Lindsay Lohan's top 20 movie roles, ranked from worst to best

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Ignacio Weil

Entertainment - December 10th 2024, 18:30 GMT+1

Cropped About — About this gallery:

For this list, we have decided to focus only on movies where Lindsay Lohan appears, no matter how small her role is. For this reason, don’t expect any of her performances in series, short films, or commercials. And remember, this list is subjective! If you think any movie is not in the right spot, share your opinion!

| © Lindsay Lohan

Cropped I Know Who Killed Me — 20. I Know Who Killed Me (2007)

Oh, *I Know Who Killed Me*. This movie is like a B-movie fever dream wrapped in a psychological thriller that tries way too hard to be edgy. Lindsay Lohan plays dual roles as a small-town girl and her "mysterious" doppelgänger, and while her commitment is commendable, the script is so absurd it derails any serious attempt at drama. Featuring stripper poles, a blue aesthetic that no one asked for, and a plot twist that feels more like a head-scratch, this film is less of a thriller and more of an unintentional comedy. At least Lohan gave it her all – it’s not her fault the movie’s logic checked out early. | © TriStar Pictures

Cropped Chapter 27 — 19. Chapter 27 (2007)

Here, Lohan takes on a supporting role opposite Jared Leto, who gained significant weight to play Mark David Chapman, the man who assassinated John Lennon. Unfortunately, the film feels as heavy as its lead actor’s transformation. Lohan plays a Beatle-obsessed fan who crosses paths with Chapman, but her character is underwritten and largely forgettable. It’s as if the filmmakers needed to throw in a recognizable face but didn’t know what to do with her. The movie's sluggish pacing and overly self-serious tone don’t do Lohan – or anyone – any favors. At least the concept was ambitious? | © Peace Arch Entertainment

Cropped Bobby — 18. Bobby (2006)

Unlike some of the more questionable entries on this list, *Bobby* has the bones of a good film. It’s an ensemble drama chronicling the hours leading up to Robert F. Kennedy’s assassination, and Lohan plays a young woman marrying a man to keep him from being drafted. While her performance isn’t bad, the sheer number of characters means her role feels more like a cameo than a proper arc. *Bobby* has its poignant moments but struggles to give every story the weight it deserves. Still, it’s nice to see Lohan as part of a more serious project. | © The Weinstein Company

Cropped Our Little Secret — 17. Our Little Secret (2024)

This one’s fresh off the press – or maybe still in the printer. *Our Little Secret* marks Lohan’s attempt to step back into the spotlight with a psychological drama. While the plot (centered around a family’s buried skeletons) is intriguing on paper, the execution is a little uneven. Lohan is compelling in moments, but the film often feels unsure of whether it wants to be a tense mystery or a melodrama. It’s not a bad movie, but it’s not quite the comeback one might hope for either. | © Independent Production

Cropped Liz Dick — 16. Liz & Dick (2012)

Oh, the infamous *Liz & Dick*! A Lifetime movie that was supposed to relaunch Lohan as a serious actress but instead became meme fodder. Lohan plays Elizabeth Taylor, and while she looks the part in some scenes, the performance is uneven, and the melodramatic dialogue doesn’t help. The film’s low-budget feel and over-the-top tone make it hard to take seriously, but there’s a campy charm to its sheer audacity. If nothing else, Lohan gave it her all – and hey, it’s a fun watch with a glass of wine. | © Lifetime Network

Cropped Irish Wish — 15. Irish Wish (2024)

Lindsay Lohan heads to Ireland in this Netflix rom-com that feels more like a Hallmark movie on a caffeine high. Playing a woman who wishes for a different life after her crush gets engaged to someone else, Lohan embraces the role with her trademark charisma. Unfortunately, the plot relies too heavily on clichés, and the charm of the Irish setting isn’t enough to carry the film. There are some fun moments and heartfelt touches, but the movie never quite finds its footing. Lohan is clearly trying to recapture her rom-com magic here – maybe next time the script will meet her halfway. | © Netflix

Cropped Labor Pains — 14. Labor Pains (2009)

Pretending to be pregnant to keep a job is, admittedly, a bonkers premise, but *Labor Pains* leans into its absurdity, and Lohan does her best to make it work. As a secretary desperate to avoid being fired, she delivers a performance that’s light and cheeky, even if the script is about as deep as a puddle. The movie isn’t exactly memorable, but it’s got enough quirky humor and slapstick moments to keep things entertaining. Think of it as a guilty pleasure, perfect for a lazy Sunday when you’re in the mood for something silly. | © Nu Image

Cropped The Canyons — 13. The Canyons (2013)

Oh, *The Canyons*. This experimental neo-noir thriller aimed for edgy and ended up somewhere between awkward and unintentionally hilarious. Lohan stars as a disillusioned actress caught in a toxic web of lies and manipulation, and while she gives a brave performance, the wooden dialogue and awkward pacing drag her down. The real star of the film might be its own chaotic vibe – complete with an adult film actor in a lead role and a script by Bret Easton Ellis. Love it or hate it, it’s hard to deny that this movie is an experience. | © IFC Films

Cropped Life Size — 12. Life-Size (2000)

A doll that comes to life and teaches life lessons? Sign us up. *Life-Size* is the kind of goofy, feel-good Disney movie that only works if everyone involved fully commits – and thankfully, Lohan and Tyra Banks absolutely do. Lohan plays a grieving young girl who accidentally brings her fashion doll, Eve, to life, and their dynamic is the heart of the film. It’s cheesy, sure, but it’s also brimming with nostalgia and charm. If you grew up with this movie, there’s a good chance you still know the words to “Be a Star.” Shine bright, Lindsay! | © Disney Channel

Cropped Get a Clue — 11. Get a Clue (2002)

This Disney Channel original movie is a time capsule of early 2000s tween culture – complete with terrible fashion and a mystery plot straight out of a kids’ detective series. Lohan plays Lexy Gold, a privileged teenager-turned-sleuth, and she brings plenty of spunk to the role. The story itself is pretty basic, and the tech feels hilariously outdated today, but that’s all part of the fun. Watching this now is like diving into a scrapbook of simpler times when everything was neon, and flip phones were cutting-edge. Not groundbreaking, but undeniably entertaining. | © Disney Channel

Cropped Georgia Rule — 10. Georgia Rule (2007)

Lindsay Lohan stars alongside Hollywood heavyweights Jane Fonda and Felicity Huffman in this dramedy about three generations of women navigating family dysfunction. The film tackles heavy subjects but struggles to balance its darker moments with its attempts at humor, leaving the tone uneven. Lohan’s performance as a rebellious teenager is solid, showing flashes of the dramatic chops she’s capable of. However, the script often veers into melodrama, making it hard to fully connect with the story. Still, there’s something compelling about watching Lohan hold her own with such a seasoned cast. | © Universal Pictures

Cropped Machete — 9. Machete (2010)

Robert Rodriguez’s grindhouse action flick is an over-the-top, blood-soaked ride, and Lindsay Lohan’s small role as a troubled party girl (a nun costume is involved) adds an extra layer of camp to the chaos. While she isn’t the focus, her character is a memorable part of the film’s wild tapestry. It’s clear Lohan is having fun here, leaning into the absurdity with tongue firmly in cheek. This is not a movie for subtlety or nuance, but as far as cameo-like roles go, it’s a blast to watch her embrace the madness. | © 20th Century Fox

Cropped A Prairie Home Companion — 8. A Prairie Home Companion (2006)

In this ensemble comedy-drama, Lohan steps into a more understated role as a poetically inclined teen in a movie about the fictional final broadcast of a beloved radio show. Directed by Robert Altman and boasting a stellar cast (Meryl Streep, Lily Tomlin, and Kevin Kline, to name a few), the film oozes charm and melancholy. Lohan fits right in, delivering a subdued but effective performance that hints at her potential in quieter, more character-driven stories. It’s a nice change of pace from her usual roles, proving she can hold her own in a prestigious ensemble. | © Picturehouse

Cropped Herbie Fully Loaded — 7. Herbie: Fully Loaded (2005)

Revving up the nostalgia, *Herbie: Fully Loaded* brings back everyone’s favorite anthropomorphic VW Beetle with a modern twist. Lohan plays Maggie, a spunky racer who discovers Herbie’s quirky personality and hidden talents. It’s a fun, family-friendly romp with plenty of heart, and Lohan’s charisma is the engine that keeps the movie moving. Sure, it’s formulaic, but it’s also undeniably charming, and her chemistry with the car (yes, the car) is oddly endearing. A solid pick for a feel-good movie night. | © Walt Disney Pictures

Cropped Just My Luck — 6. Just My Luck (2006)

A rom-com about trading fortunes through a kiss? Count us in! Lohan stars as Ashley, a perpetually lucky woman whose life turns upside down when she swaps her charmed existence with a perpetually unlucky musician. The premise is delightfully ridiculous, and while the movie doesn’t reinvent the wheel, it’s a breezy, enjoyable watch. Lohan’s comedic timing and natural charm shine, making her the perfect lead for this kind of lighthearted fare. It’s not her most groundbreaking work, but it’s a reminder of why she became a rom-com favorite in the first place. | © 20th Century Fox

Cropped Falling for Christmas — 5. Falling For Christmas (2022)

Lindsay Lohan’s return to leading roles in this Netflix holiday rom-com is like a warm cup of cocoa – predictable, comforting, and a little cheesy. She plays a spoiled hotel heiress who loses her memory and ends up falling for a small-town widower (because of course she does). The movie leans into every holiday trope imaginable, but Lohan’s charm makes it work. Her comedic timing and genuine warmth shine, reminding fans why she’s a star worth rooting for. It’s not groundbreaking cinema, but it’s a feel-good comeback for Lohan that hits all the cozy, festive notes. | © Netflix

Cropped Confessions of a Teenage Drama Queen — 4. Confessions of a Teenage Drama Queen (2004)

In this underrated teen comedy, Lohan steps into the spotlight as Lola, a theatrical high schooler with big dreams of stardom. The film is a colorful, exaggerated ode to teenage ambition and self-discovery, and Lohan brings boundless energy and charisma to the role. While the story is predictable, it’s packed with enough quirky humor and heartfelt moments to keep things engaging. The over-the-top fashion and musical numbers make it a time capsule of early 2000s teen culture, and Lohan’s magnetic performance ties it all together. | © Walt Disney Pictures

Cropped Freaky Friday — 3. Freaky Friday (2003)

Switching bodies with your mom? Hilarious chaos ensues! Lohan stars alongside Jamie Lee Curtis in this delightful family comedy, and their chemistry is pure magic. Lohan nails the comedic beats and brings a grounded warmth to her role, balancing teenage angst with newfound adult wisdom. The film’s sharp humor and heartfelt message about empathy and understanding make it a standout in her career. Plus, who doesn’t love the garage band finale? This one still holds up as a crowd-pleaser for all ages. | © Walt Disney Pictures

Cropped The Parent Trap — 2. The Parent Trap (1998)

Lindsay Lohan burst onto the scene in this beloved remake, playing not one but two roles as twins separated at birth who scheme to reunite their parents. At just 11 years old, Lohan showcased incredible range and charisma, seamlessly switching between the posh Annie and the mischievous Hallie. The movie is brimming with heart, humor, and unforgettable moments (who can forget the Oreos and peanut butter scene?). It’s no wonder this performance launched her into stardom – Lohan carries the film with the confidence of a seasoned pro. | © Walt Disney Pictures

Cropped Mean Girls — 1. Mean Girls (2004)

Is there a more iconic teen movie? *Mean Girls* isn’t just a film; it’s a cultural phenomenon, and Lindsay Lohan’s portrayal of Cady Heron is a big reason why. From her wide-eyed innocence to her Queen Bee takedown, Lohan brings nuance and humor to a role that could’ve been one-note in less capable hands. The sharp, endlessly quotable script by Tina Fey is perfectly matched by Lohan’s ability to handle both comedy and heartfelt moments with ease. *Mean Girls* solidified Lohan’s status as a teen icon and remains her crown jewel – totally fetch. | © Paramount Pictures

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Lindsay Lohan has long been a fixture in Hollywood, captivating audiences with her charm, talent, and versatility. From her early days as a Disney darling to her more mature and complex performances, Lohan has built a filmography that is as fascinating as it is diverse. With standout hits, cult classics, and even a few missteps along the way, her career has been a rollercoaster ride that mirrors her larger-than-life persona.

In this ranking, we dive into her top 20 movie roles, charting her growth as an actress and the unforgettable characters she brought to life. Whether you're a die-hard fan or revisiting her work with fresh eyes, this list celebrates the highs and lows of a star who has left an indelible mark on pop culture. Let’s count down from her most forgettable roles to her career-defining performances.