In the 2000s, millennials crowned auburn-haired Lindsay Lohan as the teen idol of the era. Unfortunately, like many child stars, Lohan had a difficult time in the industry and took a decade-long break in the 2010s. Still, her films from the late 1990s and mid-2000s remain generational touchstones and comedy classics.
Lohan's more grown-up work is less popular, though there are a few gems in her filmography that she deserves more credit for. More recently, Lohan launched something of a comeback with
her series of popular Netflix films, putting her name back on the proverbial marquee once more.
Films aimed at kids and teens aren't always given serious consideration, and Lohan hasn't had the easiest time pleasing critics and keeping the press on her side. In fact, it's high time we evaluate Lohan's work with clear eyes and enough hindsight to recognize her talent and charisma for what it is.
Whether you're a die-hard fan or a skeptic, join us for a journey through Lindsay Lohan's best movies.
Read more: The 15 Best 'So-Bad-It's-Good' Movies Of All Time
Falling For Christmas
Netflix Christmas movies operate with their own unique set of rules, making them difficult to consider using standard movie metrics. Indeed, these films are not meant to be "good" so much as they are meant to push the limits of what constitutes watchable nonsense. Lohan has made two of these films so far, as well as one equally ludicrous but non-holiday-themed rom-com. "Falling for Christmas," the best of the trio, is great for a laugh as long as you don't think about it too hard.
Lohan plays Sierra Belmont, the vapid hotel heiress of an expensive ski resort in Aspen. While skiing with her insufferable boyfriend, Tad (George Young), Sierra falls and hits her head. When she wakes up, she has no idea who she is. The friendly proprietor of a quaint bed and breakfast, Jake (Chord Overstreet), comes to her aid and gives her a place to stay.
Will Sierra choose the simple life with the man she loves or the life of luxury she's accustomed to? While we ponder this all-important question, Sierra learns how to be a normal human being without a maid or assistant to do everything for her. For Lohan, this is a return to form. Coming back to her roots as an adorable goofball, Lohan gives her all to these fantastical shenanigans, contributing a worthy (read: unhinged) entry to the Netflix Holiday Movie Cinematic Universe.
Get A Clue
In the 2002 film "Get a Clue," Lindsay Lohan uses her penchant for believably getting involved in unbelievable hijinks to great effect. Having graduated from precocious child to precocious teen, Lohan plays Lexy Gold, a 13-year-old who works as an advice columnist for her school newspaper. A wealthy Manhattanite with a highly developed sense of style, Lexy becomes embroiled in a mystery when her teacher, Mr. Walker (Ian Gomez), goes missing. Lexy attempts to solve the mystery alongside her friend Jen (Brenda Song), classmate Gabe (Ali Mukaddam), and her nemesis, the paper's editor, Jack (Bug Hall).
The caper that follows is just absurd enough to be enjoyable. Lexy and her classmates encounter a heist, a $10 million diamond, and even a hostage situation. Luckily, they have plenty of high-tech gadgets à la the Kristen Stewart movie "Catch That Kid," so they're able to save the day.
An underrated entry in the Disney Channel Original Movie canon, "Get a Clue" delivers on its promise. It's absolutely silly, but that's the point. The always-lovely Brenda Song is sweet as Lexy's BFF, and Lohan marshals all of her considerable confidence to portray such a larger-than-life character. And get a load of those clothes! The film's era-specific fashion has to be seen to be believed, as do Lexy's sharp journalistic instincts. It's not a masterpiece, but it is a goofy good time.
Bobby
One of the least-remembered films on Lohan's resumé, "Bobby" isn't a bad film by any means. The film takes place in the hours before the assassination of Robert F. Kennedy in 1968. Directed by Emilio Estevez, the ensemble cast features big names like Harry Belafonte, Laurence Fishburne, Helen Hunt, Anthony Hopkins, Demi Moore, and Martin Sheen. We follow the lives of 22 different people as their paths intersect and reflect the complex issues of the era.
Lohan plays Diane Howser, a young woman planning to marry her friend William (Elijah Wood) to prevent him from being drafted. A distinct departure from her previous projects, Lohan's presence in the film seems intended to prove her worth as an actress. At the time of the movie's release, Lohan was in the news for her disorderly behavior and love for partying, and had received bad press for her tardiness during the filming of "Georgia Rule." However, Estevez defended Lohan, telling Oprah that she was a professional during the shoot and gave "the best work of her life."
Lohan's performance in the film is impressive, as evidenced by a scene where she acts opposite Sharon Stone, explaining her decision to marry William in order to "save a life." Unfortunately for Estevez, he's no Robert Altman, whose film "Nashville" was a clear inspiration for "Bobby." The ensemble is larger than necessary, and some storylines fall flat. But for Lohan, the film marked a unique turning point in her career.
Just My Luck
Her first foray into the world of adult rom-coms, "Just My Luck" sees Lindsay Lohan starring alongside veritable heartthrob Chris Pine. The plot of the film makes little sense, but here's a synopsis, just for kicks. Lohan plays Ashley, a PR executive with incredible luck. Pine plays Jake, a janitor with dreams of becoming a music producer. (He manages the real-life British band McFly.)
At a masquerade ball for her firm, Ashley dances with Jake, and they share a kiss. With this liplock, Ashley transfers her luck to Jake. Things start taking off for Jake career-wise, while Ashley loses her job and apartment. A fortune teller informs Ashley that someone else has else has her luck, so she sets out to find the mysterious man she kissed at the ball. We learn that Ashley's luck can transfer from person to person only through kissing, kind of like the demon from "It Follows," but much more whimsical. (If you're wondering who came up with this hair-brained plot, it's co-writer I. Marlene King, also known as the showrunner of "Pretty Little Liars.")
Is Lindsay Lohan's character actually a superhero in this film? Is falling in love with Chris Pine the worst thing that could happen to a person? Do human beings have free will? "Just My Luck" doesn't answer any of these questions, nor is it the highlight of Lohan's career, but as a diverting popcorn flick, you could do much worse.
Life-Size
Supermodel and business mogul Tyra Banks has acted in more TV and film projects than you'd think, from "Coyote Ugly" and "Love and Basketball" to episodes of "Felicity" and "Gossip Girl." But by far her greatest contribution to cinema is her role in the 2000 film "Life Size," where she plays a doll come to life. Lindsay Lohan plays Casey, a 7th grader struggling with the death of her mother. Casey tries to cast a spell to resurrect her mother, but the spell goes wrong and she accidentally brings a doll to life instead.
When Eve (Banks) wakes up as a human being, she's thrilled. Unfortunately, she's not very good at acting like a human, as evidenced by her attempt to be a secretary (typing nonsense into a computer) and her dangerous inability to cook. While Eve's presence frustrates Casey at first, she eventually helps Casey come to terms with the loss of her mother. Meanwhile, Eve discovers sexism and finds she doesn't like it very much.
Sometimes called the original "Barbie" movie, "Life-Size" deserves some credit for originating the human-sized doll story. More than that, the movie is legitimately hilarious, and it makes use of Banks' inherent strangeness to great effect. How can you hate a movie that features a life-sized doll singing her theme song -- an empowerment anthem called "Be a Star" -- at a corporate event? You can't.
Confessions Of A Teenage Drama Queen
Let's be clear: The critics that gave "Confessions of a Teenage Drama Queen" its low rating on Rotten Tomatoes were wrong. It's not that these critics were bad at their jobs, per se, but rather they had forgotten (or never known) what it's like to be a teenage girl. Our beloved Lindsay Lohan plays Lola, a 15-year-old New Yorker with Broadway dreams. Though devastated when her family moves to suburban New Jersey, Lola decides to try and conquer her high school like the queen she believes herself to be, much to the chagrin of popular girl Carla (Megan Fox, also in one of her best movies).
Clearly made for teens and adolescents, "Confessions of a Teenage Drama Queen" succeeds heartily as a full-throttle farce without profound aspirations. Lohan delivers a hilarious voice-over that introduces viewers to Lola's melodramatic tendencies and gives us insight into why she becomes a pathological liar to achieve popularity and success.
As usual, Lohan puts her charm to good use, faithfully conveying Lola's teenage insanity while also bringing her back down to earth. Fox is well-cast as a high school mean girl, an archetype she played into brilliantly in the cult classic "Jennifer's Body." You either buy into the plot of the movie, or you don't, and if you have enough childlike wonder left to enjoy it, you'll find that "Confessions of a Teenage Drama Queen" is one of the most preposterously funny films in Lohan's oeuvre.
Machete
Defying the usual order of things, Robert Rodriguez made a trailer for his film "Machete" before the project even began. The film first appeared amongst a group of fake trailers in "Grindhouse," a gory double feature from Rodriguez and Quentin Tarantino. "Machete" stars Danny Trejo as the title character, a former Mexican Federale with a score to settle. (Technically, "Machete" marks the third time Trejo played this character, which first appeared in "Spy Kids" as part of the Robert Rodriguez cinematic universe.)
When a racist Texas Senator (Robert De Niro) hires Machete to perform a hit and double crosses him, Machete goes on a bloody rampage to get revenge on his former employer. Other characters include a taco-slinging revolutionary (Michelle Rodriguez), a conflicted immigration officer (Jessica Alba), a Mexican drug lord (Steven Seagal), and a gun-toting priest (Cheech Marin). Disney's own Lindsay Lohan plays April, a drugged-up socialite who joins the party wielding a gun in a nun's habit.
Less a narrative film and more a series of set pieces, jokes, and action sequences, "Machete" nonetheless delivers on its B-movie premise. Less successful at landing its message about anti-Mexican racism and xenophobia, the film's self-awareness and commitment to having a good time make it just that. Though she got the part at a low point in her career, Rodriguez was impressed with Lohan's work in the film and even floated the idea of a LiLo-centric spinoff.
Herbie: Fully Loaded
When you think about it, most of the films in Lindsay Lohan's filmography hinge on a fantastical premise that requires audiences to believe in magic, or at least throw out the rules of logic for a little while. "Herbie: Fully Loaded" is one such film, and it comes from a long line of whimsical stories. The sixth film in a long-running series, "Herbie: Fully Loaded" centers on a sentient Volkswagen Beetle named Herbie. Lohan plays Maggie Peyton, an aspiring NASCAR driver. Maggie's father (Michael Keaton) doesn't want her driving because it's too dangerous, but when she meets Herbie, her fortune changes.
Critics didn't love the film upon its release in 2005, but "Herbie: Fully Loaded" doesn't get enough credit and remains one of Disney's most underrated films. Director Angela Robinson leans into the film's inherent strangeness while also slowly getting us to believe that its magical realism isn't so far-fetched. Though Herbie doesn't have a human voice and is quite literally just a car, he somehow has a personality distinct enough to propel the film. And you've got to give major kudos to Lohan, who manages to act opposite a piece of machinery as if it were her flesh and blood companion. A comedy, a sports movie, and a fantasy film, "Herbie: Fully Loaded" represents a cheerful moment in Lohan's teen star era.
A Prairie Home Companion
As strange as it sounds, we're grateful for whichever stars had to align for Lindsay Lohan to star in the last movie from legendary filmmaker Robert Altman. His 2006 film "A Prairie Home Companion" takes place during the final show of the beloved Minnesota radio show of the same name. Lindsay Lohan plays Lola, one of the singing Johnson Girls, which includes her mother, Yolanda (Meryl Streep), and aunt Rhonda (Lily Tomlin). The cast also features Woody Harrelson, John C. Reilly, Maya Rudolph, as well as Garrison Keillor, host of the real radio show.
"A Prairie Home Companion" deals directly with the encroachment of death (one of the characters is a literal angel), a timely topic for Altman at the end of his life. But despite this serious topic, the film has an earnest sweetness to it, depicting the "death" of the show as an inevitable step forward for the folks behind the broadcast.
As in most of Altman's films, "A Prairie Home Companion" strives for naturalism, favoring long takes and overlapping conversations over distinct scenes or lengthy monologues. Lohan was just 19 years old when the film premiered, and it represented a major departure from her previous kid and teen-centric work. The cherubic sweetness of her earlier performances translates well in this context, and the film represents a high point in Lohan's career just as the tabloids began a decade-long attack on her off-set behavior.
Freaky Friday
Would you believe us if we told you Quentin Tarantino has a favorite scene in the "Freaky Friday" remake from 2000? Well, it's true, and it proves that the controversial director does have good taste, after all. The movie follows single mother Tess (Jamie Lee Curtis) and her teenage daughter Anna (Lohan) as they navigate their conflict-ridden relationship. When they switch bodies because of a magical fortune cookie (don't ask), they're quite literally forced to walk in each other's shoes as they try and figure out how to undo the spell.
"Freaky Friday" features great performances from both Curtis and Lohan, who fully commit to the physical comedy required of them. They have delightful chemistry, both when Curtis plays the mother and Lohan the daughter and when their roles are reversed. The weirder parts of their body-swap situation (namely, the involvement of their love interests, played by Chad Michael Murray and Mark Harmon) are dealt with brilliantly, keeping any gross-out moments to a minimum.
Though it's an unabashedly silly movie, "Freaky Friday" still retains an element of cool, in large part due to Anna's alt-rock band, Pink Slip. It's always fun when Lohan gets to flex her singing chops alongside her acting skills, and "Freaky Friday" succeeds in large part because of how well it utilizes her best qualities as a performer.
The Parent Trap (1998)
When you watch Lindsay Lohan's earliest work, it becomes abundantly clear that her (often underrated) acting talents manifested themselves at a young age. Nowhere is this more obvious than in "The Parent Trap," her first film and her first smash hit. Directed and co-written by rom-com icon Nancy Meyers, the movie follows twins Annie and Hallie (both played by Lohan), who were separated at birth. When they meet by chance at summer camp, they hatch a plan to swap identities and get to know their estranged parents.
Dennis Quaid plays the twins' American father, while the late Natasha Richardson plays their British mother. (Lohan also sports an impressive British accent as Annie.) Elaine Hendrix plays a 26-year-old gold digger planning to marry the twins' father, while Lisa Ann Walter plays Cheesy, Hallie's nanny. Both characters have had a long shelf life and remain common pop culture references.
While the film's entire cast is impressive, Lohan's performance is what makes "The Parent Trap" one of the best kids' movies of all time. Though she plays the sometimes grating cinema archetype of the precocious, scheming child (or children, in this case), Annie and Hallie both feel like fleshed-out characters with their own inner worlds and motivations. Some of this is due to Meyers' script, but it's Lohan who gives Annie and Hallie that playful spark and the infectious confidence found in many of her adolescent roles.
Mean Girls
Quite a few of Lindsay Lohan's films remain beloved by viewers who watched them when they were younger, but none of her projects come close to reaching the cultural impact of "Mean Girls." Arguably the most-quoted movie of the 21st century, "Mean Girls" is more than just a series of meme-able moments -- it's also one of the greatest comedies of its era. Lindsay Lohan plays Cady Heron, a teenager who grew up in Africa and finds it difficult to manage high school life in America.
Written by Tina Fey, the film offers biting commentary about cliques and the arbitrary ways people, especially women, are categorized. But more importantly, "Mean Girls" contains a wealth of jokes and hilarious moments that have stood the test of time, even if the film takes place in a bygone era. With an incredible cast that includes Fey and BFF Amy Poehler alongside rising stars like Rachel McAdams and Amanda Seyfried, the movie's formula has proved difficult to imitate, though many have tried.
While cutting and occasionally cruel, Lohan's relatable, girl-next-door charm gives the film the warmth and heart it might otherwise lack. It's been over 20 years since "Mean Girls" made fetch happen at the box office, and nothing Lohan has done since has come anywhere near reaching its success. But while Lohan's time as a teen idol has come to an end, many of her films continue to delight viewers all these years later.
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