Linday Lohan credit: Bill Davila/FilmMagic; Headshot: Tucker Leary; Design: Maitane Romagosa/Thrillist
After scrolling through more than 700 pages of Getty photos featuring Lindsay Lohan, one learns a few things. She is a beautiful chameleon, regardless of hair color or decade of cringe fashion. She has exactly two go-to paparazzi poses, the peace sign and blowing a little kiss. She has volcanic chemistry with every single woman alive and almost none with men, which, when you reflect on her misunderstood past, makes a whole lot of sense.
“Lindsay Lohan was the official Trojan horse of female queerness,” Jill Gutowitz writes in her new book Girls Can Kiss Now. “We loved her so much and for so long, and then, when no one was looking, BAM, she hit us with That Gay Shit”—specifically referencing her relationship with Samantha Ronson, hot girl DJ, in the mid-aughts that made for years of a paparazzi field day and was practically weaponized to sucker punch her infamous downfall.
In Girls Can Kiss Now, Gutowitz blends queer and, specifically, lesbian pop-culture analysis from the ’90s until the present and hilarious, heartfelt memoir about growing up closeted, gawping at many of said Getty photos as a teen, before coming out largely thanks to Orange Is the New Black. “That blew open my world and knowledge of queerness,” she said chatting with Thrillist last week. In mapping out “all of these chapters of queerness in media,” Gutowitz devotes a chapter to Lindsay, Samantha, and other celebrities who were chum for the toxic tabloid culture of the ’00s. And while people like Britney Spears and Amanda Bynes have finally and righteously course-corrected their images stained by a rabid blogosphere, Lindsay Lohan hasn’t been granted the same reprieve from the ways that we as a society mistreated her. How did we get it so wrong?
With the recent news that Lohan is making two movies with Netflix, it felt like the perfect opportunity to revisit her career, reevaluating the many gifts she has given us, from Life Size to Lindsay Lohan’s Beach Club, and the queer signaling hiding in plain sight throughout the years. Gutowitz, a notable Lohan lover, gamely walked through some extremely cherry-picked moments from the many eras of Lindsay Lohan Getty photos where we concluded several things: Lindsay Lohan is so hot, Lindsay Lohan is so talented, and Lindsay Lohan deserves so much better.
This interview has been edited and condensed.
2000: The cool kid era
After her breakout role in the 1998 remake of The Parent Trap, Lohan starred in the made-for-TV movies Life Size (2000) opposite Tyra Banks and Disney Channel’s Get a Clue (2002).
Lindsay Lohan, in my mind, has always been the cool girl. She was exactly what I wanted to be at each age growing up, which was a little bit femme, but also a little bit tomboy and chill vibes. It’s so funny what movies that you see a million times do to your brain because I see this photo now as a 30-year-old and I still think she’s older than me and cooler than me. I still look at this image of her in Life Size in the year 2000, and I’m just like, “That is what I want to look like when I grow up.” I do feel very influenced by her look, her relaxed, flat, straight hair, her casual striped tees—can’t get enough of casual striped tees.
And maybe there was something a little bit, not queer about her relationship with her and Tyra Banks, but there was this maternal energy that I was very drawn to. I used to love big sister stuff where somebody has a really cool, a little bit older female idol.
2003: The Freaky Friday era
Lohan kills it in yet another remake, Freaky Friday, with Jamie Lee Curtis, beginning the transition from child actor to teen superstar.
I know that we already know this, but Gen Z teens owe literally everything they have to Lindsay Lohan’s image in Freaky Friday. She is the blueprint. All of the chunky highlights, the tiger stripe stuff that’s coming back. I think I’ve said this on Twitter before that her band Pink Slip—they are Muna. We queer millennials, we actually had Muna before we knew that we had Muna.
My next era where I wanted to be Lindsay Lohan was in high school and being a little edgy and being like, “Mom, you just don’t get me, I’m an artist!” And there was such a big moment when I was in late middle school, early high school for emo music, pop-rock girl music. I’ve watched Freaky Friday so many times, even in the last five years, and it just holds up so well. This is one of the best movies of our time.
Again, I feel like she was, without intentionally, signaling queerness in a way in this movie that really resonated with me. Everything I just said: the pop-punk girl, “I hate you mom, even though you’re honestly lovely and take really good care of me.” I mean, do we even need to get into the hot Jamie Lee Curtis of it all?
2004: The Mean Girls era
Mean Girls came out in April 2004, immediately catapulting Lohan into the upper stratosphere of celebrity where the paparazzi begin tailing her and she appears on MTV’s Total Request Live many, many times.
This is so lesbian, handing boxes of PlayStation games to other women. Especially in this era, when she was doing all this TRL stuff and MTV’s Spring Break and dancing in a bikini with Sisqó on a beach, she was very much positioned as the girl that every girl wants to be and the girl that every guy wants to hook up with. I think when she started dating Samantha Ronson and there were all these photos, it was so much more powerful because she wasn’t some random girl with one song on the radio. She was the star of the moment who was very much positioned as the apple of every boy’s eye and she was dating a hot masculine-presenting woman. It was so cool.
She also probably received so much disgusting attention from men, because she was birthed into the world in this era of a Disney child star who then became very sexy and marketed towards men. She probably was extremely uncomfortable all the time with men, because even if they weren’t being creepy, it had probably happened to her so many times that she had her guard up, you know? And look how in her power she is here.
Also this outfit, the cool band T-shirt with an odd choice, honestly, a net vest? It does feel like she like put on a T-shirt and someone on her team was like, “Add something girly,” and she was like, “All right.”
2004: The “please don’t look at me” era
Lohan released her debut studio album Speak in September 2004 and clearly hates all the attention she’s been getting post-Mean Girls.
“Can you please respect my privacy,” as the old adage goes? I love how so many 2000s music videos had this futuristic tech robot apocalypse vibe. At this point, Lindsay Lohan has become the It-girl and so mainstream that she has received so much attention and scary negative Britney Spears-like attention already that she has in this short amount of time already felt like she needed to put out a music video saying “never perceive me.” And in doing so, also coming out as a hot girl.
In some ways, I feel like I remember this entire video, but I almost really only remember its blue/gray color scheme because I was probably shame staring at the floor the whole time. I was like, “You guys, we should really respect her privacy and none of us should look at her.” Don’t look at her. I’m not. Why are you?
2005: The onset of the gay era
It would be three years before Lohan would admit to her relationship with Samantha Ronson, but here, in 2005, at the Teen People Young Hollywood issue release party, it’s clear the two share a special chemistry.
It’s Samantha Ronson with a cigarette. Here, she’s wearing a loose tie, which is cool. In other ones, she’s wearing a loose vest and a fedora—also sick for that era. I obviously feel nostalgia for a lost era, but I also just think this is a perfect couple. Just this cute femme, “I’m going to play with these, let me spin these little discs,” and her also hot masc girlfriend, loosely smoking a cigarette being like, “Let me help you.” I don’t know if this was the first photo of them, but I think it went downhill from here, unfortunately.
When Samantha and Lindsay started dating, I had not seen a queer relationship amongst or a gay lesbian relationship amongst people that were my age or my peers, and also ones who were really fucking hot. I think there was two parts of it that blew my personal reality open. One being that it was really hot and two being that you can tell in this photo that there’s a connection there. And that there is something like an emotional bond there because my understanding of lesbianism, up until this point was just so, so narrow and I also never thought of it as being at all about love and connection. So I feel like this is an educational photograph is what I’m saying. This should be on a dot-gov website.
There’s just a lightness to this, you know? Also with Samantha Ronson, it’s like, this could easily be a photo of a man who looks more serious and is telling Lindsay, “This does this, this does this.” Men love to tell people things. You think Lindsay Lohan gives a fuck about what the little knobbie does? No, this is a cool, hot lesbian showing her things. This is real shit. Will I write 40 pages of fanfic about this? Yes, I will. I desperately want to make the prestige limited series called Lindsay and Samantha that’s very “justice for Lindsay and Samantha” and shows how fucked it was for them in this moment. Nobody steal this from me. This is mine. Call me, Showtime specifically because I feel like they’re the most lesbian network.
2010: The fallen Hollywood starlet era
By 2016, a victim of the Perez Hilton-esque gossip-driven blogosphere, Lohan was pegged as a “party girl” alongside other tabloid favorites Paris Hilton, Nicole Richie, and Britney Spears. In 2007, she was arrested for a DUI, the beginning of her “downfall” in the public eye.
The metaphors here couldn’t be hit harder. This is a woman so desperate to say how she’s really feeling and cannot do it at all. There’s a tiny, tiny, tiny voice in her that is crawling to come out and just wants to say “fuck you” to the world. And here we are with this Getty image, extremely zoomed in. She put this on her little fingernail because it’s all she had. I can see so much pain, so much angst in this photo, and I’m also like, she’s beautiful. She’s so stunning. Why did we do this to her?
Immediately following the Samantha Ronson era, so much of her addiction and legal issues got not just grouped in with, but almost completely blamed on her queerness and her relationship. Which was so unfair because I felt like I was getting to watch this great thing blossom, and then—I mean, obviously, they became messy and toxic and obviously not right for each other. But it was still this really fun, exciting thing to witness as a closeted queer teen. Then she was not well, we were not good to her and all actively made it worse by participating in the tabloid frenzy about it. But then it all got blamed on Samantha Ronson, or that she was an addict, she’s crazy, she’s gay, and she needed help. She was not crazy. She was gay. None of these are bad things. It was all written off as being “she is bad now.”
2016: The first attempted resurrection era
Lohan wasn’t probation-free until 2015, after several arrests and many documented issues with substance and alcohol abuse. In 2016, she’s out in the world trying to rehab her image, and delivers this surely coded look.
I feel like she sees a lot of herself in Harley Quinn. She’s not only canonically bisexual, but is a misrepresented villain, and really, she’s just a girl with feelings. Gay feelings. Let her be Harley. Good for her.
Lohan traveled widely during this time, jumping around London, Dubai, and elsewhere, and, thanks once again to Perez Hilton, is made into a bizarre punchline when she fluctuates accents in interviews.
It’s performance art to me. She brought me so much unbridled joy as a kid that I think I started turning my head away and was like, “You know what, I’m actually not going to even listen to this. She can have her little fake accents if she wants. If she’s British, good for her. I won’t participate. I can’t look it directly in the eye.”
Perez Hilton, more than anyone, blew her queer relationship and battle with addiction and everything so out of proportion and painted it as so negative. “Wild child,” “starlet gone wrong.” He suffered almost no consequences at the time, especially being that he won that libel lawsuit with Samantha Ronson and she had to pay him money, which is awful. Here in 2016, he’s trying to do what a high school bully does looking at a yearbook, you know what I mean? He’s like, “Come on, you guys, we still fucking hate her, right?” And we’re like, “No, we hate you.”
2019: The brief Mykonos era
Lohan buys a club in Greece and MTV premieres its own Vanderpump Rules knockoffcalled Lindsay Lohan’s Beach Club.
I’m going to go out on a limb here and say that her two poses are actually like the two genders. I feel like as a bisexual, she has these two moods. One, which is the peace sign, absolutely pandering towards queer women, and the other, blowing a kiss, is absolutely leaning into the femme male gaze, the Marilyn Monroe of it all. So for me, this makes sense that she’s leaning into the camp femininity, posing with a bunch of drag queens. But I do feel like—and I’m projecting certainly here—her in her natural state is throwing up a peace sign.
I’ve seen the Mykonos video, the hair flip. I still very much love the internet culture surrounding her, but I actually have not watched the Beach Club, which is devastating. I really want to, I just I think it was another thing when she started devolving in the public eye. I just was like, “I don’t want it. I’m preserving this.”
2022: The second comeback era
Fast forward to the present day and Lohan is making not one, but at least two movies. She’s back, baby!
This man is Chord Overstreet, which I only know from Glee, which I also only watched because I was gay. So he’s gay collateral, you know what I mean? But yeah, I will be streaming this movie, absolutely. This, to me, is the most important Christmas movie since Happiest Season. It is clearly going to be painfully heterosexual, but she is canonically bisexual, which means that it’s a queer movie. That’s how I can get myself to watch it.
She signed a two-movie deal with Netflix. I’m so happy for her. I want her to be in the public eye again in a way that feels good and safe. I want her to be in movies again. I think that she’s an amazing actress. She wasn’t as popular as she was because she was just hot. She was an amazing comedic actress. She can do a Mean Girls or an Easy A kind of vibe. She can do that shit in her sleep.
I re-watched Parent Trap recently. She was so ahead of her time and probably smarter than anyone around her at truly 12 years old. I feel the stuff that she went through rocks you in a way that I don’t know if somebody like her or like Britney can come back from. I hope that Lindsay can lead a healthy life still because I genuinely love her so much. I know she still has it in her. Let’s fucking go. But, yeah, I will be streaming her Netflix movies, including Falling for Christmas (2022).
Leanne Butkovic is a senior entertainment editor at Thrillist.