After the birth of her first child with spouse Bader Shammas, actress Lindsay Lohan has begun a peaceful new chapter in her life, reveling in the delights of motherhood. Celebrities and fans who have supported Lohan throughout her career and appreciate her more sedate lifestyle have expressed their joy at the birth of her firstborn. The actress rose to prominence as a child model and actress, making her film debut at 11 in Disney’s 1998 version of The Parent Trap.
But her personal problems and legal concerns often overshadowed her successful career. After 2010, her film roles drastically decreased due to her struggles with substance abuse and subsequent legal difficulties. Still, Lohan showed her strength by slowly returning to the entertainment industry with television projects, including the OWN docuseries Lindsay (2014) and the Netflix film Sick Note (2018). She also dabbled in business by creating a Mykonos beach club, the subject of the 2019 MTV reality series Lindsay Lohan’s Beach Club.
Lohan’s journey, filled with incredible success and public turbulence, highlights her enduring talent and resilience in the face of adversity, establishing her as one of the most recognizable figures in pop culture. So, to celebrate her new role as a mother, let’s look back at her acting career, spotlighting some of her most memorable parts yet.
10. Labor Pains (2009)
Lindsay Lohan stars as Thea Clayhill in the romantic comedy Labor Pains. The movie centers around Thea’s life, who, fearing she’s about to lose her job, fakes a pregnancy to avoid getting fired. Luke Kirby plays Nick Steinwald, Thea’s boss and love interest, and Cheryl Hines plays Thea’s domineering elder sister, Lisa, in this film directed by Lara Shapiro. Kevin Covais and Aaron Yoo both make appearances as Thea’s supportive coworkers and friends.
Thea’s lie leads to increasingly absurd and comical scenarios, such as her wearing artificial baby bumps and pretending to have pregnancy symptoms. As time goes on, she receives several compliments and even a promotion as a result of her lie. As she goes through the motions of her fake pregnancy, she begins to feel romantic feelings for her boss, Nick.
9. Herbie: Fully Loaded (2005)
Angela Robinson and Robert Simonds’ Herbie: Fully Loaded is a sports comedy film released by Walt Disney Pictures. The film is the fifth and final installment in the Herbie film series, which follows the exploits of a talking 1963 Volkswagen Beetle. The main character, Maggie Peyton, played by Lindsay Lohan, is a third-generation member of a NASCAR family and hopes to win the series championship one day. Still, her overprotective father, Ray Peyton Sr. (played by Michael Keaton), wants her to find another path in life.
Maggie receives a beat-up old Volkswagen Beetle as her graduation present, setting off the story’s events. It doesn’t take long for her to realize this isn’t just any car. Herbie, as the automobile is known, is intelligent and quirky, with a natural talent for speed. When Maggie decides to fix Herbie up, she learns about his exceptional skills. Maggie, aided by Herbie, enters local racing competitions and catches the eye of Trip Murphy (Matt Dillon), a champion race car driver. In a fit of paranoia, Trip dares Herbie to one last race. This sets off a hilarious and action-packed chain of events where Maggie and Herbie compete in high-stakes races and pull off daring acts to show their value.
8. Georgia Rule (2007)
Garry Marshall’s Georgia Rule is a comedy-drama that stars Jane Fonda, Lindsay Lohan, and Felicity Huffman. The intergenerational narrative of this film delves deeply into the complex dynamics of the female bond within a family. Lindsay Lohan plays Rachel, a rebellious and troubled San Francisco teen. After Rachel’s recent wild activities, her distraught mother, Lilly (Felicity Huffman), sends her to her strict grandmother Georgia (Jane Fonda), in the small town of Hull, Idaho, for the summer.
Former educator Georgia enforces a stringent set of moral guidelines, known as the “Georgia Rule,” on her family. This shift initiates a summer of transformation for all three ladies. Rachel has difficulty adapting to her grandmother’s strict affection and discipline because she is used to living an untamed and carefree lifestyle. However, Lilly has her own problems to deal with, such as her tense relationship with her daughter and her murky history.
7. Just My Luck (2006)
Directed by Donald Petrie, Just My Luck stars Lindsay Lohan as Ashley Albright, a young professional in New York City who seems perpetually gifted with excellent luck. Ashley has all the good fortune in the world. She is an associate at a well-known public relations agency and is successful in every aspect of her life. Everything changes, however, when she kisses a stranger, Jake Hardin (Chris Pine), at a masquerade party.
Ashley is unaware that Jake is the unluckiest guy in New York, and their kiss leads to their exchanging fortunes. While Jake’s luck seems to be turning around, Ashley’s seemingly perfect existence collapses around her. As she tries to cope with her recent setback, she also comes to terms with her feelings for Jake. The rest of the film follows Ashley as she tries to escape this strange circumstance and regain her good fortune without giving up her chance at true love.
6. Bobby (2006)
Bobby revisits the hours leading up to U.S. Senator Robert F. Kennedy’s assassination in the Ambassador Hotel in Los Angeles on June 4, 1968, following his victory in the California Democratic primary. The film uses a fictional narrative to depict real-life events, following the lives of 22 people staying at the hotel on that fatal day. The film’s ensemble cast features Lindsay Lohan, Anthony Hopkins, Helen Hunt, Elijah Wood, Laurence Fishburne, and Sharon Stone, among others.
Diane, played by Lindsay Lohan, is a young woman who marries her best friend William (Elijah Wood) to help him avoid being conscripted during the Vietnam War. Her portrayal is a remark on the generational divide caused by the Vietnam War and the activism and enthusiasm that characterized many young people at the time. Introspective and heartbreaking, Bobby looks at a pivotal period in American history and the impact of John F. Kennedy’s assassination on various people. The film received mixed reviews from critics, but it was commended for its ambitious storytelling and performances by its ensemble.
5. Confessions of a Teenage Drama Queen (2004)
Based on Dyan Sheldon’s 1999 novel, Confessions of a Teenage Drama Queen is a teen musical comedy film directed by Sara Sugarman. Lindsay Lohan plays Mary Elizabeth “Lola” Steppe, a flamboyant teenager passionate about theatre and dreams of becoming a famous actress. Lola’s life is turned upside down in the film due to her family’s relocation from the exciting Big Apple to the tranquil suburb of Dellwood, New Jersey. Lola sees this as a tragic setback that will prevent her from ever achieving her goal of being a famous actress.
In her new school, Lola butts heads with the popular girl Carla Santini, played by Megan Fox, who is also a big fan of the rock band Sidarthur. The rivalry between Lola and Carla is central to the plot. A sequence of mishaps and a fantastic encounter with the band’s lead singer ensue after Lola and her new friend Ella (Alison Pill) secure tickets to their favorite band’s farewell show and after-party. Confessions of a Teenage Drama Queen did well at the box office and is now considered a cult classic despite receiving mixed reviews from reviewers.
4. A Prairie Home Companion (2006)
Robert Altman’s A Prairie Home Companion is a comedy film featuring a large cast inspired by Garrison Keillor’s eponymous radio variety show. The film provides a dramatized narrative of what happened during the production and features Meryl Streep, Lily Tomlin, Kevin Kline, Woody Harrelson, John C. Reilly, Tommy Lee Jones, and Lindsay Lohan. The story interweaves the cast’s personal tales with the show’s on-air performances, creating a multi-layered narrative filled with humor, music, and nostalgia.
Lindsay Lohan plays Lola Johnson, the angst-filled daughter of Yolanda Johnson (Meryl Streep), one of the show’s singing duet sisters. Lohan’s character is a young poet going through a rebellious phase. Lola brings a youthful dimension to the cast and counterbalances the show’s traditional, folksy charm. A Prairie Home Companion gave Lohan a unique opportunity to showcase her acting skills with some of Hollywood’s most respected stars. Her performance of Lola is emotional and sincere, and she holds her own alongside actresses like Streep and Tomlin.
3. Freaky Friday (2003)
Freaky Friday is a fantasy comedic remake of the 1976 film, adapted from Mary Rodgers’ novel. The plot centers around a mother and daughter who switch bodies and are compelled to live each other’s life for a day thanks to a supernatural fortune cookie. Jamie Lee Curtis plays Tess Coleman, the workaholic psychiatrist mother, and Lindsay Lohan stars as her rebellious teenage daughter, Anna. Due to their inability to see things from each other’s point of view, these two protagonists are continuously at odds with one another.
The body-swapping makes them experience life as the other person does, allowing them to better comprehend and empathize with one another’s challenges. Lindsay Lohan shines as the troubled teen and the mature, somewhat frantic mother who finds herself in the body of a teenager. Her chemistry with Jamie Lee Curtis is one of the film’s most essential elements. The comedy, charisma, and performances of the film’s two leading ladies earned Freaky Friday widespread acclaim and made it a financial and critical triumph. The film also received several award nominations, with Curtis winning a Golden Globe for her performance.
2. The Parent Trap (1998)
Written and directed by Nancy Meyers, The Parent Trap is a romantic comedy-drama released in 1998. It is an adaptation of Erich Kästner’s 1949 German novel Lottie and Lisa (Das doppelte Lottchen), and it is a remake of the 1961 film of the same name. Lindsay Lohan starred as Hallie Parker and Annie James, identical twin sisters who separated shortly after birth after their parents, Elizabeth (Natasha Richardson) and Nick (Dennis Quaid), divorced. The girls grow up unconscious of each other’s presence – Hallie lives with Nick in Napa Valley, California, and Annie lives with Elizabeth in London.
The story kicks up when the twins meet each other by chance at a summer camp. After some early animosity, they come to terms with their shared siblinghood and hatch a plot to trade places to get their divorced parents back together. The story unfolding is a touching and ingenious look at the love between sisters, the importance of family, and the extent to which the twins will reunite with their parents. Over $92 million was made from The Parent Trap worldwide, making it a critical and commercial success. With this film, Lohan launched her career and eventually became one of the most famous child actors of all time.
1. Mean Girls (2004)
Mark Waters and Tina Fey’s Mean Girls is a teen comedy film that takes a satirical look at high school life, focusing on social cliques and the harmful consequences they may have on teens. Mainly based on Rosalind Wiseman’s non-fiction book Queen Bees and Wannabes, published in 2002, the film follows Cady Heron, played by Lindsay Lohan, a 16-year-old who has spent the majority of her life in Africa with her zoologist parents.
Cady is entirely unfamiliar with the American high school system, and she gets sucked into the world of “The Plastics,” a trio of popular girls led by the vicious Regina George (Rachel McAdams), after initially befriending two social outcasts, Janis (Lizzy Caplan) and Damian (Daniel Franzese). Originally intending to sabotage The Plastics from the inside, Cady instead becomes more like them, leading to several comedic and dramatic occurrences as she navigates the complicated social environment. Throughout the film, Cady discovers essential truths about herself, her friends, and the value of being herself.