The early 2000s were a time of Limewire, low-rise jeans and Lindsay Lohan’s cinematic universe. Back then, she was the face of young adult movies, having led numerous films before even the age of 20. Her success earned her total teen stardom, winning multiple accolades, including Best Performance in a Feature Film from the Young Artist Awards. Essentially, at the time, it was impossible not to know her name. To this day, she has acted in over 20 movies, from family films to romance and drama.
Though Lohan moved on to more mature characters like the psychological thriller, I Know Who Killed Me and the Elizabeth Taylor biopic, Liz & Dick, everyone knows she was at her prime in teen comedies. She, after all, managed to make audiences believe she had a British twin, executed the role of a 40-year-old mother of two at 17, and gracefully fell into a trash can whilst strutting through North Shore High School. Not to mention, she was acclaimed enough to star as herself in the animated Barbie film My Scene Goes Hollywood. The 34-year-old is making her way back to the rom com scene, starring in Netflix’s upcoming Christmas film, Falling for Christmas, but until then, here are some of Lohan’s best teen movies, ranked.
7 Get a Clue
Once upon a time, industries could pump out a hit on only a $1 million budget, and that’s the case for 2002’s Get a Clue. Lohan starred with Ian Gomez, Bug Hall and Disney Channel superstar Brenda Song. Perhaps Lohan’s darkest role as a teenager, the mystery filmed revolved around the disappearance of the school’s teacher Mr. Walker, after Lohan’s character Lexy, publishes an article about him in the school newspaper.
6 Herbie: Fully Loaded
The sixth and final installment of The Love Bug franchise, Lohan starred as Maggie Peyton, the newest owner of Herbie the Volkswagen Beetle in Herbie: Fully Loaded. Through racing, derbies, and strict fathers, Maggie goes on to become a professional NASCAR driver. The movie was more of a spinoff, rather than a continuation, as it did not connect to the previous films. It was met with mixed reviews from critics, having received a 41% on Rotten Tomatoes. Still, it was able to make over $140 million at the box office, against a $50 million budget.
5 Confessions of a Teenage Drama Queen
In 2004's Confessions of a Teenage Drama Queen, Lohan took the role of Mary Elizabeth Steppe, aka “Lola,” the actress, compulsive liar and titular “drama queen.” Living her life like she is in a movie, Lola has the biggest dreams of becoming a Broadway star. While the theatrical film was still a Disney production, it was the first of Lohan’s to not be a remake of some sort. Lohan got her shining moment performing the pop song, “Drama Queen” which won the Radio Disney Award of “Best Song to Watch Your Dad Sing.”
4 Life-Size
In 2000, The Wonderful World of Disney debuted this fantasy-comedy, starring Lohan and supermodel Tyra Banks. Lohan took on the role of Casey Stuart, the 13-year-old embodiment of “not like other girls.” After the football-playing tomboy was granted an “Eve” Doll for her birthday, she wakes up to a living, life-sized Black Barbie in her bedroom. Though Casey wasn’t a fan of Eve in the beginning, she goes on to treat her as another member of her family, just before the heart-wrenching ending where Eve returns to Sunnyvale, where she belongs in doll form. The film went on to have a holiday sequel titled A Christmas Eve and though Lohan did not return, her character Casey was mentioned and seen in a photo. Oddly, the sequel is available on Disney+, but the first film is hard to locate on any streaming service.
3 Freaky Friday
Lohan’s highest grossing film to date is Freaky Friday, which earned $160 million in the box office. This 2003 hit was just one of Disney’s four interpretations of the ole’ mother-daughter switcheroo. Previously, the film had been produced in 1976 and 1995, with a musical remake in 2018. In this version, Lohan starred as Anna, the rebellious teen rocker whose body is switched with her uptight mother, Tess (Jamie Lee Curtis). Not only did Lohan once again capture teenage melodrama, she also perfectly embodied the role of a strict psychologist. Seriously, who can forget the way Lohan, as Tess, awkwardly frolicked across stage, pretending to play guitar as Curtis’ character completely shredded her rock solo backstage.
2 The Parent Trap
Lohan made her film debut in Disney’s 1998 remake of The Parent Trap, alongside Dennis Quaid and Natasha Richardson. She starred as both Annie and Hallie, two formerly estranged twins who reunite at summer camp and conjure a plan to get their divorced parents back together. When casting for the role, director Nancy Meyers said she was in search of a “little Diane Keaton,” and at only 11 years old, Lohan already displayed a great deal of range through tears, wit, heartfelt-ness, and obviously, the use of two different accents. The roles earned Lohan the aforementioned Young Artist Award, as well as an award for Best Breakthrough Performance from Online Film & Television Association.
1 Mean Girls
Mean Girls may have been brought to the silver screen as just another chick flick, but to this day, the film is seen as a cult classic. The jokes, the quotes, the realness of high school drama, Mean Girls goes down in history as one of the best teen films ever. The MTV Award-winning motion picture was Lohan’s first non-Disney feature and according to Brandon Gray of Box Office Mojo, “cemented her status as the new teen movie queen.” The movie was successful enough to have gotten an infamous sequel, a Broadway musical and an upcoming musical remake. At the moment, not much is known about the new movie, but one can hope Lohan will at least make a cameo.