Lindsay Lohan's career began when she was just a toddler in modeling, but by the time she was ten, she landed a lead role in Disney's remake of The Parent Trap. From there she starred in other Disney Channel original movies and even had a small music career with two albums in 2004 and 2005, respectively. Her career, though, has been defined by being a child star turned out-of-control celebrity for many years since her first arrest in 2007 for driving under the influence of alcohol. She subsequently struggled with drug and alcohol addiction, which resulted in her going to rehab a total of six times. In recent years, however, she has faded from the public eye since taking a step back from Hollywood and now currently resides in Dubai. More recently, she has made appearances in movies, signing a two-movie deal with Netflix, per Deadline, along with rumors fueled by her and Jamie Lee Curtis of the potential for a Freaky Friday sequel.
In her heyday, Lohan was teen pop royalty, but ultimately faced the same public downfall as many other early-2000s teen idols did at the hands of tabloids. Nevertheless, public opinion has changed in recent years over the unfair treatment of celebrities, especially young women celebrities, and with that has come more sympathy for stars like Lohan. Besides all of that, Lohan is still well-known for her teen comedy movies, some of which have become iconic classics still loved by many today. So, we made a ranked list of her best comedy films to date.
4 Confessions of a Teenage Drama Queen
Based on a novel of the same name by Dyan Sheldon, Confessions of a Teenage Drama Queen is a teen musical comedy released in 2004. Originally starring Hilary Duff before she dropped out of the film, who, in turn, handed the lead role of Lola off to Lohan. The role that would win the actress a Teen Choice Award for Breakout Movie Actress and while it's not her most memorable or beloved role, it established Lohan as a teen icon. The film, like most teen comedy movies, didn't do well with critics, but its outlandish and over-the-top humor and musical numbers have a charm that a lot of teen comedy movies just don't have. It's lovable and easy to consume plus relatable to many other pre-teens who've had to deal with moving to a new city and away from the life you might've loved before.
3 Freaky Friday
It's hard to find anyone that doesn't love Freaky Friday. The movie stars Jamie Lee Curtis and Lohan as bickering mother and daughter who can never see eye to eye, but when an intrusive woman working at the Chinese restaurant they're visiting puts a spell on them, they wake up the next morning swapped into the other's bodies. Both actresses give hilarious performances while also reflecting the disconnect between generations. The movie garnered a lot of success and praise, as well as adoration from many, since its release in 2003 and even inspired a horror-comedy, Freaky, which follows the same premise, except instead of mother and daughter, it's murderer and victim. The movie has stuck so much with audiences for years that the buzz of a potential sequel has made the internet very excited to see the two actresses return as mother and daughter to bring us laughs one more time.
2 Mean Girls
Probably Lohan's most well-known work is her role as Cady in 2004's Mean Girls. It was released just a few months after the release of Confessions of a Teenage Drama Queen, but couldn't have been any more different from the Disney film. To say that Mean Girls is a staple of the early-2000s is an understatement. The movie not only went on to inspire other teen movies, but also became a pop-cultural phenomenon. In 2016, Esquire named Mean Girls one of the most quotable movies of all time, which we can all say we've quoted Mean Girls at least once and that can probably be true for anyone that chose to read this article. Lohan has been so closely tied to the movie that you can't possibly think about one without the other coming to mind. And with the film still being as timeless and adored as it is nearly two decades later, it ensures that no matter what happens to Lohan in the future, she will always be remembered for Mean Girls.
1 The Parent Trap
While The Parent Trap isn't as widely adored or a cultural phenomenon as Mean Girls, it's still one of the best films in Lohan's career and, with the amazing acting, has some of the funniest scenes from a Disney movie. The film was released in 1998 as a Disney remake of the 1961 film of the same name based on the book, Lottie and Lisa, written by German writer Erich Kästner. It follows twin sisters who were separated because of their own parent's separation and growing up with entirely different lives. Until they accidentally bump into each other and discover the truth, and now want to try and get their parents back together. The film was Lohan's first lead movie role and would be the beginning of a successful career. When the movie was initially released, she received praise for her shining performance as the twin sisters and was even called the "soul of the film" by the Los Angeles Times, possibly helping the remake outshine the original. Her charm mixed with the funny hijinks of the sisters' plans against their father's fiancée and their mischievous way of getting their parents back together made for one of the best watches of a Lindsay Lohan comedy movie.