Accept Lindsay Lohan as the leading actress of our day, or go. Quickly. Lindsay played every type of character in her early years, including the attractive British overnight camper, dramatic theater kid, tomboy, Material Girl, and Homeschooled Jungle FreakTM, to mention just a few.
Lindsay had become a real household name by the time she was 12 years old because of the dramatic chokehold she put us all in. But throughout the late 2000s, her name was mentioned for various reasons—most frequently in headlines rather than on cinema screens.
So, what has our gal been doing since that, you ask? The reality series Lindsay Lohan’s Beach Club, which focuses on her VIP vacation ownership of Mykonos Beach House, premiered on MTV in 2019.
But it didn’t end there—Lindsay announced in 2019 that she was restarting her acting career during a segment on CNN’s New Year’s Eve special! Rejoice! And it gets better: In March 2021, Lindsay agreed to a multi-picture agreement with Netflix, offering a number of fresh movies, including the upcoming holiday film Falling for Christmas.
Fans are ecstatic to see Lohan in another classic romantic comedy, this one set in a nice Christmas setting that fits the mood of the last comfortable days of 2022. Only time will tell, though, if it lives up to the standards set by her past highly-rated movies on Letterbox. For her fans, here are 21 movies that you should consider watching.
21. Falling For Christmas (2022)
Falling for Christmas is a 2022 American holiday romance comedy film directed by Janeen Damian. In the movie, Lohan portrays a privileged heiress who loses her memory after colliding with a ski slope and ends up in the care of a widowed lodge owner (Overstreet) for the holidays.
Following a string of professional setbacks, while undergoing addiction treatment and resolving legal troubles, it was Lohan’s first role in a major production in more than ten years. The movie’s producers are Brad Krevoy and Michael Damian. It was initially revealed in May 2021.
Fans were excited to see Lindsay Lohan return to her classic rom-com roots, but for better or worse, the film will not really go beyond a formulaic holiday story. The movie avoids taking any of the genre’s risks while delivering a welcome Christmas energy and effective use of the forced proximity trope.
Falling for Christmas is a pleasant movie that will help viewers get into the Christmas spirit, even though it isn’t necessarily a thought-provoking seasonal masterpiece. Even though Sierra is one of her least likable roles, Lohan’s infectious energy is apparent in every scene, a hint that the crowd’s favorite actress still gets it and is eager for more.
20. InAPPropriate Comedy (2013)
Any actor would find it difficult to have three films come out in a calendar year, but Lohan’s 2013 offerings were all failures. The poorest of the bunch is Adrian Brody in an inappropriate comedy.
This film, created by no other than the “Sham Wow” guy Vince Offer, has a 100% disapproval rating on Rotten Tomatoes. It’s amazing that Square One Entertainment, the same production firm that gave us The Imitation Game, thought this was a decent idea given that it’s purposefully as possible offensive and without any message. Sham, Wow, poor use of money, offer.
19. Among the Shadows (2019)
In 2019, Tiago Mesquita and Mark Morgan released the supernatural horror thriller movie Among the Shadows in the United States. In addition to Lindsay Lohan and Gianni Capaldi, who play minor characters, the movie also stars Charlotte Beckett, Dominik Madani, Reynald Bialès, Barry Jay Minoff, Kristoffel Verdonck, Olivier Englebert, Peter Organ, Jean-Michel Vovk, and Lindsay Verdonck.
The story follows a private eye which is descended from a family of werewolves as she investigates her uncle’s slaying and unearths a political plan. On March 5, 2019, the movie went on demand via video.
There’s a reason this movie took so long to reach the worldwide market; it was shot in late 2015. Werewolf detective thriller is not a very well-liked genre. This movie was destined to fail when they combined lousy acting with a corny storyline.
The game Among the Shadows might have developed a cult following if it hadn’t taken itself so seriously. Lohan wasn’t expecting this to be an independent masterpiece when she agreed to work on the film. Technically, this movie can be dismissed along with her disastrous mid-2010s comeback effort.
Werewolves that are acting on the orders of an unidentified person attack joggers at random, spreading fear throughout Brussels. Harry Goldstone, a werewolf who works on President Richard Sherman’s reelection campaign for the European Federation, is shot and killed by werewolf Randall Jackson as part of the same scheme.
Harry’s strategy manual for Richard’s impending discussion with John Kilborn’s opponent is stolen by Randall. Harry phones his werewolf niece, private eye Kristy Wolfe, just before he dies, telling her that Randall assaulted him.
18. The Canyons (2013)
Lohan plays Tara, an actor who has an affair with her co-star while being observed by the enraged “trust fund baby” director in this dazzling thriller set in early Hollywood. Although there was a lot happening behind closed doors, she earned the Razzie for worst actress for this role.
The absence of likable people is one thing, but Tara is just another weak, cunning female in a genre that has been overused and is, at best problematic. Unsettling, it was later revealed that Lohan was suffering from addiction while the sequence was being filmed and that she felt very awkward.
17. Scary Movie 5 (2013)
Scary Movie V premiered on April 12, 2013, and Dimension Films handled distribution. The movie has taken in roughly $32 million nationally and about $78.6 million internationally.
After bringing their newborn child home from the hospital, the husband, portrayed by Simon Rex, and wife, portrayed by American actress and singer Ashley Tisdale, go through several strange occurrences. The family has spoken with paranormal experts after realizing that a demon is stalking them.
Fans tuned in despite the fact that the Scary Movie franchise had long since passed its prime, but Lohan’s debut alongside Charlie Sheen was much anticipated at the time. The odd sex-focused scene was attempted way too hard and came off as more uneasy than anything else.
Body doubles were employed because Lohan had it in her agreement that she wasn’t supposed to kiss Sheen. Given everything we know about the two, it’s probably not a good thing that Sheen claims they became close during filming. The consensus describes the film as “Juvenile even by Scary Movie standards,” with a Rotten Tomatoes average rating of 2.2/10.
16. Liz and Dick (2012)
Liz & Dick, which followed the romance of Elizabeth Taylor and Richard Burton, included Lohan as a role model. 3.5 million people watched the Lifetime movie’s premiere, which was fewer than anticipated, given the aggressive marketing campaign.
Every tabloid jumped at the chance to make fun of the troubled star as they ripped at Lohan’s performance in the press. The fact that the 26-year-old received so much hate speaks volumes about the times. Nowadays, it’s uncommon for a tabloid to single out a star actor for blame when a movie is subpar, especially if it was created for television.
15. I know Who Killed Me (2007)
TriStar Pictures’ July 27, 2007, release of I Know Who Killed Me was a box office and critical flop, and it has since been dubbed one of the worst movies ever filmed.
It did, however, have a more lucrative home video performance, with anticipated domestic DVD sales nearly quadrupling its U.S. box office gross. After that, the movie gained a cult following, and vintage cinemas and film festivals organized a number of showing of it.
A serial killer who kidnaps and torments young women, keeping them hostage for weeks before killing them, is terrorizing the sleepy suburb of New Salem. A pianist and aspiring writer named Aubrey Fleming vanishes while out with her friends, making her appear to be his most recent victim.
Later, she is seen on an examination table with her hands in contact with dry ice, shackled, and gagged. The special FBI Task Force assembled to find the murderer starts to lose faith in its ability to catch him before it’s too late.
In 2007, Lindsay’s debut thriller received a lot of media attention. After a pause of a few years, people were excited to find out where she would have to go next because it was her first “adult” job. Despite having great hopes, I Know Who Killed Me swept the 2008 Razzie awards.
I Know Who Killed Me, along with other oddball masterpieces like The Rocky Horror Picture Show and Showgirls, has now attained cult status for its daring utilization and surrealistic nature. While Lohan’s first movie after her time at Disney may not have received the kind of reviews she had hoped for, it has undoubtedly impacted pop culture.
14. Labor Pains (2009)
Lara Shapiro and Stacy Kramer’s 2009 romantic comedy Labor Pains is an American production. Luke Kirby, Bridgit Mendler, Chris Parnell, Cheryl Hines, and Kevin Covais are some of the actors who appear in it. On June 19, 2009, the movie was exclusively shown in theatres in Europe, Latin America, and the United Arab Emirates.
The movie debuted on ABC Family on July 19, 2009, in the United States. According to the network, it was the week’s #1 cable film among key female demographic categories. It attracted 2 million views, a good prime-time audience for ABC Family. On August 4 and August 31 in the United States and the United Kingdom, respectively, Labor Pains was made available on DVD and Blu-ray.
Returning to her romantic comedy roots, Lohan’s Labor Pains is a zany comedy about a young lady who fakes being pregnant in order to keep her work and the subsequent nine months of drama. Labor Pains is a funny TV movie that isn’t particularly noteworthy but is nonetheless enjoyable.
The movie does a good job of balancing the realities of pain and emotion that come with growing a human, even though it might be argued that it promotes a behavior of pregnant women that is entirely wrong. Regardless of whether you are pregnant, your employers should be sympathetic. There are several very amusing parts where Lohan shows off her comedy skills.
13. Get A Clue (2002)
You can see why, Get a Clue is truly considered a pioneer of the teen-spy genre, given the popularity of Agent Cody Banks and Spy Kids. Lexy, a young socialite, and gossip blogger, want to discover what happened to her teachers.
After The Parental Trap and Life-Size, the third film in Lohan’s three-movie contract with Disney is comparable to Gossip Girl and Nancy Drew. Get a Clue will do the trick if you’re looking for a pleasant movie for adolescents to enjoy with a strong female lead. Keep in mind that this is a Disney film, so the performances aren’t quite Oscar-worthy. The clothing is also quite current.
12. Just My Luck (2006)
At a masquerade party, a successful New Yorker known as the “luckiest woman around” meets by chance a struggling music manager (Chris Pine). When they kiss, their good fortunes switch, and mayhem results.
The publicity for this lighthearted comedy was marred by accusations of Lohan’s drinking and inappropriate behavior during production. In reference to the throngs of reporters and admirers who trailed her around, Pine equated working with her to being in the presence of The Beatles.
Young Pine is entertaining, and the film served as a springboard for the American success of the British pop group McFly. Her first cocaine overdose, according to Lohan’s father, occurred while she was filming Just My Luck.
11. Herbie Fully Loaded (2005)
One of those movies that your father will want to see with you is this one. Lohan portrays Maggie, the most recent owner of the Bug with a mind of its own, in this 1968 remake of the iconic Herbie franchise.
It’s not hard to understand why this movie was a box office success, given the mixture of generational nostalgia. Herbie Fully Loaded is a fast-paced, enjoyable movie, and Lohan works well with Matt Dillon, who portrays her rival, and Michael Keaton, who plays her father. Your child will adore this movie if they enjoy vehicles.
10. A Prairie Home Companion (2006)
Despite having a little part, Lohan shared the screen with some notable actors in Robert Altman’s final movie. A colorful cast of musical performers sings their final goodbyes as they come to grips with the ending in this imaginary radio show’s final episode.
Any fan of country and western movies must watch this funny, intelligent movie. Lohan truly does hold her own, and Woody Harrelson, John C. Reilly, and Meryl Streep are all excellent, as usual. Knowing how difficult things were for her at this point and how working with industry legends couldn’t save her is regrettable.
9. Chapter 27 (2009)
In this movie, Jared Leto plays Mark David Chapman, the assassin of John Lennon. Chapman’s life prior to his crime is portrayed in Chapter 27, which was inspired by Jack Jones’ novel Let Me Take You Down. Lohan portrays Jude, a compassionate buddy of Chapman.
Aside from Leto’s lauded performance, the movie did not garner favorable reviews. Sean Lennon, John Lennon’s son, described Lindsay Lohan’s involvement as “tacky,” while Yoko Ono declined to see or discuss the movie.
This aspect of the movie, which focuses more on a crime thriller than a biographical account of what happened, seems to have infuriated viewers the most. In any case, Leto’s Chapman is a fresh breath of air next to Lohan’s Jude. It’s interesting that the family criticized Lohan more for her reputation than for her acting skills, given that Sean Lennon described himself as a friend of hers.
8. Life Size (2000)
Tyra Banks, a supermodel, made her acting debut as the lead in the Life-Size movie on the Disney Channel. Casey, an 11-year-old who recently lost her mother, is portrayed by Lohan. She resolves to try to resurrect her mother after discovering a book of magic. Sadly, her scheme backfires, and she instead summons Eve, her fashion doll, to life.
In this charming, enchanting tale of a young girl and her dad coming together in sorrow, Young Lohan plays the lead role with superb acting. Banks is a standout performer and the ideal Eve, the “human Barbie,” casting decision. Any young girl’s DVD collection would benefit from having this film, which is still relevant today.
7. Confessions of a Teenage Drama Queen (2004)
A self-centered New York City teen named “Lola” relocates to a rural village and fights to stand out in a film that reads like a Wattpad fan fiction. Together with the similarly unpopular Ella, the girls decide to go to New York to see Sidarthur’s final show after becoming friends through their shared love of the band.
This movie, which is about the height of excess and embraces it, is based on Dyan Sheldon’s novel of the same name. It allows girls to be loud and proud, from the vivid colors and costumes to the unforgettable musical number ‘Drama Queen (That Girl),’ which Lohan recorded and sang.
Young ladies required this positivity at a period when traditional media thrived on negativity. Another illustration of why Lohan became an icon is an assurance in her performance.
6. Machete (2010)
In the massively successful mutilation film Machete, Danny Trejo plays an ex-Federale out for vengeance. The usual violence, gore, and naughtiness are all present, along with some humorous one-liners and a very odd group of characters.
Without giving anything away, the film is R-rated for a reason, and Lohan’s character journey undoubtedly plays a significant role in that. It is incredibly distinct from the rest of Lohan’s movies, even though the movie is very different for her and belongs on any Robert Rodriguez fan’s shelf. Be careful as you go.
5. Bobby (2006)
Bobby is a unique biopic that, despite being based on real events, tells the tale of how those events affected regular people and does them justice. It was directed and written by Emilio Estévez. Given that he was profoundly impacted by the killing of Robert F. Kennedy when he was a child, Estévez claimed he felt destined to make this movie.
Following a conversation with a hotel front desk clerk, Estévez created Lohan’s character Diane Howser. She revealed to him that she had volunteered for JFK and had married a young man in order to keep him out of Vietnam.
Lohan’s performance is powerful and passionate, and her supporters had high expectations for her future. We’re excited to see what she has in store for us in the future, knowing that this is the level she is capable of.
4. Georgia Rule (2007)
This moving film explores the value of honesty and family while focusing on the flaws of flawed women. The gossip column stories about Lohan’s antics on the set entirely overshadowed the release of Georgia Rule, despite having a solid ensemble that features Jane Fonda, Felicity Huffman, and Dermot Mulroney.
In a letter that was later made public, Morgan Creek Productions CEO James G. Robson called Lindsay Lohan’s actions “discourteous, irresponsible, and disrespectful.” Despite this, the ultimate performance she gives is powerful.
It makes sense that this play would have struck close to home for her because she has gone through comparable familial issues as her character.
3. The Parent Trap (1998)
Who could ever forget the film that began it all? Little Lindsay performed the roles of both twins in the family classic The Parent Trap, displaying brilliance much beyond her years.
In this retelling of the 1961 Disney classic, twin twins who were separated at birth are mysteriously brought together at a summer camp. To get their estranged parents back together, they decide to switch places.
After the film’s debut, Lohan had to repeatedly reassure people that she wasn’t a twin. She has a believable chemistry with herself. It was no easy task to win the role over Scarlett Johansson, Mara Wilson, Michelle Trachtenberg, and Jena Malone, but it’s clear why the charming redhead was the ideal candidate. One of the top family films of the 1990s, The Parent Trap still has jokes and laughter for both kids and adults.
2. Mean Girls (2004)
American teen comedy Mean Girls was released in 2004 and were written and directed by Mark Waters. Lindsay Lohan, Rachel McAdams, Lacey Chabert, Amanda Seyfried, Tim Meadows, Ana Gasteyer, Amy Poehler, and Fey are among the actors who appear in the movie.
The 2002 book Queen Bees and Wannabes by Rosalind Wiseman, which discusses female high school social cliques, bullying at school, and the negative impact these behaviors can have on children, is a major inspiration for this story.
Fey also used her own Upper Darby High School experience as inspiration for several of the movie’s themes. The story revolves around a naive teenage girl who must negotiate the social order of a contemporary American high school after years of being homeschooled by her parents while they were undertaking research in Africa.
Mean Girls, the cultural sensation created by Tina Fey, is almost in the first place. The film follows Cady, a recent African immigrant who becomes involved with the very famous girls at her school. She gradually transforms into the creature she vowed to eliminate in an effort to defeat them.
There are numerous essays explaining why Mean Girls is so significant and memorable, but to concentrate on Lohan’s portrayal, she seems so real. Teenagers’ worst dread is well captured in Mean Girls, which also shows how superficial popularity is and how painful high school can feel. Although Lohan may have first intended to play Regina, her ability to portray an outsider makes her so relatable to viewers.
1. Freaky Friday (2003)
Freaky Friday could have easily been another body swap remake lost in history, but Disney managed to produce a time capsule of 2003 that was well received by viewers all over the world. Lindsay Lohan is a misunderstood youngster trying to express herself and be seen by not just the school hottie (Chad Michael Murray) but also her mother. Jamie Lee Curtis plays a busy psychiatrist with time and compassion for everyone who saves her grumpy daughter.
There is nothing not to adore about this movie, not the soundtrack, not the clothes, not the screenplay, not the direction. Together, Curtis and Lohan are brilliant, and their portrayals of one other’s personas are hilariously convincing. Lindsay Lohan became known to the general public because of Freaky Friday, not Mean Girls, which established her as the “It Girl.”
She gave the ultimate demonstration of lady power and encouraged everyone who could wield a guitar to form a band. Her debut record, “Speak,” achieved platinum status for a reason. We eagerly anticipate her future actions.