Her career began at the early age of three, as a model at the Eileen Ford Agency, making appearances in over 60 television commercials for clients such as The Gap, Pizza Hut, Wendy's, and Jell-O. Her acting debut came in 1996 with the role of Ali Fowler in the TV drama Another World.
She only kept moving forward from this point, starring in the Disney remake of The Parent Trap (1998). She gained widespread recognition and a Young Artist Award for Best Leading Young Actress in a Feature Film, as well as Blockbuster Entertainment and YoungStar award nominations.
Lohan returned to the world of television after signing a three-movie contract, starring in the made-for-TV movies, Lifesize (2000) and Get a Clue (2002).
Feeling ready for a short break from acting, she went on to pursue her musical interests and made a five-album production deal with Estefan Enterprises in September 2002, and signed a recording contract with Casablanca Records.
A month previous to this deal, she was cast to star alongside Jamie Lee Curtis in Disney's Freaky Friday (2003). Critics and audiences around the world agreed on the greatness of Lohan and Curtis's performances.
In 2004, Lohan made two movies: Confessions of a Teenage Drama Queen (2004) and Mean Girls (2004). Mean Girls really solidified her position as the big teen star of the time. She received four awards for her performances in Freaky Friday and Mean Girls at the 2004 Teen Choice Awards, as well as two awards at the 2005 MTV Movie Awards for her performance in Mean Girls.
Lohan and fellow actress, Raven-Symoné, moved in together in Los Angeles for some down time between projects. She dated pop star, Aaron Carter, for a little while on the side as well.
She went on to host Saturday Night Live three times between 2004 and 2006. In 2004, she became the youngest host for the MTV Movie Awards, at the age of 17. And in 2006 she hosted the World Music Awards.
Her 2004 debut album, Speak, also earned her much attention, hitting number four on the Billboard 200 as well as reaching Platinum certification by early 2005.
Her rise to stardom during these years made her a prime target for the paparazzi, which made her love life and partying a large topic of discussion and gossip in the public. "I don't even know how to take a break, because I go crazy. I just sit in a room and I don't know what to do. I went to the Metropolitan Museum and just sat there. But they didn't take any pictures of that, which sucks, because that would have been more interesting than pictures of me coming out of a club."
In 2004 she began dating Wilmer Valderrama, which led to her guest starring on That '70s Show, on which he starred. Their breakup caused some problems for her during the shooting of the Disney movie, Herbie: Fully Loaded (2005). "Wilmer Valderrama was my first love. But the timing was bad. And there were all these girls around; he would flirt with them. And I couldn't handle that. I really didn't trust him. So that was hard, too."
She continued with her music as well, releasing her second album, A Little More Personal (Raw), which also did well for itself, becoming certified Gold.
In 2005, Lohan's parents legally separated and finalized the divorce in 2007. She felt really hurt by the whole process, especially since her father put the family through much pain throughout her life.
She went on to star in some smaller, independent films such as A Prairie Home Companion (2006) and Bobby (2006). However, her intense partying didn't slow down, and her career was beginning to collapse as a result. Studio executive, James G. Robinson, called her out saying that she was very unprofessional, showing up late to sets if she even showed up, and that they all knew that it was because of her out of control partying.
In 2006, she began attending Alcoholics Anonymous meetings, and then during the shooting of I Know Who Killed Me (2007), she had appendix surgery and then shortly after checked into rehab, which put the production on hold for some time.
She continued to lose roles and drop out of productions as she struggled with her personal problems. She got into a car accident and received a DUI four days before production began for the film, Poor Things. The film was put on hold as she went to rehab. Upon coming out, she was given a SCRAM bracelet to monitor her sobriety, and then three weeks before production resumed, she refused a sobriety test and was taken to the police station, where it was found that her blood alcohol level was above the legal limit. In addition to driving under the influence and driving with a suspended license, she was also booked with possession of cocaine. She was then sent to rehab for a third time and was replace in the production of Poor Things. "It's so weird that I went to rehab. I always said I would die before I went to rehab."
In May 2008, she made her first screen appearance since I Know Who Killed Me (2007) on the ABC TV series Ugly Betty. She guest starred in four episodes during seasons 2 and 3.
She kept building on this momentum by starring in Labor Pains (2009), but instead being a theatrical release, it went straight to TV, which proved to be a little anti-climactic for her.
Lohan gave money to the British Red Cross in March 2010 after the earthquake in Haiti. That same month, she went into legal proceedings for $100 million against the company, E-Trade, for a TV commercial, which she claimed used her likeness without her permission. The matter was settled privately in September.
She then narrated and presented the British TV documentary, Lindsay Lohan's Indian Journey (2010), which covered the topic of human trafficking in India.
In May 2010, Lohan was replaced in her role in the film, Inferno, due to court-mandated rehab. Furthermore, she missed a mandatory hearing because she was at the Cannes Film Festival, which resulted in drug and alcohol classes, wearing an alcohol monitoring bracelet, and random drug testing. After missing some classes and meetings, she was sentenced to 90 days in jail. She was released after 14 days due to a combination of overcrowding and the nature of her crime. From there she went to rehab once again and was released after 23 days, but had to submit to random drug and alcohol screenings as well as attend therapy.
Lohan starred in Machete (2010) for which she didn't get the best reviews. That was followed by her failing another drug test and going to jail. She was released on bail, and once again, went to rehab.
She did a photo shoot for Playboy in 2012, which, according to Hugh Hefner, broke sales records.
She hosted SNL for the fourth time in March 2012, which was met with mixed reviews. She also appeared on the show, Glee.
She starred in First Point (2012) and Liz and Dick, which is set to premiere November 2012.
She has also been working with The Canyons and Scary Movie 5 which are set to release in 2013.