Lindsay Lohan’s Top 10 Movies Ranked: From Best to Worst

Lindsay Lohan appears to be having a very good summer. Freakier Friday, the Freaky Friday sequel that reteams her with Jamie Lee Curtis, is her highest-profile movie in some time, and it returns her to the Disney entertainment empire that made her a star, at age 12, with 1998’s The Parent Trap.  

Anyone who’s followed Lohan over the years (and it would have been hard not to) knows that a survey of her career will encounter lapses, stumbles, gaps and dry spells, especially after 2012. By then, vaulting from one sensational headline to the next without a safety net, she’d been to rehab at least five times, done 67 days of community service and spent more than a week in jail. 

None of these troubles, though, robbed her of her star magnetism, which still seems to situate her in a mysteriously fluid zone — sometimes touching, sometimes awkward, always attractive — between adolescence and adulthood.

Now 39, a wife and doting mother to son Luai, Lohan said she wants to avoid overcrowding her life with projects, but seems eager to keep exploring new work. Freakier Friday costar Curtis has even suggested an ideal project for her longterm friend: a biopic of another famous redhead, actress Ann-Margret. (And if you watched the actress in the opening sequence of 1963’s Bye Bye Birdie , you can imagine Lohan — always a talented musical performer — charging toward the camera in her place).

Below, here’s my ranking of Lohan’s top 10 movies, ordered from best to worst.

1. The Parent Trap (1998). Lohan’s preteen performance in this silly, frothy comedy comes very close to matching Macaulay Culkin’s in Home Alone. Playing identical twins who meet for the first time at summer camp, Lohan manages to give one of the sisters a credible British accent and convince a generation that she’s actually a twin.

A remake of the 1961 Parent Trap that starred Hayley Mills, an earlier Disney star, the film is a bit too casual about explaining how these girls, Hallie and Annie, have never been aware of each other’s existence (one was raised in Napa by Dennis Quaid, the other in London by Natasha Richardson).

Surely if you met your identical twin you’d want to get to the bottom of the conundrum immediately. Hallie and Annie are too busy being spit-image camp rivals. But who cares? Lohan is a natural as an actress, not in the least precocious or precious. She’s funny, spontaneous and, considering the setup, believable.

What gives the movie its prominence here is that it’s also directed by Nancy Myers, who would go on to please audiences with two terrific Diane Keaton comedies, Baby Boom and Something’s Gotta Give. Myers has a fine eye — the film has a look of polished, tasteful, unobtrusive affluence — and an assured sense of comedy: She brings out a fizzy, glamorous sense of fun in Richardson. 

The Parent Trap is available on Disney+.

2. Mean Girls (2004). This slick, funny high-school satire is probably the Lohan movie with the strongest, most enduring cross-generational appeal. It certainly has the cleverest script, written by the sharp and savvy Tina Fey, who also plays a teacher.

You can argue that Mean Girls, based on a nonfiction book with the galloping title Queen Bees and Wannabes: Helping Your Daughter Survive Cliques, Gossip, Boyfriends, and Other Realities of Adolescence, isn’t as clever as it thinks it is — Election (1999), young Reese Witherspoon’s finest hour, is the punchier takedown of high-school culture — but that’s neither here nor there. You’ll have a hard time not enjoying a movie that features Amy Poehler as a “cool mom” or lines that include “I gave him everything! I was half a virgin when we met.”

Lohan is actually at something of a disadvantage here, though. She has the star’s part — Cady, a naive, formerly homeschooled student at sea in American adolescence — but hers is essentially a straight role, and she’s surrounded by a cast of skillful actresses who deliver Fey’s jokes not only with the requisite sting, but also a surprising amount of insight and nuance.

Rachel McAdams, as Regina, the meanest of the revered, terrifying “Plastics,” even wins a certain amount of sympathy, slipping toward dysmorphic pathos as Cady gets the upper hand. Lohan is glowingly beautiful — that glow has been everything to her career — but she rushes through the escalating complications with a kind of frantic breathlessness, a huffiness, that at times undercuts the beguiling huskiness of her voice. I’d like to have seen her and McAdams switch roles, like the girls in The Parent Trap.

Lohan also turns up in 2024’s obnoxious movie-musical reboot as the ref of a debate competition. She has one very fine line that strikes a possibly self-referential note of sadder-but-wiser experience: “Honey, I don’t know your life.”

Mean Girls is available on Paramount+.

3. The Canyons (2013). Directed by Paul Schrader with a script by Bret Easton Ellis, this spiritually bleak L.A. drama features Lohan’s most daring performance, and probably the only one that manages to break completely with her childhood and adolescent roles.

She plays Tara, a woman who seems to have surrendered any control — moral or physical — over her life. She’s kept by a snotty movie producer, Christian (adult film star James Deen), who has a reputation for violence and expects her to participate in small orgies in his cold, modern box of a house. Tara finally breaks free of him — that’s the crux of the drama — but in a near-tragic sense she remains trapped. Her existence will always be dictated by someone else’s will. 

Lohan’s behavior during the low-budget production generated press reports and controversy, some of it puzzling. According to TMZ, she wanted the crew to drop trou when it came time for her to shoot a crucial nude scene (director Schrader, at least, obliged her).

Regardless, Lohan delivers a powerful, complex performance — memorably fierce and desperately raw, at times combative yet fundamentally passive. The Canyons isn’t an especially likable film—the artistically ambitious Schrader, as a rule, isn’t happy unless you’re unhappy — but it proves just how good an actress Lohan can be.

The Canyons is available on Prime Video.

4. Freaky Friday (2003). Author Mary Rogers, in her memoir Shy, remembered how she was inspired to write the YA novel that became, first, a popular 1976 film with Jody Foster and then this canonical Lohan hit.

Looking back at her time raising two teen daughters, Rogers wrote, “Sometimes I wanted to kill them and sometimes I wanted to be them. I imagine they felt the same way about me, because however much better a time they were having than I’d had, and despite my nutso liberal ways, I was still, to my astonishment, an authority figure. How had I become my own mother?”

From Rogers’ perspective then, this tale of a body-swapping mother and daughter is conceptually and emotionally, as well as comically, weighted more toward the mother, Tess (Jamie Lee Curtis), than the daughter, Anna (Lohan).

To an audience, the result can be a bit like watching an earlier version of Mean Girls. Jamie Lee Curtis is rewarded the lion’s share of funny material: Tess-inhabited-by-Anna is a giddy woman-child, trying to make sense of adult therapy patients, appearing on TV to promote a book she doesn’t understand (it has the word “senescence” in the title) and being flirted with by teenage dreamboat Jake (Chad Michael Murray).

As Anna-inhabited-by-Tess, Lohan is stuck playing a corporeally maladroit scold. But it’s a game performance. You can see that Lohan, coming into her own fresh, girlish beauty at 16, was already a star.

Freaky Friday is available on Disney+.

5. A Prairie Home Companion (2006). Director Robert Altman’s last film, A Prairie Home Companion would go higher up on this list if Lohan’s role wasn’t relatively small, but she holds her own in an ensemble that includes Meryl Streep (who plays her mom), Lily Tomlin, Kevin Kline, Tommy Lee Jones, Maya Rudolph and Woody Harrelson, as well as writer-performer Garrison Keillor, who hosted the genial, whimsical Prairie for decades on the radio. It’s Keillor’s script, as well.

This is a funny but moving comedy that imagines the Companion’s very last night where an out-of-town conglomerate — represented by the complacently heartless Jones — has bought the theater and has no interest in letting the show continue.

Lohan, wearing glasses, with her hair hanging down in straight curtains, plays a would-be poet with a morbid streak. Her latest dramatic creation, Soliloquy for a Blue Guitar, begins: “Death is easy, like jumping into the big blue air and waving hello to God / God is love, but He doesn’t necessarily drop everything to catch you, does He?”

Eventually, though, she catches the spirit of the place, the show and the performers, and throws herself into singing the old torch ballad “Frankie and Johnny,” supplemented with nonsense lyrics.

The movie, which is very much about the encroaching shadow of death, needs Lohan’s youth — she’s springtime to its autumn.

A Prairie Home Companion is available on Tubi.

6. Confessions of a Teenage Drama Queen (2004). It might be enough to say that Lohan is perfectly bright and cute in this teen comedy and move on. But Confessions was Lohan’s third feature film for Disney, and she’d become enough of a star that she was cast in what might be called Lohanian vehicles — where her films were not only tailored to what she’s expected to do, but also play to her strengths as a star.

Lohan plays Mary, a Manhattan girl who’s miserable when her mom relocates the family to New Jersey. That, to Mary, is the kiss of death. Still, she manages to find somewhat of a silver lining as this blighted bland suburb allows her to indulge a talent for the flamboyant gesture: She christens herself Lola, lands the role of Eliza in her school’s updated production of Pygmalion (with songs!) and mourns the breakup of her favorite band, Sidarthur, as if she were Queen Victoria grieving for her Albert.

But Lohan doesn’t really convince you that she’s a wild young romantic vibrating with fantasies that may collide with reality. It’s not that you want a kid version of Katharine Hepburn in Stage Door, murmuring about calla lilies, or (heaven forbid!), Liza Minnelli in Cabaret. But Lohan isn’t madcap, campy or impulsive. She seems to already own the world.

Her performance does finally catches fire in a big, silly musical number at the end.

Confessions of a Teenage Drama Queen is available on Disney+.

7. Falling for Christmas (2022). After stepping away from the movie business for a period, Lohan landed on a secure perch with a string of Netflix movies, starting with this holiday romcom. Falling for Christmas doesn’t make any more or less sense than most productions of this sort, so the plot isn’t something to worry about.

In the film, Lohan plays Sierra, the cosseted daughter of a hotel magnate. She’s completely lacking in any domestic skills — when she tries to make a bed, the sheets end up cocooning her — and she doesn’t object if one of her father’s minions holds a flute of champagne to her lips while she works her way through a rack of designer clothes.

When Sienna’s insipid influencer boyfriend (George Young) lures her up onto a remote, snowy peak to propose marriage, she loses her balance and rolls and thumps her way down to level ground. Waking up in the hospital with no memory, she’s entrusted to the care of Jake (Chord Overstreet), the man who found her.

He takes her home to his rustic inn — a far cry from Daddy’s five-star establishments — where she sheds her pampered shallowness.

Lohan is very funny as the spoiled-brat Sierra and radiant as the amnesiac one. The movie exists solely so she make a grand but humble appearance in an unpretentious dress of bright Christmas red. In other words, Lohan delivers exactly the performance Falling for Christmas requires. There’s not much you can do about her lack of chemistry with Overstreet or Young. They’re not the ones you’re supposed to be falling for, anyway. 

Falling for Christmas is available on Netflix.

8. Machete (2010).  Lohan’s role in director Robert Rodriguez’s pulpy, violent action fantasy is very small — she’s named April and spends much of the movie unconscious in a rectory.

With an enormous mane of golden blonde hair and not much clothing, she could be a Playboy bunny or a 1970s shampoo model. But Rodriguez understands the potency of Lohan’s iconic status:  When the bloody mayhem is at its most explosive, she comes into camera range, dressed as a nun and carrying a shotgun aimed at a vile politician (none other than Robert De Niro).

As you probably guessed, this is a strange, wild movie, with a cast that includes Danny Torres (as the machete-wielding hero), Jessica Alba, Cheech Marin and Don Johnson. But Machete is also a still-timely political allegory about a monstrous conspiracy targeting Mexican immigrants.

Lohan is a sort of avenging angel, only more avenging than angelic.

Machete is available on Hulu.

9. Liz & Dick (2012). It’s not surprising that Lohan should identify with Elizabeth Taylor. A former child star, she claimed she couldn’t remember a time when she wasn’t famous. But the grownup Taylor was volcanically erotic (think of her passion as the hottest of lavas!) and so sure of her star power that she didn’t worry about the shocking vicissitudes of her personal life. 

If Taylor could be sublimely vulgar, as well as sublimely sexy, that was all part of what made her such an irresistible presence on screen. The camera worshiped her. Lohan, you might say, it merely loves. 

In this Lifetime movie she bravely tries to play Taylor during her heady years with actor Richard Burton (Grant Bowler) — the pair enjoyed each other with such concupiscent gusto, they were denounced by the Vatican for “erotic vagrancy.”

Lohan’s performance, though, is a miss. She cries very prettily, smiling through heartbreak, but she doesn’t have anything like Taylor’s propulsive, sweeping, get-outta-my-way force. Helena Bonham Carter comes much closer to Taylor — boozy, reckless and yearning — in the 2013 BBC movie Taylor & Burton.

Liz & Dick is available on Prime Video.

10. Georgia Rule (2007). Directed by Garry Marshall, this comedy drama has a riveting, deeply ambiguous scene that can be considered a kind of acting triumph for Lohan, who plays a troubled young woman, Rachel, spending the summer with her stern grandmother (Jane Fonda). When Rachel puts the moves on a local boy (Garrett Hedlund), her eyes flash with a kind of carnal appreciation — but for just a second. Then her expression darkens to suggest some deeper emotional doubt or reluctance.

But even with that moment — and a prestigious cast that includes Felicity Huffman and Dermot Mulroney — Georgia Rule was problematic for Lohan. During production, a studio executive sent her a letter chiding her for unprofessional conduct. (“We are well aware that your ongoing all night heavy partying is the real reason for your so-called ‘exhaustion,'” wrote James G. Robinson, who also accused Lohan of costing the production “hundreds of thousands of dollars in damage.”) And then the movie was released to cruel reviews. Poison pens, all around.

Eighteen years on, Georgia can be appreciated for all its performances. Fonda fires off her lines with clipped gruffness, and Huffman suffers a startlingly realistic physical collapse.

But it is a terrible movie. What begins as a genial, possibly sentimental coming-of-age tale turns out to harbor a wormy heart, infested with dysfunction and abuse deep. Yet, Marshall seems unwilling to let go of that genial sentimentality. He’s like a man who’s been staring up a chimney for years, face covered with soot, hoping that Santa will finally come down. 

The tone grows so off-putting you just sit there, shaking your head. Nor does the movie seem to understand how destructive, manipulative and dishonest Rachel can be. This could have been Lohan’s Hedda Gabler. And that would have been something.

Georgia Rule is available on Hulu.