully, when Lohan made a pregnancy announcement in 2023, she was finally in a good enough place that no one questioned it.

While discussing "Mean Girls" with ABC News in 2004, Lindsay Lohan suggested that she was too mature to behave like The Plastics, the cruel high school clique who inspired the movie's title. "Girls like the drama," she said. "... But then when you get older it's kind of a hassle." Or it's just a weeknight in LiLo's world. Two years later, an eyewitness told Gawker that she saw Lohan use a bathroom wall like a "Burn Book" page. The actor was lurking in the ladies' room at the NYC hotspot the Dark Room when she reportedly borrowed a permanent marker from a fellow patron and scribbled, "Scarlett is a bloody c***."

The target of her graffiti was presumably "Black Widow" star, Scarlett Johansson — and she was surprised that LiLo went so low. Especially since she had no idea why she inspired such intense feelings of animosity in the other actor. Recalling the incident in 2008, Johansson told Allure (via the New York Post), "I remember it was something really vulgar — I mean shockingly so, like, 'Whoa, what, who are you?'"

Lohan had previously confessed that she found comparisons of her career to those of Johansson and Keira Knightley frustrating. "Their fan base is more mature and my fan base is younger," she told the Los Angeles Times in 2005. "So [the media is] writing about me going out all the time." Allowing fellow clubgoers to watch you create vulgar graffiti is another surefire way to make headlines.

In 2011, Charlie Sheen went on a media rampage. The raging warlock fueled by tiger blood blasted Chuck Lorre, the creator of his hit series "Two and a Half Men," in an open letter published by TMZ. "This contaminated little maggot can't handle my power," it read in part. "Clearly I have defeated this earthworm with my words — imagine what I would have done with my fire-breathing fists." At the time, it was hard to imagine that anyone could create a situation wherein people felt any sympathy for Sheen — enter Lindsay Lohan, stage right.

In 2012, she boasted an overdue tax bill of upwards of $200,000, per Reuters. However, Lohan and Sheen had become friendly while filming "Scary Movie 5," and in an extraordinary act of generosity, he gave his new pal $100,000 to help her get out of debt to Uncle Sam. In an interview with ET, Sheen revealed that Lohan didn't seem very grateful for the gift. "I'm still waiting for a text to say 'thank you,'" he said. "Anything, you know?" He regardless added that he was still rooting for her.

After getting called out by the guy who managed to get himself fired from one of television's most lucrative gigs in history, Lohan sent Sheen a floral bouquet and card, per TMZ. Sources blamed the delayed acknowledgment of Sheen's gift on a broken phone and Lohan's many legal woes that were keeping her preoccupied at the time.

Before she announced that she was working on her own makeup line, Lindsay Lohan tried to convince fellow former child star Ariana Grande to cut back on her cosmetics usage. In 2016, the Art of Shade Instagram account noticed that Lohan left the same comment on three of Grande's Instagram photos — "Too much makeup." The beauty look that Lohan clearly didn't like consisted of winged eyeliner, bubblegum pink eyeshadow, and coordinating lipstick.

The actor's unsolicited beauty advice apparently didn't make Grande less of a "Mean Girls" fan. In 2018, she paid homage to Lohan's magnum opus by recreating scenes from the movie in her "Thank U, Next" music video. Grande cast herself in the role of Plastics queen bee Regina George, while her former "Victorious" co-star Elizabeth Gillies played Lohan's character, Cady Heron. Lohan shared her thoughts on the video in a since-deleted Instagram post, writing, "Ain't nobody Lindsay Lohan like the real Lindsay Lohan. But so flattered by [Ariana Grande] loving ["Mean Girls"] so much!" 

On "The Jenny McCarthy Show," Lohan shared her theory on why the real deal didn't get asked to make a cameo in the video, saying, "They probably couldn't get in touch with me, I guess." But director Hannah Lux Davis later told Cosmopolitan, "[Grande] was really adamant about her friends being so prominent in the video." Instead of critiquing Grande's makeup, maybe Lohan should have been trying to pull a Cady by infiltrating the younger pop star's friend group.

In 2017, it looked like maybe Lindsay Lohan was entering her Angelina Jolie era by taking an interest in the plight of refugees. On Instagram, she revealed that she'd even met with Turkish President Recep Tayyip Erdoğan to discuss how he was helping Syrian refugees. But the following year, her concern took a dark turn while she was in Moscow.

In an Instagram Live video shared by TMZ, Lohan is exiting a vehicle as she says, "I just want to show you a family I met, a Syrian refugee family." She then approaches a couple and two young boys sitting on the side of the road. At first, she says she wants to help them, but then she accuses the adults of being child traffickers. "I won't leave until I take you," she says to the kids as she follows the fleeing family. After she asks the parents if one of the boys is their son, their presumably frightened mother decides that she's had enough of the harassment and hits Lohan. "I'm so in shock right now," Lohan tearfully says. "I'm just so scared."

Earlier in 2018, Lohan had told W magazine that things were looking up for her since she'd moved to Dubai, where she was working on various business ventures. But after the Instagram video hit the web, a source told People, "Lindsay hasn't changed whatsoever ... She's a nightmare to those around her."

If Lindsay Lohan's fingers are as sticky as some stories suggest, she would have found herself right at home among the members of the Bling Ring, the thieves who stole luxury goods from people celebs like herself and her frenemy Paris Hilton. In 2011, Lohan pleaded no contest to the theft of a $2,500 necklace from a jewelry store. As punishment, she received another piece of jewelry — an ankle bracelet — and served her 35-day sentence under house arrest. A judge later chastised her for partying while doing her time, per People.

Model Lauren Hastings had previously told Buzznet (via Inside Edition) that Lohan had stolen multiple items of clothing from her home during a house party in 2007. However, the L.A. D.A.'s office found that there wasn't enough evidence to prove her claims, and Lohan apparently denied the allegations. The following year, Lohan was accused of slinking off with a fellow clubgoer's pricey mink coat, per CBS News. No charges were filed against her because it was returned.

Then, while Lohan was playing late screen legend Elizabeth Taylor in "Liz & Dick," she allegedly set her sights on obtaining a bracelet Taylor had gifted to her nurse. While filming the 2012 TV movie, an insider alleged to Radar that the bracelet mysteriously vanished on the same day that Lohan visited the nurse's home. The jewelry reportedly found its way back into the nurse's possession via Lindsay's team when there was talk of getting the authorities involved.

Celebs living out their Disney princess dreams best be prepared to face the evil stepmother energy of a disgruntled Lindsay Lohan. In a 2019 interview with Variety, the former Disney star confirmed that one of her biggest dream roles was that of fellow redhead Ariel in Disney's "The Little Mermaid." 

Actor Halle Bailey would later nab the part in the live-action remake of the animated film, but there was another big opportunity to play Ariel available — the 2019 Hollywood Bowl live concert performance of "The Little Mermaid." Unfortunately for Lohan, she wasn't invited to be a part of that world, and it was "Glee" star Lea Michele who got to jam with a cool crustacean band. In response to an Instagram post about the news of Michele's casting, Lohan simply wrote, "Huh?" Michele reacted to being the recipient of some salty LiLo shade on "Watch What Happens Live," saying, "I find it to be an honor, truly ... It's classic! ... It's great."

The "Freaky Friday" star also wasn't impressed with the Cinderella-inspired dress that her fellow former Disney darling Zendaya wore to the 2019 Met Gala. When Lohan saw the look on Instagram, she wrote (via Seventeen), "Claire Danes did that with [designer Zac Posen] already." Apparently, she didn't feel like this remark was shady enough because she added, "[Claire Danes], you wore this dress so beautifully. I don't know why someone thinks that they can be more chic. Ever." Bibbidi-bobbidi-burn?

In 2006, Pluto was downgraded from a planet to a "dwarf planet." But that same year, three stars collided to give us the universe's most important photo. However, Paris Hilton would later say that the visual representation of that chapter in pop culture history — a pic of Hilton, Lindsay Lohan, and Britney Spears squeezed together in a car — was not what it seemed. 

In "Paris: The Memoir," she reveals that she didn't invite Lohan to hop into the vehicle with her and Spears when they were all leaving the same party. They weren't on the best terms at the time, in part because Lohan had made what Hilton said was a false accusation about her. "She said that I hit her elbow and dumped a drink on her," Hilton recalled (via Vanity Fair). The socialite-turned-entrepreneur also opened up about the moment on her "This is Paris" podcast, saying, "It was kind of awkward because, at this point, we were just having some drama."

Apparently, Lohan engaged in other behavior that made it impossible for her and Hilton to be as friendly as they looked in that iconic image. "Back in the day we were actually close friends, and then she did a couple of things that really hurt me and just betrayed my trust, and caused a lot of drama," Hilton explained. It probably didn't help matters that Lohan was captured on camera calling her a sexist slur.

Late singer Aaron Carter was the source of Lindsay Lohan's feud with "Lizzie Maguire" star Hilary Duff. In a 2005 appearance on "The Big Idea with Donny Deutsch" (via Contact Music), Carter admitted that he decided to date Lohan when he started to find his relationship with Duff rather dull. "Then I didn't want to do that anymore, so I got back with Hilary," he said. After their romantic conflict escalated, Lohan poked fun at it while hosting "Saturday Night Live" in 2004. However, Duff wasn't laughing. "I think it's really mean when they make fun of people. If I ever hosted 'SNL,' I wouldn't do a skit about her," she told USA Today.

In 2008, Duff told Allure (via People), that Lohan was the only one fixated on the situation and expressed frustration over her refusal to stop bringing it up. "She was talking about it and I wasn't. It made us both look bad and put up a big weirdness," Duff explained. Tina Fey confirmed that Lohan gossiped about the feud while they were filming "Mean Girls" together, telling Entertainment Weekly, "She tried to explain to Amy [Poehler] and me her beef with Hilary Duff, but we couldn't crack it. But we were pretending we could follow it." 

By 2007, Lohan had finally moved on. Speaking to People about their relationship, Duff said, "We were hanging out the other night and she's a nice girl."

2012 was a rough year for Lindsay Lohan. That November, she was arrested after punching a woman in the head at a Manhattan club, per the New York Post. She then found herself in more legal trouble in California when prosecutors charged her with lying to a police officer about a car crash she'd been involved in. Lindsay claimed that she wasn't the one behind the wheel when she was actually alleged to have been responsible for the wreck, per TMZ.

A month earlier, Lindsay had lied to her dad, Michael Lohan, about her mom, Dina Lohan, doing drugs. TMZ published a recording of Lindsay allegedly saying, "Dad, she's on cocaine." Lindsay later added, "She's like the f***ing devil right now." The frantic phone call took place while Lindsay and Dina were fighting in the wee hours of the morning. They'd been partying together in NYC, and a war of words apparently escalated into a physical altercation, per TMZ.

Lohan later confessed that she'd told her father a falsehood in the heat of the moment. "My mom does not do cocaine, clearly. And that's a fact," she told TMZ (via E! News). While the lie was hurtful, her mom forgave her and applauded Lindsay for taking some accountability for her bad behavior. "I'm so proud of her for telling the truth because it destroyed me," Dina told ET. "I mean, I cried for weeks. It just hurt me so bad and she knew how horrible that was."

In 2019, Lindsay Lohan was a judge on "The Masked Singer Australia." The job required her to guess the identities of Aussie celebs as they belted out tunes from behind elaborate masks, but because the American star's knowledge of pop culture in the Land Down Under was basically nil, she had a tough go of it. Her fellow judge, Dannii Minogue, confirmed to The Daily Telegraph that Lindsay had no clue who some of the entertainers were even after they were unmasked.

But one contestant she immediately recognized when she saw his face was singer Cody Simpson. She'd previously guessed that he was her ex, Aaron Carter, but Simpson had actually dated a different Lohan — Lindsay's younger sister, Ali Lohan. Because of the relationship, Lindsay's social media behavior was not that of a consummate professional when Simpson won the show. She posted a quickly-deleted Instagram photo of Ali and Cody together and captioned it, "When you realize you failed. And you settle for less [Cody Simpson]. Family is everything. You won the masked singer but you lost on your future." At the time, Simpson was dating Miley Cyrus, so this certainly seemed like a dig at them both.

On the show, Lindsay also told him, "I want my furniture back because I bought the furniture for your house in Venice." But Simpson later told Punkee that he and Ali never received the items that Lindsay supposedly ordered for them. 

Lindsay Lohan's community service for stealing a necklace included a job that was clearly meant to scare her straight — working at the Los Angeles County morgue. The assistant chief coroner said that she would be performing janitorial duties. But in a 2014 interview with The Telegraph, Lohan claimed that what she was doing during her long hours in the morgue was far more traumatic. She also suggested that she was given the macabre job because of who she was. "It's different for me than it would be for other people — like, no one would really have to work at the morgue in L.A. and roll a body bag for Whitney Houston," she said. Yup, she appeared to claim that she handled the body of the late music icon, who died in February 2012.

Alas, TMZ reached out to the coroner's office and learned that this did not happen. An official said that Houston was never placed inside a body bag and that Lohan didn't touch her body. The only bags the "Life-Size" star likely touched were of the garbage variety, as taking out the trash was listed as one of her less-headline-grabbing duties. Other potential tasks she was possibly ordered to perform were cleaning the restrooms and floors. Ahead of her first day on the job, the assistant chief coroner told People, "She won't be handling any dead bodies but she'll certainly see them."

In October 2017, The New York Times published its bombshell report about Hollywood producer Harvey Weinstein's long history of sexual harassment and assault. Multiple women came forward to share their stories, including actor Ashley Judd. Mira Sorvino, Asia Argento, and Rosanna Arquette were among those who spoke to The New Yorker contributor Ronan Farrow about their own traumatizing experiences with Weinstein, and soon, other stars rallied behind the alleged victims (he denied the allegations). In a statement to HuffPost, Meryl Streep applauded their bravery and wrote, "The behavior is inexcusable, but the abuse of power familiar." And in her statement to Variety, Jennifer Lawrence said, "This kind of abuse is inexcusable and absolutely upsetting."

Lindsay Lohan also decided to speak out, but her first instinct was not to express support for Weinstein's accusers. Instead, Lohan recorded an Instagram video in which she defended the movie mogul by saying that she, personally, never had any negative experiences working with him. "I feel very bad for Harvey Weinstein right now. I don't think it's right what's going on," she said. Lohan also encouraged Weinstein's wife at the time, designer Georgina Chapman, to speak up in his defense. Instead, Chapman told People in a statement that she was divorcing the producer.

Lohan also said of Weinstein's accusers, "I think everyone needs to stop. I think it's wrong. So, stand up." But his victims didn't stop speaking out, and now Weinstein is spending his final years in prison.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

The Chateau Marmont has been a Hollywood institution since 1929. The famed hotel is associated with glamour, excess, mystique, and the reckless abandon of the rock stars who've raised hell there. Some of the entertainment industry's biggest movie stars have sought secrecy or frivolity underneath its roof, including Marilyn Monroe and Elizabeth Taylor. Lindsay Lohan channeled the former for a New York magazine photoshoot and portrayed the latter in the movie "Liz & Dick" — and she also discovered the allure of the Chateau Marmont. In fact, she was shooting "Liz & Dick" when she resided there in 2012.

During her 47-day stay, Lohan spent $3,145.07 on minibar items and $686 on cigarettes. TMZ obtained a copy of her pages-long bill, which revealed that she owed the hotel over $46,350.04 by the time she was shown the door for not paying any of her expenses when they were due. In his book "The Castle on Sunset: Life, Death, Love, Art, and Scandal at Hollywood's Chateau Marmont" (via Entertainment Weekly), author Shawn Levy explained that Lohan was able to keep getting her credit extended because she assured the hotel that the producers of "Liz & Dick" were going to pay her bill. But this was not true.

While the letter letting LiLo know that her free ride was over indicated that she was no longer welcome at the Chateau, she was photographed there a few weeks after her eviction.

During the filming of the 2007 dramedy "Georgia Rule," Lindsay Lohan's frequent absences earned her a scolding from producer James G. Robinson. The Smoking Gun obtained a copy of a letter from Robinson to Lohan in which he informed her that she was costing the production company boatloads of money. He threatened her with legal action if she didn't get her act together. "Your actions on Georgia Rule have been discourteous, irresponsible, and unprofessional," he wrote. "You have acted like a spoiled child." Sources told E! News that tardiness was an issue when Lohan filmed a cameo for "Glee" in 2012, and Page Six spoke to insiders who said that she tried to get fired from "Scary Movie 5" by saying that she was sick.

And then there was the fraught filming of "The Canyons," as chronicled by The New York Times Magazine in 2013. When Lohan was a no-show two days in a row, director Paul Schrader let her know that her services were no longer needed. But he rehired her when he realized that her replacement just wasn't as talented. Lohan later had to be coaxed out of a closet when it was time to film a sex scene. 

But Lohan doesn't need to be easy to work with to be successful. As media consultant Jenny Hontz told Fox News, "As long as the public is fascinated by her, the Lindsay Lohan brand will probably continue to exist."