Kids today will know of Lindsay Lohan as that celeb who couldn’t guess shit in season one of The Masked Singer Australia, but to Gen Z and millennials, she’ll always be waaay more than that.
From the mischievous twins from The Parent Trap, to the groolest girl in school from Mean Girls, the limit of our love for LiLo does not exist and she can always sit with us (well, almost always…).
Here, I’ve ranked every Lindsay Lohan flicks, from the epic teen flicks that shaped us, to the career-ending flops that you never knew about.
21. The Canyons (2013)
If you take one thing from me, my writing, hell, even PEDESTRIAN.TV itself, let it be this: before you leave this earth, you must read The New York Times’ report about Lindsay’s behaviour on the set of her 2013 film, The Canyons.
Whenever I take a long-haul flight, I load the article on my phone so I can read it in the air as my mid-flight entertainment, and it always kills a solid few hours as I take my time with the lengthy, but incredibly entertaining read.
There’s literally way too much to detail here, such as vanishing from set to bender with Lady Gaga, jumping out of a producer’s car and hauling ass to avoid work, and banging on the director’s door in tears after being sacked (trust me, this is just the tip of the iceberg), plus I wouldn’t wanna ruin the brilliance of the piece by paraphrasing the whole thing.
The film itself bombed as bad as a film can bomb, but her on-set antics were enough to have her yeeted out of Hollywood permanently to the point where still, to this day, her career has not recovered (there’s a reason why she did The Masked Singer… in a foreign country, mind you).
Do yourself a favour and make a cuppa, put your phone on do not disturb, and have a read RN. You will not be disappointed.
20. Among the Shadows (2019)
19. I Know Who Killed Me (2007)
18. Labor Pains (2009)
In this movie that you never knew existed, Lindsay Lohan plays a gal who fakes her pregnancy to avoid getting fired.
17. Till Human Voices Wake Us (2015)
16. Inappropriate Comedy (2013)
15. Liz & Dick (2010)
Just as things were starting to suck for Lindsay’s career, this Liz Taylor biopic was supposed to be her saving grace.
But unlike recent biopics Bohemian Rhapsody and Rocketman, it was a big fat flop.
14. A Prairie Home Companion (2006)
So here’s one I bet ya never knew existed.
Lindsay stars in a musical flick alongside a sick-ass ensemble, featuring Meryl Streep, Kevin Kline, Tommy Lee Jones, Woody Harrelson, Lily Tomlin, and Virginia Madsen.
Not great. But not awful.
13. Scary Movie 5 (2013)
Hate me all ya want, but I’m… not a fan of the Scary Movie franchise.
HOWEVER, I was impressed by Lindsay’s willingness to take the piss out of herself, alongside Charlie Sheen, of all people.
12. Bobby (2006)
11. Chapter 27 (2007)
A must-watch for both Lindsay Lohan and true crime stans, Chapter 27 is a flick about the murder of John Lennon.
It stars a heavily overweight Jared Leto as the killer and Lindsay as Jude, a huge Beatles fan.
10. Machete (2010)
In this hella violent movie, she plays, get this, “a nun with a penchant for guns.”
We love to see it.
9. Herbie: Fully Loaded (2005)
This wholesome AF classic was Lindsay’s last Disney film (bless).
8. Georgia Rule (2007)
Lindsay Lohan, Felicity Huffman and Jane Fonda. Fuck me, what a scandalous line-up.
One of her lesser-rated flicks, what I find most spicy about the movie is the wild behind-the-scenes goss that led to the demise of Lindsay’s career (nowhere NEAR as good as The Canyons tea, but still spicy).
The film was made around the time that LiLo hit the social scene and apparently her “heavy partying” impacted the production of the flick.
Producer James G. Robinson sent a scathing letter reprimanding the actress for her behaviour.
“She missed a day of work without telling anybody and you can have a whole crew and cast standing around — plus the cost of half a million dollars a day lost,” Robinson told CBS News at the time. “The letter served its purpose and she’s a great actress.”
Her behaviour also impacted the culture on-set, according to Fonda, who played Lohan’s grandmother. The legendary actress told David Letterman she had to tell her off “a couple of times” for being late.
“I remember one time I went in the make-up trailer and got mad at her and I said, ‘get on to the set, c’mon we’re waiting for you.’ Apparently she turned to her make-up person and said, ‘Barbarella just yelled at me,'” she recalled.
Also a fun movie, but yeah, the behind-the-scenes goss makes it all the more intriguing, IMO.
7. Get a Clue (2002)
This was the flick that saw our girl transition from child star to tween dream.
In Get a Clue, Lindsay plays Lexy Gold, a teenage high school student who investigates a mystery after one of her teachers goes missing.
6. Confessions of a Teenage Drama Queen (2004)
Here, she plays an aspiring teenage actress whose family moves from the glamorous New York City to the suburban New Jersey.
Spicy fact: This beloved Lohan classic was originally offered to her arch-nemesis, Hilary Duff.
5. Just My Luck (2006)
In this noughties classic, Lindsay portrays Ashley, the luckiest girl in New York City. Why is she the unluckiest girl? Well, ‘cos she loses her luck after kissing Jake (played boy ya boi Chris Pine) at a masquerade bash.
You’d think smewching Chris Pine would be a stroke of good luck, but apparently not!
The movie was written by I. Marlene King, a.k.a. the powerhouse who brought us Pretty Little Liars.
4. Life-Size (2000)
One of her earlier, but lesser known films, Life-Size stars Tyra Banks as a doll, owned by Lindsay’s character, who becomes a human.
It’s so friggen’ cute and wholesome and includes a bunch of stellar quotes, such as the following:
3. Freaky Friday (2003)
I literally love absolutely fucking everything about this movie.
From Lindsay’s co-stars (queen Jamie-Lee Curtis and absolute snacc Chad Michael Murray), to hers and Jamie’s portrayal of one another’s characters to the musical genius of Pink Slip.
Over the Chrissy break I rewatched the flick and lemme tell ya, it’s an instant boost of serotonin. Get on it, fam.
2. The Parent Trap (1998)
LiLo’s first-ever movie is probably her most technically brilliant one ever, not just in terms of the film itself, but also in terms of her acting.
I mean, sure, watching the movie back, that British accent is hardly convincing, but it sure as shit worked on us as wee lil youngsters. Most of ya probs thought it was two different girls, right?
Special shoutout to Elaine Hendrix’s portrayal of Meredith who has become quite the popular character on social media of late.
I will ship every one of you brats off to Switzerland. ???? https://t.co/Gr1SSJmADJ
— Elaine Hendrix (@elaine4animals) June 16, 2018
1. Mean Girls (2004)
And coming in at number one is the film that made fetch happen, Mean Girls.
When I rented the DVD from VideoEzy back in year six, I had no idea that the entire world would still be quoting lines from the movie all these years later.
It’s not just Lindsay’s greatest flick to date, it’s also one of the greatest teen dramas to date and I am certain that one day, when we’re not regular moms, but cool moms, we’ll be telling our kids that if they want some snacks, a condom, or to watch the beloved noughties flick, to lettus know (god love ya!).