Lindsay Lohan was one of the biggest young stars of the 2000s, but which of Lohan's movies is the best? Starting as a prominent child actor before growing into a bona fide box office sensation, Lohan starred in a string of big hits throughout the late 1990s and well into the first decade of the 2000s. Most known for playing girl-next-door teens and hopeless romantics, Lohan showed off a surprising range of talent even when starring in movies that fell far below critical expectations. Though she's been a celebrity since childhood, Lohan's greatest strength has always been her affable and down-to-earth screen presence.
As is usually the case with child stars, Lohan's career has not been a straight ascent, and the former A-lister went through a rough patch as she entered adulthood that saw much of her working output decline. However, she has seen a resurgence of late, and Lohan's two-movie deal with Netflix showed that interest has perked up in the versatile actor. While she has yet to return to the heights she once enjoyed, the overwhelming response to Lohan's "comeback" in 2022 shows that she is still an in-demand performer who never really lost the luster that she once had.
10 Life-Size (2000)
Between her years as a child actor and her impressive stretch as a teen superstar, Lohan cemented herself as the definitive 2000s tween star. Life-Size is a made-for-TV movie starring Lohan as Casey Stuart, a young girl who accidentally brings her doll to life while trying to resurrect her recently deceased mother. Despite its somewhat jarring premise, Lohan delivered a compelling performance that spoke to the deeper meaning behind the film's odd story. Though she was somewhat overshadowed by Tyra Banks' turn as the doll, Lohan showed glimpses of what would make her such an in-demand actor who could carry any movie.
9 Machete (2010)
Robert Rodriguez's tongue-in-cheek B-movie tribute film Machete featured a strong ensemble cast, including Lohan in an uncharacteristic role. The film centers on a dangerous ex-Federale who is double-crossed by the powerful criminals who hired him as an assassin. Stuffed with over-the-top action and gore, Machete was a love letter to 1970s grindhouse cinema, and Lohan's turn as wild-child socialite April was appropriately outrageous. Though the film glorifies certain problematic elements of Machete's character, especially regarding his treatment of April, Lohan shined in a role that was clearly meant to express that she wasn't a child star anymore.
8 Get A Clue (2002)
While most Lohan movies were released theatrically, she starred as a precocious teen detective in the made-for-TV Disney Channel movie, Get a Clue. In the film, high school gossip columnist Lexy Gold (Lohan), must team with her rival to solve the case of a missing teacher. Though it was one of Disney Channel's more unrealistic original movies, it was nevertheless a cleverly plotted and intricate mystery. Lohan settled in nicely into the "mean girl" type character, and Get a Clue could have easily been released theatrically with only a few budgetary upgrades.
7 Just My Luck (2006)
Though she was at the height of her fame in 2006, Just My Luck is often overlooked among Lohan's movies. In the film, Lohan plays Ashley Albright, a young socialite with unbelievable luck who accidentally loses her gift after kissing a stranger at a costume party. Though poorly reviewed, the film had all the makings of a rom-com hit and even featured Chris Pine in an early-career role. Lohan's character has an engaging arc befitting of great rom-coms, and she turned in a strong performance that far outshone the somewhat lackluster script. Additionally, Lohan even managed to make the convoluted premise believable.
6 Herbie Fully Loaded (2005)
Having previously provided a hit remake for Disney in the form of 1998's The Parent Trap, Lohan was tapped to star in another reboot attempt from the studio. Herbie Fully Loaded follows Lohan as Maggie Peyton, a young woman who dreams of racing in NASCAR and is gifted a magical car named Herbie. Fast-paced and fun, Herbie Fully Loaded captured the original spirit of the Herbie series but with a distinct 2000s flare. Despite lackluster reviews, the film was a financial success (via Box Office Mojo) and that was due in large part to Lohan's star power and box office appeal.
5 Falling For Christmas (2022)
2022's Falling for Christmas is heralded as Lohan's official comeback movie, and the Netflix original did a lot to remind viewers of their love for the '00s star. The story centers on young heiress Sierra Belmont (Lohan) who suffers amnesia after a skiing accident and spends a quaint Christmas at a small lodge where she comes to love the simpler things. Falling for Christmas had all the cheesy goodness expected from holiday movies, and Lohan was back in her element, playing the role of Sierra in two totally distinct ways which was essentially two characters in one.
4 Confessions Of A Teenage Drama Queen (2004)
Though it was made released the same year as a more successful Lohan movie, Mean Girls, Confessions of a Teenage Drama Queen is a nostalgic time capsule to the mid-'00s. Lola (Lohan) is an aspiring stage actress whose dreams are put on hold when her family moves from New York City to suburban New Jersey. In addition to Lohan, Confessions of a Teenage Drama Queen featured a cast of young talent including Megan Fox and Allison Pill. While it was massively overshadowed by Mean Girls, Confessions of a Teenage Drama Queen is still the quintessential Lohan movie experience.
3 The Parent Trap (1998)
The film that put Lohan on the map, The Parent Trap allowed the burgeoning young star to pull double duty in her feature debut. Identical twins, Annie and Hallie (Lohan), meet for the first time after being separated at birth and concoct a scheme to reunite their parents. 1998's The Parent Trap still holds up today in ways its 1960s original did not because it not only updated the story but was anchored by a stellar performance from a young Lohan in two roles. The soon-to-be child star delighted by giving both twins their own distinct personalities, and she employed dramatic talents that would eventually serve her in other films.
2 Freaky Friday (2003)
Walt Disney Pictures couldn't miss with Lohan as the star of their movies, and Freaky Friday was yet another successful collaboration. In the film, a feuding mother and daughter pair (Jamie Lee Curtis and Lohan) magically switch bodies and have to live each other's lives until they can find a way to switch back. The fun body swap premise was elevated by the electric onscreen chemistry between Curtis and Lohan. As with previous roles, Lohan essentially played two different characters and the result was hilarious. In the end, Freaky Friday's real power was its strong message of acceptance and understanding which added heart to the movie's abundant levity.
1 Mean Girls (2004)
Undoubtedly a shining example of mid-'00s popular cinema, Mean Girls had a profound impact on Lohan's movie career and pop culture in general. Penned by comedy giant Tina Fey, the film follows Cady Heron (Lohan), a sheltered teen who tries to find her place in the delicate ecosystem of high school cliques. Following in the footsteps of iconic teen movies like Clueless, Mean Girls summarized the aughts experience succinctly and achieved icon status. Lindsay Lohan essentially played the "straight man" against more verbose performances by Rachel McAdams and Amanda Seyfried, and developed one of her most beloved characters in the process.
