26. Casey Stuart in Life-Size (2000)
Is there anything sadder than a child who is so lonely that her only friend is a doll? This could’ve turned out way differently, like horror movie differently, but instead it’s a psychological drama disguised as a family comedy. But we digress.
Lohan plays the perfect outcast. The only girl on the football team—the quarterback, no less—she’s argumentative and suppresses some deep-seated depression that she takes out in a bizarre way. Her mom just kicked the bucket, so she dabbles with a book of the dark arts to bring her mom back to life. It fails. The doll comes to life instead. It’s completely believable why she only has one friend. —TA
25. Ashley Albright in Just My Luck (2006)
In her first non-teen role, as the lucky until love character Ashley, critics were still on Lohan’s side. Just My Luck didn’t earn a lot of praise, but people were coming to Lohan’s defense. The movie itself failed to show Lohan’s charm. The Razzie awards were less kind—Lohan earned herself Worst Actress for her role. —TA
24. Elizabeth Taylor in Liz & Dick (2012)
Poor Lindsay Lohan—this film was her first movie to came out after she took a little acting hiatus, and it wasn’t even on the big screen. It’s hard to watch because you spend so much of the movie laughing. Who can follow a story through that many giggles? Her face barely moved, so it was tough to say if she was fully awake for the entire performance. Even her most dramatic scenes were hard to latch onto. We have to give her some credit by trying to get herself back into the game, though. —VC
23. Danielle in That ’70s Show (2004)
Fez was the butt of everyone’s joke on That 70’s Show for many reasons, but definitely because he failed miserably at getting laid. Some people forget, but he actually got to canoodle with the then-redhead Lindsay Lohan after he gave her a heavenly head massage.
Like most guest appearances, she was playing the “Look! it’s Lindsay Lohan making a guest apperance!” role more than she was trying to portray a character. We were mostly glad that Fez got to release some of his sexual tension with this babe. They actually dated off-screen as well. —VC
22. Thea Clayhill in Labor Pains (2009)
No better to way to put it: Labor Pains is a bad, bad movie. Lohan plays a woman who fakes a pregnancy because it turns out that everyone around her treats her better when she’s with child. Highlights include a scene where she scraps with family and friends over the fake belly she’s been wearing. Lohan phones everything in, and you would do well to stay far, far away from this. —RS
21. Rachel Wilcox in Georgia Rule (2007)
Maybe Georgia Rule wasn’t the best career choice for Lohan. The film is often called “Lohan’s Gigli” and “a sitcom about sexual abuse,” which, well, sounds horrible. But Lohan’s character Rachel, who has sex with the Mormon boys and swears at her entire family throughout the film, isn’t the only unlikeable part of the whole production. There seemed to be more than enough discomfort on screen between Lohan and the movie’s other stars (Felicity Huffman, Jane Fonda), and we don’t think it can all be attributed to brilliant acting. On top of that, Lohan, just shy of being 21 years old, was well known for her own party girl attitude and the infamous letter from the CEO of Morgan Creek Productions about her allegedly unprofessional behavior while filming. —TA
20. Mary Elizabeth “Lola” Cep in Confessions of a Teenage Drama Queen (2004)
This musical movie is a mess, despite the fact that it earned a healthy spot as the number two movie at the box office when it was released. It’s really because Lohan’s character is a huge hot mess, and she plays it accordingly. She lies about her father dying to make friends. Who really thinks that’s a good idea? Psychopaths. Sorry you had to move away from New York City to New Jersey, but that is not a healthy way to get people to pay attention to you at school. —TA
19. Marilyn in InAPPropriate Comedy (2013)
Oh, Mr. ShamWow Guy (government name: Vince Offer). That shameless, talentless hack. In his unbelievably bad spoof comedy InAPPropriate Comedy, Offer’s peak of cleverness is having Lindsay Lohan dress up as Marilyn Monroe and fire machine guns at paparazzi. Why? Because it’s “provocative.” Of course, it’s also just as on-the-nose as everything else in the film, like Adrien Brody’s Dirty Harry rip-off of a character using the catchphrase, “Go ahead, make me gay.”
Lohan’s work in InAPPropriate Comedy doesn’t qualify as acting. It’s desperate self-parody, and it’s not at all funny. —MB
18. Maggie Peyton in Herbie: Fully Loaded (2005)
Lindsay Lohan is, once again, given the role of an adorable teenage girl. Essentially, she has to save her family from financial dangers by racing a magical old buggy. She raises her eyebrows, makes snarky adolescent comments, and has a mediocre romance with the geeky Justin Long. It’s nice to see Lindsay when she was wholesome, but her acting chops were barely there. The animated car might have stolen the show. —VC
17. Alli Fowler in Another World (1996-1997)
Not much to say here. Lohan was 10. She had the charm of a 10-year-old who felt comfortable in front of a camera on the set of a soap opera. She smiled in the correct ways. She stood out because of her red hair. People took notice—including Disney. It was just a year later that she would make her big splash in The Parent Trap.
16. Jenny Medina in King of the Hill (2004)
Lohan provided the voice for Jenny Medina on a single episode of King of the Hill entitled “Talking Shop.” The episode finds Bobby obsessing over dating. Lucky guy, he ends up with Jenny Medina. The episode was released in 2004, the same year as Mean Girls, and Lohan’s smoky voice was unmistakable. Be still, young Bobby. Don’t blow it.
But, of course, he does. —RS
15. April Booth in Machete (2010)
It wouldn’t be fair to evaluate the performances in Machete as either “good” or “bad.” Save for leading man Danny Trejo, who’s a spot-on badass throughout, the rogue’s gallery of recognizable actors (Robert De Niro, Don Johnson, Steven Seagal) playing exaggerated, flesh-and-blood cartoon characters in Robert Rodriguez’s tongue-in-cheek, sleazy exploitation throwback are all operating on their most purposefully ridiculous levels.
Take Lohan, for instance. She plays April Booth, the daughter of Machete’s enemy who, along with her equally naked (though, reportedly, Lohan’s nipples, as seen in the film, aren’t actually Lohan’s nipples) and buxom mother, makes a DIY skin flick with the Mexican ass-kicker. All Lohan’s asked to do is look hot (check), pretend to woozily wake up from a long night of crazy sex (convincing enough), and bust guns while wearing a nun’s outfit (agreeably campy). Mission accomplished. —MB
14. Herself in Glee (2010)
Of course there’d be a few jokes at Lohan’s expense on Glee. She plays herself as a celebrity judge during a glee club competition, and her reputation isn’t ignored. That said, her attempt to “rebrand” herself doesn’t go as smoothly as planned. Drama on the set was all over the entertainment news cycle and Twitter. Allegedly, Lohan was three hours late on her second shoot date and didn’t memorize her lines. But maybe that’s all gossip, as no one can get their story straight. Some sources say she was six hours late, some sources say she just got stuck in hair and makeup for too long. —TA
13. Diane Howser in Bobby (2006)
Bobby follows the lives of various people—rich, poor, young, old, black, white—on the day leading up to the assassination of Senator Robert F. Kennedy on June 5th, 1968. Lindsay Lohan and Elijah Wood are Diane Howser and William Avary, just friends. However, their platonic relationship changes when Diane agrees to marry William in the hopes that he won’t be sent to Vietnam, as the threat of a full-out war looms in the near-future. What started as a possible life-saving favor for a friend turns into the real deal.
Diane ultimately confesses her true feelings of love to William and the two approach the idea of their wedding with completely new perspective. Lohan and Wood are joined by other great actors in this film, including Harry Belafonte, Laurence Fishburne, Anthony Hopkins, Helen Hunt, Ashton Kutcher, Shia LaBeouf, Demi Moore, Christian Slater, and Sharon Stone. —SS
12. Jude Hanson in Chapter 27 (2007)
Chapter 27 received conflicting reviews when upon its release, and was considered to be one of the most controversial films of 2007. Of course, this was primarily due to the content, which attempts to portray the emotional instability of Mark David Chapman (played by Jared Leto) in the days leading up to the murder of John Lennon. Lohan portrays Jude, a likeable Lennon fangirl who befriends Chapman and provides him with the knowledge that helps him to gain such close access to Lennon and his family. Although she only has a small part in this film, Lohan’s charisma earned her some favorable looks. —SS
11. Lola Johnson in A Prairie Home Companion (2006)
Lohan plays Lola Johnson, the daughter of the somewhat feisty, charismatic Yolanda Johnson (Meryl Streep), a country singer on the rather antiquated live radio show, A Prairie Home Companion. The radio show consumes their lives, making the cast into a family of misfits.
Lola is an angsty, song-writing teenager and parts of the movie explore her dynamic, kind-of-dysfunctional relationship with her mother Yolanda. As the two strive to understand each other and reconcile their conflicting viewpoints and ideas, you can feel Streeps skills making Lohan better. —SS
10. Lexy Gold in Get a Clue (2002)
In the final film of Lohan’s three-picture deal with Disney, Get a Clue, Lohan’s character Lexy runs her Manhattan school newspaper’s gossip column, which is a nice taste of irony, as she’s been a staple in every piece of tabloid trash since. It’s a lighthearted, comedic high school romp-until her teacher goes missing, his car is found in the East River, and Lohan’s character figures she’s the perfect person to solve a murder case. Unsurprisingly, Lohan does a convincing job with dark material. —TA
9. Herself in Scary MoVie (2013)
Faint praise alert. In a spoof movie that’s as out of date as it is unfunny, Lindsay Lohan’s one of the only worthwhile participants. Sure, her self-mocking scene with similar controversy magnet Charlie Sheen would’ve been funnier two years ago, when people actually cared about Charlie Sheen’s antics, but at least she and the former Tiger Blood champ have some chemistry. They both also seem to be enjoying the otherwise uninspired lampooning, which is shot found-footage sex tape style and aims to send-up the Paranormal Activity movies. Even though the only buffoons who’d find their Scary Movie 5 scene funny are their agents, Lohan and Sheen’s playful work together is ultimately harmless. —MB
8. Aubrey Fleming and Dakota Moss in I Know Who Killed Me (2007)
In I Know Who Killed Me, Lohan plays a stripper who’s being stalked by a gruesome serial killer—what’s not to love? Try a script that’s intended to evoke David Lynchian psychosis but conjures up nothing more than uproarious laughter and tireless head-scratching. Add a director, Chris Sivertson, who’s clearly seen Dario Argento’s Suspiria one too many times, drowning every scene in overdone, loud blue and red color palettes.
Yet, putting all of that negativity aside, I Know Who Killed Me has the kind of entertainment value that most directors of Academy Award hopefuls could only wish to achieve. Give the beleaguered Lohan credit, too, because her performance here, playing enigmatic twins on a homicidal maniac’s to-slaughter list, is nothing if not go-for-broke.
That doesn’t make her performance any good, of course—most of the time, she’s either writhing on a stripper pole (minus any titillation) or enduring gratuitous, overlong torture (minus any sympathy or effective tension). It’s a whole lot of self-degradation for nothing but scathing reviews. —MB
7. Rose Midler in Bette (2000)
Lohan appears in the pilot episode of the TV show Bette as Bette’s confident, young daughter Rose. In one of the scenes, Rose introduces her boyfriend to Bette and he seems to be more enraptured by the mother rather than the daughter, which no doubt leads to some trouble on the mother-daughter side of things. There was trouble behind the scenes, as well. Bette Midler decided to shoot the show in L.A. instead of NYC, forcing the 14-year-old Lohan to drop out. Too bad, because she was pretty good. —SS
6. Kimmie Keegan in Ugly Betty (2008)
Lohan plays Kimmie, America Ferreira’s bully since middle school on Ugly Betty. She channels more emotion here playing a mean backstabber than in most of her other projects. It’s too bad that Ugly Betty was canceled because that was definitely a role she could come back to. —VC
5. Herself in Anger Management (2013)
This time Lohan was allowed to play herself. It was nice to find that she was a good sport about making fun of herself. Perhaps it helped to be working with an actor that’s also gotten a lot of shit from the media. It’s a bit disconcerting to watch her and Charlie Sheen make out considering their age and personal backgrounds, but it’s all for show, right? —VC
4. Tara in The Canyons (2013)
Everyone prepared for The Canyons to be a disaster? Disappointed. Everyone prepared for The Canyons to be a surprise success? Disappointed.
The sad truth is that Paul Schrader’s Kickstarter-funded L.A. picture is Bret Easton Ellis by the numbers, right down to the dull sex and “sudden” violence. It isn’t particularly Brechtian; it’s just old hat. That said, Lindsay Lohan is low-key captivating. Those puffy cheeks and dark eyes exhibit shame and embarressment. They cry real tears. Everyone else in the film is so wooden—word to James Deen’s dick—and shark-eyed, but Lohan feels alive. —RS
3. Hallie Perkins and Annie James in The Parent Trap (1998)
When The Parent Trap came out, people couldn’t believe that there was only one Lindsay Lohan. In fact, we still don’t believe it. The acting was too good for a child with presumably no life experience whatsoever. How could she possibly portray completely different girls? Obviously, the evil twin Lohan destroyed the good twin, absorbed her power, and tarnished her name. But, regardless, we totally thought Lohan was going to be the next great actress. She showed so much promise in this Disney film. —TA
2. Anna and Tess Coleman in Freaky Friday (2003)
She wears a plaid skirt, has a crush on a boy with a motorcycle, and she’s in a rock band? We should have seen the warning signs. Lohan officially entered her rebellious teen years in Freaky Friday, and she played it with pitch perfect angst.
Fortunately, in the film, she switches bodies with her mother (Jamie Lee Curtis) so they can finally see eye-to-eye about what’s bothering each of them. That is, how Lohan’s character, Anna, isn’t ready to accept her mom’s new fiance three years after her father’s death and how her mother doesn’t understand her daughter’s love of rock ‘n’ roll. Unfortunately, Lohan didn’t get to switch bodies with her real life mom to make her realize how awkward it is when you see your own mom at the clubs you’re going to. —TA
1. Cady Heron in Mean Girls (2004)
Yes, it is common knowledge that Lohan read for the “mean girl” part (Regina George, which went to Rachel McAdams) in one of the greatest teen comedies ever written, but she felt that it would hurt her reputation. Which is ironic, considering her career trajectory after the movie.
Mean Girls is Lohan’s peak. It’s regarded as her best film, and she’s flawless as Cady, the innocent good girl from Africa who gets mixed up with the wrong crowd. It was an undoubtable indication that Lohan was well on her way to a very exciting, award-winning career. But then real life began to interfere with her acting, and her personal business became much more interesting to the general public than her subsequent films. And that’s how we got The Canyons.