5. Herbie Fully Loaded (2005)
Herbie isn’t a Lindsay Lohan movie, it’s a car movie that she’s the main human in. It’s still important to her filmography, though!
Herbie is the kind of film you show at a drive-in to get the Millennials to come and watch a movie in the era of streaming, and there’s no question that the film is entertaining, heart-warming, and just plain fun.
In contrast to many of her roles, Lohan plays more of a tomboy here and she doesn’t miss a beat. Her exasperation as Herbie drives himself down the freeway seems genuine, and she plays the moments of physical comedy well. There’s a real feeling of a relationship between a person and a sentient vehicle learning to work in concert. What more could one ask for from such an absurd race film that doesn’t involve Vin Diesel?
4. Confessions of a Teenage Drama Queen (2004)
Based on the eponymous novel, Confessions of a Teenage Drama Queen is one of many films that aim to show the quirky side of the 2000s’ American high school experience. It stars Megan Fox as the film’s resident mean girl, and there’s a confluence of female talent behind the camera (though not operating the camera, strangely enough).
Lindsay Lohan stars as Lola, an individualistic teen from the big city who tries to thrive in suburbia through dreams and fantasies. This film shows how effectively Lohan can convey character when it’s defined beyond the blandness of the average teen film or rom-com.
Lola comes across as someone who is fighting to remain herself in a world filled with disillusionment. Her fashion in this film really stands out, and feels somewhat more genuine to her character than it generally does in the Disney film machine.
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3. Mean Girls (2004)
There are many films that explore the hierarchical dynamics of American high school, but none pull it off in the same way as Mean Girls.
Lindsay Lohan wanted to play head Plastic Regina George (Rachel McAdams), but she was cast in the lead role of Cady instead. Cady is another high school outsider, a role Lohan was all too familiar with. But, instead of existing on the periphery, Cady comes into her own, becoming her own form of diva and losing herself along the way.
Mean Girls is one of the best-remembered films of its era, and Lohan’s performance contributes to making it great. She is believable as a mean girl aiming to bring down Regina with her catty remarks and false persona. But Lohan seems effortless as the real Cady, a kind math nerd who is naïve about the harsh realities of the American school system.
Lohan brings plenty of star talent to the excellent ensemble cast, and it isn’t up for debate that this role is in her top three.