It's 2022 and Lindsay Lohan has just signed a 2-picture deal with Netflix. With the surging popularity of early 2000s pop culture, is the trend-setting teen queen of the era finally ready to take back her crown?Turbulent personal life aside, Lohan has a solid track record for starring in hit movies. She reigned box office supreme from 2003 to 2005, but the immense pressure of being a teenager in the harsh media spotlight took its toll on the young star. After a long break, she's finally making a comeback. It's about time audiences revisit the roles that made her famous, and some that... didn't.
20. InAPPropriate Comedy (2013)
Releasing three movies in a year would be a challenge for any actor, but sadly all three of Lohan's 2013 projects were duds. InAPPropriate Comedy starring Adrian Brody being the worst of the bunch.
Masterminded by none other than the 'ShamWow' guy Vince Offer, this movie rightly has a 0% approval rating on Rotten Tomatoes. Deliberately as offensive as possible and lacking in any form of point, it's a wonder how SquareOne Entertainment (the same production company that brought us The Imitation Game) thought this was a good idea. ShamWow money not well spent, Offer.
19. Among the Shadows (2019)
Shot in late 2015, there's a reason this film took so long to hit the international market. The genre 'werewolf detective thriller' isn't a very popular one. When they threw bad acting and a cheesy script into the mix, this film was destined for failure.
If only Among the Shadows didn't take itself so seriously, it could have garnered a cult appreciation. This definitely isn't the indie gem Lohan was hoping for when she signed up for the project. Technically, this film can be lumped with her ill-fated mid-2010s comeback attempt, and promptly forgotten.
18. The Canyons (2013)
Billed as a flashy thriller set in young Hollywood, Lohan is Tara, an actress having an affair with her co-star under the watchful eye of the angry 'trust fund baby' director. She won the worst actress Razzie for this one, but there was a lot going on behind closed doors.
The lack of sympathetic characters is one thing, but Tara is yet another powerless and manipulative female in a trope that's been done to death and is problematic at best. Troublingly, it was later reported Lohan was struggling with addiction during filming and was extremely uncomfortable filming the sex scene.
17. Scary Movie 5 (2013)
By this point, the Scary Movie franchise was well and truly past its sell-by date, but Lohan's cameo opposite Charlie Sheen was heavily billed at the time, so fans tuned in. The bizarre sex-oriented scene tried way too hard and came across as more uncomfortable than anything else.
Lohan had it written into her contract that she wasn't to kiss Sheen, so body doubles were used. According to Sheen the two grew close during filming, but given all we know about the pair this probably wasn't a good thing. With an average rating of 2.2/10 on Rotten Tomatoes, the consensus calls the movie "Juvenile even by Scary Movie standards".
16. Liz & Dick (2012)
Chronicling the relationship between Elizabeth Taylor and Richard Burton, Liz & Dick saw Lohan playing one of her idols. The Lifetime movie premiered to 3.5 million viewers, a lower number than expected given the heavy marketing strategy.
Lohan's performance was critically torn to shreds, with every tabloid jumping at the opportunity to poke fun at the troubled star. It's telling of the times that so much negativity was directed at the 26-year-old. It's rare these days that any tabloid will lay sole blame on a lead actor for a poor film, especially when it was made-for-TV.
15. I know Who Killed Me (2007)
Lindsay's first foray into thriller was heavily publicized in 2007. It was her first 'adult' role and after a couple of years' break fans were eager to see where she would go next. I Know Who Killed Me did not meet those high expectations and swept the 2008 Razzie awards.
I Know Who Killed Me has since gained cult status for its bold stylization and surreal nature, earning the title of 'midnight movie' alongside quirky classics like The Rocky Horror Picture Show and Showgirls. While Lohan's first film since her Disney days may not have been the critical success she hoped for, it has certainly left a mark in pop culture lore.
14. Labor Pains (2009)
Returning to her rom-com routes, Lohan's Labor Pains is a campy comedy about a young woman who pretends to be pregnant to avoid losing her job and the 9 months of drama that follow.
While not particularly memorable, Labor Pains is a harmless and silly TV movie. While it could be seen that the film glorifies a treatment of pregnant women that is wholly inaccurate, the film does well to balance the reality of pain and emotion that comes with growing a human. Your employers should be empathetic, pregnant or not, is a good message after all. There are some genuinely funny moments as Lohan reminds audiences of her comedic prowess.
13. Get a Clue (2002)
Considering the success of Agent Cody Banks and Spy Kids you can see why Get a Clue is actually a pioneer of the teen-spy genre. Mini socialite and gossip columnist Lexy tries to solve the mystery of her teachers' disappearance.
The third of Lohan's three-movie-deal with Disney (after The Parent Trap and Life-Size) is like Gossip Girl meets Nancy Drew. Remember this is a Disney movie, so the performances aren't exactly Oscar-worthy, but if you're looking for a cute movie for tweens to enjoy with a strong female lead Get a Clue will do the trick. Also, the fashion is very on-trend.
12. Just My Luck (2006)
A high-flying New Yorker known as the 'luckiest woman around' has a chance meeting with a down-and-out music manager (Chris Pine) at a masquerade party. When they kiss, their luck swaps, and chaos ensues.
The rumors of Lohan's partying and bad behavior on set overshadowed the promotion of this light-hearted comedy. Pine compared working with her to being around The Beatles, referring to the crowds of press and fans that followed her everywhere she went. Young Pine is fun, and the movie was a launchpad for British pop group McFly to make it make in the States. According to Lohan's father, it was during the filming of Just My Luck that she overdosed on cocaine for the first time.
11. Herbie Fully Loaded (2005)
This is one of those films your dad will want to watch with you. Based on the classic Herbie franchise that began in 1968, Lohan plays aspiring NASCAR competitor Maggie, the latest to acquire the Bug with a mind of its own.
This movie was a certified box office hit, and with the mix of generational nostalgia, it's not hard to see why. Herbie Fully Loaded is fun and fast, and Lohan is great next to Michael Keaton, who plays her father, and Matt Dillon, her competitor. If your kid likes cars, they'll love this movie.
10. A Prairie Home Companion (2006)
Her role may be small, but Lohan appeared among some heavy hitters in Robert Altman's final film. Set on the final night of a fictional radio show, a lively bunch of musical characters sing their final farewells as they come to terms with the ending.
The film is quirky and clever and a must-see for any country and western fan. Woody Harrelson, John C Reilly, and Meryl Streep are brilliant, as always, and Lohan really does hold her own. It's a shame knowing how hard things were getting for her at this time, and that working with icons in the industry couldn't save her.
9. Chapter 27 (2009)
This film stars Jared Leto as Mark David Chapman, the man who murdered John Lennon. Inspired by the book Let Me Take You Down by Jack Jones, Chapter 27 depicts Chapman's life in the lead up to his crime. Lohan plays Chapman's sympathetic friend Jude.
Critically, the film, aside from Leto's heralded performance, was not well received. Sean Lennon, the son of John Lennon, referred to Lohan's involvement as 'tacky', and Yoko Ono refused to watch or speak of the film. The film is more crime-thriller than it is biographical documentation of what happened, and it's this angle that seems to have angered audiences most. Either way, Lohan is solid as Jude and a breath of fresh air next to Leto's Chapman. The family's critiques were more aimed at Lohan's reputation than her acting ability, which is interesting considering Sean Lennon referred to himself as a friend of hers.
8. Life-Size (2000)
Supermodel Tyra Banks' first foray into the acting world was starring in the Disney Channel movie Life-Size. Lohan plays 11-year-old Casey who has recently lost her mother. When she finds a book of spells, she decides to try to bring her mother back to life. Sadly her plan fails, and instead she brings to life her fashion doll Eve.
Young Lohan's acting is top-notch in this sweet, magical tale about a young girl and her father coming together in tragedy. Banks is particularly memorable, and a perfect casting choice for 'human Barbie' Eve. This movie was a worthy gem in any young girls' DVD collection and still holds up today.
7. Confessions of a Teenage Drama Queen (2004)
In a movie that plays out like a Wattpad fan fiction, a self-centered New York City teen who dubbed herself 'Lola' moves to a small town and struggles to shine. Bonding with the equally unpopular Ella over their love of a band named Sidarthur, the girls decide to travel to New York to catch their last ever concert.
Based on the novel of the same name by Dyan Sheldon, this movie is the epitome of over the top, and it owns it. From the bold colors and costuming to the showstopping musical number 'Drama Queen (That Girl)' recorded and performed by Lohan, it lets girls be loud and proud. At a time when print media thrived on negativity, young girls needed this positivity. The confidence in Lohan's performance is another example of why she became an icon.
6. Machete (2010)
Mexploitation mega-hit Machete stars Danny Trejo as an ex-Federale on the hunt for revenge. Like most movies of this genre, there's violence, gore, and nudity galore, mixed with hilarious one-liners and a truly bizarre cast of characters.
No spoilers here but the movie is R-rated for a reason, and Lohan's character arc is no doubt a large part of that. While the film is very different for her and has its place on every Robert Rodriguez fans' shelf, it is very different from the rest of Lohan's movies. Proceed with caution!
5. Bobby (2006)
Written and directed by Emilio Estévez, Bobby is a rare biopic that, while based on true events, tells the story of the effect those events had on ordinary people and does them justice. Estévez stated he felt fated to create this film, having been deeply affected by the assassination of Robert F Kennedy as a child.
Estévez wrote Lohan's character Diane Howser after speaking with a hotel receptionist. She told him she had been a volunteer for JFK, and how she had married a young man to keep him out of Vietnam. Lohan's performance is strong and sincere, and fans had high hopes that she would continue on this trajectory. Knowing this is the level she's capable of, we're looking forward to her upcoming projects.
4. Georgia Rule (2007)
This movie is a powerful one about flawed women and the importance of honesty and family. Despite a strong cast that includes Jane Fonda, Felicity Huffman, and Dermot Mulroney, Georgia Rule's release was completely overshadowed by the gossip column tales of Lohan's on-set behavior.
James G Robson (the CEO of Morgan Creek Productions) wrote a letter that was subsequently released to the press, describing Lohan's behavior as "discourteous, irresponsible and unprofessional". Despite this, her performance in the final product is moving. Having experienced similar familial struggles to her character, it's understandable that this role would have hit home.
3. The Parent Trap (1998)
Who could forget the movie that started it all? In The Parent Trap little Lindsay showed talent far beyond her years by playing both twins in this family classic. A remake of the 1961 Disney original, the film sees twin girls separated at birth miraculously reunited at a summer camp. They decide to swap places in a bid to reunite their separated parents.
For years after the movie's release, Lohan had to assure people she wasn't actually a twin. Her chemistry with herself is just that believable. Beating out Scarlett Johansson, Mara Wilson, Michelle Trachtenberg, and Jena Malone was no small feat, but it's not hard to see why the charismatic redhead was the perfect choice for the role. The Parent Trap remains one of the best family movies of the 1990s, with lines and laughs for the kids and the grownups.
2. Mean Girls (2004)
Almost taking the top spot is Tina Fey's cultural phenomenon Mean Girls. The movie tells the story of Cady, a recent immigrant from Africa who finds herself entangled with the cruel popular girls at her school. In a bid to take them down, she slowly becomes the thing she swore to destroy.
There are countless articles about why Mean Girls is as important and memorable as it is, but to focus on Lohan's performance, she's just so believable. Being a teenager is a nightmare, and Mean Girls perfectly captures how devastating high school can feel, but how ultimately unimportant popularity is. While Lohan may have originally wanted to play Regina, she embodies an outsider so well, and that's why audiences relate to her so much.
1. Freaky Friday (2003)
Freaky Friday could easily have been another body swap remake forgotten in time, but with their fingers surprisingly on the pulse, Disney created a time capsule of 2003 that appealed to audiences far and wide. Jamie Lee Curtis plays a hardworking psychiatrist with time and empathy for everyone but her sullen daughter, and Lindsay Lohan is a misunderstood teen desperate to express herself and be seen by not only the school hottie (Chad Michael Murray) but her mom.
The soundtrack, the fashion, the writing, the direction; there's nothing not to love about this film. Curtis and Lohan are brilliant together, and hilariously believable acting as each other's characters. While Mean Girls was the film that cemented Lindsay Lohan as the 'It Girl', it was Freaky Friday that made her a household name. With the ultimate show of girl power, she inspired everyone old enough to hold a guitar to start a band. There's a reason her first album 'Speak' went platinum. We can't wait to see what she does next.