11 of Lindsay Lohan’s Best Movies for Your Y2K Watch Party

Admit Lindsay Lohan is the actress of our generation, or get out. Quickly. With range for miles, Lindsay spent her childhood playing every single type of character—we're talkin' tomboy, Material Girl, dramatic theatre kid, charming British overnight camper, and Homeschooled Jungle Freak™️, to name quite literally a few.

By the time she was 12, Lindsay was a bonafide household name for the cinematic chokehold she had us all in. Throughout the late 2000s though, we were seeing and hearing her name for different reasons—mainly in tabloids rather than movie screens.

So you may be wondering what has our girl been up to since all of *that*? Well, in 2019, MTV debuted Lindsay Lohan’s Beach Club, a reality series focused on her VIP vacation club Mykonos Beach House. But it didn't stop there: During an appearance on CNN’s New Year’s Eve special in 2019, Lindsay stated that she was resuming her acting career! Rejoice! And it gets better: In March 2021, Lindsay signed a multi-film deal with Netflix, promising several new films including a holiday flick, Falling for Christmas, set to be released this year.

So, TL;DR—LiLo is back, baby! Whilst we wait for her new projects, consider this list of her 11 best movies required viewing.

The Parent Trap

A Nancy Meyers script + the late Natasha Richardson + Dennis Quaid + Lindsay Lohan and...more Lindsay Lohan = the perfect recipe. The iconic 1998 film follows a pair of identical twins who were separated at birth and grew up thousands of miles apart. The duo, Hallie and Annie (both played by Lindsay), reunite at a sleep-away summer camp and ultimately decide to switch places to spend time with the parent they don't live with. Once they get busted, the twins devise a plan to bring their parents back together, despite the struggles of distance and an iconic evil stepmother, the original baddie Meredith Blake.

Life-Size

If you didn’t already know that a movie starring Tyra Banks and Lindsay Lohan exists, welcome to peak cinema. Life-Size premiered in 2000 and follows a tomboyish girl whose Eve doll (like Barbie without the branding) comes to life. Lil warning: The premise is actually kind of sad. Lindsay’s character Casey finds a magical book at a local bookstore that features a resurrection spell. Casey completes the spell, hoping to bring back her deceased mom, but instead, she brings her doll to life in a classic supernatural hair strand mix up. Casey is, naturally, devastated. Eve is, naturally, thrilled and feeling the lust for life. Cue tween girl and life-size Barbie doll adventures. There is also an *iconic* singing and dancing scene, so prepare for it to be locked in your head for weeks after watching.

Get A Clue

This 2002 Disney Channel Original Movie stars LiLo as Lexy Gold, a Prada-clad teen super sleuth à la Nancy Drew, investigating the disappearance of her teacher in New York City. Fun fact for whenever you hit the next Lindsay Lohan trivia night: At just 16 years old, Lindsay had already landed a three-movie deal with The Walt Disney Company, which gave the world the aforementioned Life-Size, Get A Clue, and Freaky Friday. Speaking of which...

Freaky Friday

Another LiLo classic, this story follows a bickering mother and daughter who swap bodies in a Chinese restaurant, forcing them to live the other’s life for days. Lindsay stars as a rebellious emo girl, with Jamie Lee Curtis playing her classy, slightly uptight therapist mother. Upon its release Freaky Friday became an instant sensation and also brought the world one of Lindsay’s best songs, “Ultimate.”

Mean Girls

If you’ve somehow made your way to this article without having seen Mean Girls at least once (or 30 times) in your life, YOU CAN'T SIT WITH US. The 2004 comedy was written by Tina Fey and stars Lindsay as Cady Heron, a homeschooled jungle freak teenage girl who enrolls in an affluent suburban public high school after a lifetime of homeschooling in Africa. Cady's new school introduces her to a host of characters not unlike the wild African food chain she had come to know. Instead of continuing to summarize the plot of a movie that is essentially required reading for anyone ever, we’ll take this time to honor a few classic Mean Girls quotes:

 

"It's like I have ESPN or something. My breasts can always tell when it's going to rain."

"One time, she punched me in the face. It was awesome."

"Your mom's chest hair!"

 

Confessions of a Teenage Drama Queen

LiLo’s teen royalty continued through 2004 with Confessions of a Teenage Drama Queen, which is nothing short of ~high art~. Lohan plays Lola Steppe, a sequin-laden 15-year-old brat with massive Broadway dreams and the dramatics to match 'em. To her dismay, her parents move her from the Big Apple to New Jersey, where she falls into a bad habit of lying to bedazzle her backstory.

Just My Luck

This 2006 rom-com is simpler than most. A girl with good luck kisses a boy with bad luck, and they end up swapping spit...and fortunes. Lindsay plays the luckiest It Girl in Manhattan, Ashley Albright, opposite Chris Pine’s unlucky Jake. It’s your classic 2000s rom-com: a New York backdrop, a leading lady with an alliterative name and a sexy job in public relations, a masquerade charity ball, and an inevitable (and unlikely) love story.

Herbie: Fully Loaded

Looking for a LiLo movie you can watch with your dad? Presenting Herbie: Fully Loaded, which features cameos from real NASCAR legends so you can point to the screen and say “See!” while he grunts. The 2005 film is a sequel to the 1997 film, The Love Bug, and stars Lindsay as the youngest daughter of a racing family who chooses Herbie the Volkswagen Beetle from a junkyard as a graduation gift. In case you haven’t seen the original film, Herbie is sentient. Do with this information what you will.

Georgia Rule

Garry Marshall’s 2007 comedy, Georgia Rule, stars LiLo alongside icons Jane Fonda, Felicity Huffman, and Dermot Mulroney. Lindsay plays a rebellious teenager with alcohol and drug dependencies, sent to live with her grandmother in Idaho. Her character Rachel is forced to swap drinks and drugs for God and hard work, all the while harboring a dark secret about her family.

Liz And Dick

In this 2012 television film, Lohan plays Elizabeth Taylor opposite Grant Bowler’s Richard Burton. The film follows the torrid relationship between the two stars who made eleven films together in an excess of alcohol and scandal.

The Canyons

Lindsay and James Deen (no, not that James Dean) star in Paul Schrader’s 2013 thriller that follows Christian, a trust fund movie producer in Los Angeles who learns that his girlfriend Tara (Lindsay) is having a secret affair with the star of his project. Oop!