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.

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.

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.

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.

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.

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."

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."

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.