Very Intriguing Person
is a series about people who fascinate us, for better or worse.
Every other day it seems I’m confronted with pictures of Lindsay Lohan in my Instagram Explore feed, whether she’s sandwiched between Paris Hilton and Britney Spears on a night out, passed out drunk in a car, or posing sexily with kitchen knives in a racy DIY photo shoot. The accounts updating me on Lohan’s party girl past are usually Y2K fan pages dedicated to all the trashy exploits of our Juicy-wearing faves from the early ’00s. Captions like “lindsay lohan is always a mood” and “My spirit animal. 💫” meme-ify these images of her with eyes half-shut and a lit cigarette dangling from unlatched lips, as though she’s the messy patron saint we can look to late on a Sunday evening when reality of another week gone by sets in, and the best way to level with any regrets is by staring at a picture of her crying in court about to get handed another probation violation and muttering to ourselves, “same.”
Because millennials witnessed rapid technological change at such an early age, we’ve developed a real knack for clinging to the slivers of a life remembered before everyone was connected, all of the time. It's made this generation one of the most nostalgic, openly longing for ten and 15 years ago (and sometimes even 20) through fashion, throwback accounts, musical influences, BuzzFeed listicles, etc. And so celebrities from the late ‘90s and early ’00s whose careers flourished before fizzling out have a second life by nature of existing. The exploits of faded Y2K celebrities are leveraged by nostalgic fans as #relatablecontent — Paris Hilton’s lip gloss-covered cold sore, Britney’s bald moment, Lohan crashing Samantha Ronson’s Mercedes, all of it a big mood to someone out there. If you were just old enough to hear about them on MTV and in the headlines dotting the gossip rags in the grocery store checkout aisle, these hedonistic Hollywood stories stick in your memory like fairy tales.
There are many more of these fallen stars who keep puttering along, relying largely on this nostalgia factor. Spencer Pratt and Heidi Montag have signed up for a Hills reboot; Macaulay Culkin recently reprised his Home Alone character at the tender age of 38 for a Google Assistant ad. Lohan, however, has bigger things in mind. She’s lent her name to three nightclubs in Greece, one in the capital Athens, one on the island of Rhodes, and one on the island of Mykonos. The latter is the subject of a new MTV reality show which chronicles the trials and tribulations of Lohan trying to “build her brand” with the help of a crew of influencers she flies in from the US. After three semi-reclusive years living in Dubai, where paparazzi are illegal, Lohan is now taking the familiar narrative — the addiction, the daddy issues, the disturbing behavior — and shoving it into a new, unlikely identity: boss lady.
“Like, people have to just let go of [my past] and stop bringing it up because it’s not — it’s gone,” she said in a June interview with The New York Times. “It’s dead. And that’s the most important thing to me.” The irony, of course, is that Lohan is continuously confronted with this past as she forges her new path because, without it, it’s likely no one would be calling for interviews or tuning into the show to see how she’s looking nowadays. Lohan was a party girl, but she was also a legitimate burgeoning star, which made her fall from grace so fascinating and confusing. Her early movies like The Parent Trap and Freaky Friday captured the hearts of kids and tweens everywhere, and when the time came for her to shed her Disney roots she walked into Tina Fey’s Mean Girls, one of the defining millennial comedies. Her charm and dramatic ability superseded her increasingly reckless reputation; even at the height of her partying phase in 2006, she was still cast alongside Meryl Streep and Lily Tomlin in Robert Altman’s A Prarie Home Companion.
Now, she relies on memories she loathes to leverage a new identity meant to be the very antithesis of her old reputation, even though it still revolves around partying. On paper, it shouldn’t be a problem; Kim Kardashian, after all, rose to fame with a sex tape and is now heralded as a makeup and tech mogul. But Lohan’s trajectory isn’t that simple, the alarming behavior that’s dogged her entire time in the public eye is never far behind, and it’s going to take a lot more than a nameplate necklace that reads “boss” to erase it. It’s been less than a year, for instance, since the Instagram Live video showing her trying to steal two homeless boys she assumed to be Syrian refugees away from their parents on the streets of Russia.
The very idea for Lohan Beach House Mykonos was born out of tragedy. On her 30th birthday, she was at the beach where the club now stands with her abusive ex-fiance Egor Tarabasov, who allegedly assaulted her. “Instead of crying or getting angry, I said I'm going to own this beach one day because I always want everyone to feel safe,” she said in the show. As a made-for-TV Boss, Lohan comes off as a hardened, no-nonsense, downright tyrannical businesswoman. But enmeshed in all of this is the sense of empowerment that was never allowed her as an unprotected young girl in the spotlight.
It’s here that I lay down my defenses against cheap nostalgia, look at this LiLo phase, and mutter “mood” to myself. Her urge to use success as a way to erase anything shameful or bad that might have happened in her past is a coping mechanism I’ve fall back on, as if achievement — and not tedious emotional weeding — will have the power to reach back and right every wrong.
Despite her support of Harvey Weinstein, the aforementioned kidnapping attempt, and the rest of her problematic history, the old Lindsay still summons loyalty from her followers, even as the show has been panned. “kinda happy someone I kinda grew up on pace with made it through the child-star gauntlet without dying before 30 or ending up dumpster-diving, etc.,” reads one YouTube comment, on a video of her doing an interview with Radio host Sway Calloway. I understand this protective instinct. Even though she’s been personally responsible for a lot of bad things, I still want to believe she is a victim deserving of another chance. When Lohan was young and going through it, the lack of empathy people showed her was kind of astounding. (One example: A 2004 interview with Howard Stern where Donald Trump said of a then 18-year-old Lohan, "She's probably deeply troubled and therefore great in bed.”) Going along with her tacky ploy for D-list stability now seems almost like a passive righting of those wrongs.
“We have a business to run, so there’s no emotion. The second you become emotional I’m going to become Putin,” Lohan says to business partner Panos Spentzos in the first episode, while making a chopping motion across her neck. The vulnerability wielded against her when she was young is gone, leaving an emotionless, money-driven brand-mother prepared to fire and flay anyone who stands in her way. Just like the hard-partying, this is another extreme way of coping. Speaking recently in an interview with Entertainment Weekly on the experience of being the boss of her young club ambassadors she said, “I was able to watch as an overseer and really understand. Was I ever like that? Maybe. But this can’t happen now…. Work is work, and I don’t want any mucking about.”
Her promotional quotes all sound like this, as if repeating the attributes of her new bossed-up identity enough times will eventually convince us they are true. But every casual scroll that leads us to an infamous pap shot of Lohan tells a contrasting story, one more familiar — and sometimes, more relatable — than the polished LiLo she wants us to see. The past may be dead, in her mind, but it remains extraordinarily present to all of us scrolling through the feed.
Correction: An earlier version of this piece mistakenly stated the date of Lohan’s abduction attempt.