Gothamist
A non-profit newsroom, powered by WNYC.
Gothamist
Listen Live
Arts & Entertainment
It's October 3rd, So Let's Talk About Lindsay Lohan
By
Rebecca Fishbein
Published Oct 3, 2014
Modified Oct 3, 2014
Share
FacebookTwitterRedditEmail
Never miss a story
Email address
By submitting your information, you're agreeing to receive communications from New York Public Radio in accordance with our Terms .
By
Rebecca Fishbein
Published Oct 3, 2014
Modified Oct 3, 2014
Share
FacebookTwitterRedditEmail
We rely on your support to make local news available to all
Make your contribution now and help Gothamist thrive in 2026. Donate today
Gothamist is funded by sponsors and member donations
Today is October 3rd, i.e., Mean Girls Appreciation Day, an international holiday that's been observed annually by legions of dedicated Mean Girls fans ever since Aaron Samuels asked Cady Heron what day it was ("It's October 3rd"). That cinematic Millennial masterpiece turned 10 years old this year, making this October 3rd the most significant one yet, save for when it fell on a Wednesday in 2012 ("On Wednesdays, we wear pink!") And in honor of this Holiest of Holy Days, we've decided to make a list of the best roles taken on by one esteemed Lindsay Lohan, a New York native whose epic societal rise and fall was so perfectly sprung by this film to end all films. Note that for the purposes of this list, "best" does not exclude "most cringeworthy," because LiLo is an actress that makes you suffer for her art.
First, a little self-disclosure. I accidentally attended Mean Girls's New York premiere back in the spring of 2004. A few other ninth graders and I went to see 13 Going on 30 at the AMC Loews Lincoln Square 13, and exited the theater to find the main lobby teeming with celebrities—Tina Fey! Rachel Dratch! Sandy Cohen! LiLo arrived last, sweeping in wearing a white dress, heavy makeup and a sneer. We made eye contact (NOTE: Okay fine, we didn't), and from that day forth, I decided she was my Nemesis. Therefore, this list is not impartial, but here it is anyway:
1. Hallie Parker/Annie James in The Parent Trap
This is LiLo's greatest role, and one she should hope everyone remembers her for no matter how many Scary Movie cameos she makes in the future. I still cry every time Hallie sees her mother for the first time, a scene that seems even sadder years after Natasha Richardson's death. And though preteen Lindsay's British accent could have used some work, she did an admirable job portraying both the uptight Annie and cool California chick Hallie—plus, she ensured I would never let anyone pierce my ears at sleepaway camp.
2. Anna Coleman/Tess Coleman in Freaky Friday
LiLo is a woman drawn to dualities, and in this oft-overlooked 2004 film, she admirably emphasizes the personality dichotomy of the Mother/Teen Daughter relationship. The real stars of this film, of course, are Jamie Lee Curtis and Chad Michael Murray's mysterious faux-choker necklace, but it was Lohan's performance as both an angsty teen with ill-advised highlights and an uptight French fry-eating mom that won us over in this post-Parent Trap, pre-Mean Girls world.
3. Cady Heron in Mean Girls
To be honest, LiLo was sort of the weakest link here, with Rachel McAdams, Lizzie Caplan, Daniel Franzese, Tina Fey, Lacey Chabert, Tim Meadows and even Amy Poehler doing more of the heavy lifting. But without Cady, Mean Girls would not exist, just like the limit. And since Mean Girls is the unequivocal greatest film of all time, we'll give Lohan her due, even though she was far more believable as bitchy Plastic Cady than as the fresh-out-of-Africa Cady, for some reason.
4. Casey Stuart in Life-Size
In case you weren't plugged into the Disney Channel in the early aughts and need a refresher, Life-Size is a movie in which a Barbie doll magically transforms into Tyra Banks. She ends up living with a very young LiLo, whose character recently lost her mother and plays quarterback on her middle school football team. Barbie Tyra teaches LiLo how to love herself and come to terms with her mother's death, all the while developing a sort of creepy romantic relationship with LiLo's father. SPOILER ALERT: Barbie Tyra eventually transforms back into a doll, but it's okay. LiLo takes her lessons to heart. Hillary Swank won an Oscar for Boys Don't Cry that year, but someone else was ROBBED.
5. Aubrey Fleming / Dakota Moss in I Know Who Killed Me
Perhaps the 7 percent "rotten" rating on Rotten Tomatoes has turned you off of this cinematic wonder, but you are MISTAKEN, dear reader. This film has everything: a murder plot, a super awkward sex scene (NSFW), LiLo stripping (also NSFW), lots of dismemberment, and (SPOILER ALERT!) even more evidence of LiLo's predilection for double roles. To be fair, I watched this movie back when I was drinking a lot of Everclear, and I'm not entirely sure what it's about, or whether I was even able to tie my shoes during this period. But it seemed awesome! I think.
BONUS: Whatever role LiLo plays in The Canyons
Just because we haven't seen LiLo's tour de force with porn king co-star James Deen, doesn't mean we don't want to.
Tagged
lilo
Lindsay Lohan
mean girls
original
Rebecca Fishbein
Read more
Gothamist is funded by sponsors and member donations
Gothamist is funded by sponsors and member donations
MORE arts-entertainment
The hottest way to show you're an authentic New Yorker is… riding a Citi Bike?
Thanks to Dua Lipa, Kim Kardashian, Timothée Chalamet and more, the rideshare program is having a moment.
By
Lindsay Lee Wallace
Published Oct 8, 2026
Is NYC’s hottest attraction the free observation deck at 1 Centre Street?
If you're playing tourist in your own town, this is an in-demand option.
By
James Ramsay
Arts & Entertainment
Is NYC’s hottest attraction the free observation deck at 1 Centre Street?
If you're playing tourist in your own town, this is an in-demand option.
By
James Ramsay
What happens when NYC kids take lessons in rock music? Really good bands.
By
Jayson Greene
Inside a photographer's journey to visit every neighborhood in New York City
By
Sonia Rao
Banned books and Winnie the Pooh: October in NYC libraries
By
Alec Hamilton
Never miss a story
Catch up on the most important headlines with a roundup of essential NYC stories, delivered to your inbox daily.
Sign upEmail address
By submitting your information, you're agreeing to receive communications from New York Public Radio in accordance with our Terms .